FIRE'S DISCOG DIVES: Olivia Rodrigo

 

FIRE'S DISCOG DIVES: Olivia Rodrigo

What’s up guys, welcome back to Fire’s Flaming Hot Takes, and I told you that I was gonna do a discog dive in my 1991 worst list, and the hint I gave you was that they were on Bizaardvark. If you guessed it would be Jake Paul, go see a doctor. Yup, it’s Olivia Rodrigo!!

This...might’ve honestly been more difficult to assemble than my Kacey Musgraves discog dive. I was honestly surprised by this at first. Kacey has 163 songs to her name (at the time I wrote that article) if you count her demo albums from the 2000s (which I do). And TOTC posted a tweet before she had released her latest album suggesting that Olivia only had 31 songs as a recording artist. But the key phrase here is “as a recording artist”. And that’s when I realized that if I counted Kacey’s 2000s demo albums in her discog dive, I’d also have to treat the songs Olivia’s released as part of Disney for her discog dive. And that created a really weird situation where songs I know she sang in her shows weren’t credited to her at all on Spotify or RYM. Particularly for High School Musical: The Musical: The Se-okay no, I need to acronym this or else it’s gonna be an utter headache to write this article...so let’s go with...HSMTMTS...I’m aware it reads a lot like Drake trying to speak Welsh but fuck you I have a HSMTMTS to talk about. But anyways, for HSMTMTS, there were songs I know she sang in the show but weren’t credited to her but instead the entire cast. The simple fix would be to include songs credited to the entire cast in this ranking, right? Well...no. The problem is that Rodrigo transitioned from a main character to a recurring one in the 3rd season before leaving the show entirely for Season 4. And when I was stuck trying to rank “Get’cha Head In The Game” among the Olivia songs even though she wasn’t present at all for that number, I realized that this would simply be too much. And I also realized that wait, I didn’t count Texas Two Bits’ album for my Kacey Musgraves discog dive (I forgot), why should I count songs credited to the entire HSMTMTS cast? So with much deliberation, I’ve ranked every single song Olivia Rodrigo has released from worst to best to celebrate the fact that I’m seeing her live in December!! It cost nearly $800 so you better deliver Olivia (only half-joking, no pressure), I literally paid less to go to The Eras Tour!!

So with all that, what’s eligible for this ranking? Well, I’m counting anything that’s listed in Olivia’s discography on RYM, excluding anything that is nothing more than a remix of one of Olivia’s songs. However, acoustic versions will count for this ranking. I’m also not gonna be including anything from Olivia’s live albums. Also...no instrumental tracks, because come on! And the HSMTMTS songs are excluded unless they are explicitly credited to her. This does mean we’ll lose out on some genuinely great songs like “Born to be Brave”, but I need some structure here. And if I accidentally miss a song...again, I sowwy. This leaves us with 70 songs to get through and I already have some other ideas for articles I wanna do this summer as well as some IRL stuff stacking up, so I’m gonna try to keep my reviews pretty brief. Keep in mind that this ranking is obviously not final, I’m sure some of these songs will shift around pretty wildly and obviously Olivia is still making music. I’m not gonna be updating this, so this ranking is as of June 22, 2026. So with all that in mind, how has Olivia’s artistry, sound, and career evolved over the years?

Olivia started out on Disney in 2016 when she played Paige on Bizaardvark. And let me tell you, Bizaardvark is a fitting title because every single fucking thing that happens in this show is fucking mental. No other combination of quantum particles can come together to make anything close to that. When Olivia Rodrigo rapping at least 6 times throughout the show doesn’t even crack the top 30 weirdest things about it, in comparison to...

...I think that says it all. It’s also just a sight to behold how quickly the show turned from pretty entertaining into one of the most brain-rottingly awful shows I ever watched. Just saying, any show that makes me unironically think “I miss Jake Paul” is doing something very wrong. But arguably the show that actually launched Rodrigo to fame was her starring as Nini on HSMTMTS. Full disclosure, I first watched that show way back in 2021, when Rodrigo became the biggest name in music overnight and I thought it fell off badly after she left the show. Upon rewatching it, it’s definitely not anywhere near as bad as I thought it was at the time, but there’s no denying that when Rodrigo left, it just didn’t hit the same. Nini was a main character, and her not being in the show anymore is like if in Aladdin, all of a sudden Prince Ali was some other street rat while Aladdin just got killed off in the middle of the movie. But after HSMTMTS earned Rodrigo her first charting entry on the Hot 100, peaking at a very low #90 in early 2020, it was whiplash-inducing when she became an A-lister in 2021 with her debut album SOUR, a vulnerable, if one-dimensional, breakup album that promised real potential going forward. She teetered the line between ballads and rock bangers effectively, leaning more into her rock side for GUTS culminating in what’s as of writing her latest album, you seem pretty sad for a girl so in love, a concept album that takes the vulnerable songwriting of SOUR and pairs it with her rock side off of GUTS for her most mature album to date. If there was any word I’d use to describe Olivia Rodrigo’s discography, it’d be consistent. She doesn’t hit the same highs as Kacey Musgraves for me—her highs are more comparable to Taylor Swift’s—and she avoids hitting the lows of Taylor’s worst songs. So with all that finally out of the way, let’s get this ranking started with our one song in the bad tier!!

 THE 4/10s - BAD TIER

70. Blobfish w/Madison Hu

Bizaardvark featured a number of sketches, and “Blobfish” was one of them. And...this just sucks. The punchline is that it’s a love song to a blobfish because blobfishes are ugly...good for it? But this just isn’t a very good joke. You can swap blobfish out for squid, octopus, or hell, angler fish and this song would still be the exact same. The sketches in Bizaardvark were always really disconnected from the plots of the episodes so I can’t even say this works in the context of the show! Of all the sketches from this show to be put on streaming, why did this have to be selected? “So Dramatic” was RIGHT there, that’s actually inspired! I love you Olivia, and I know you were like 13 when this was made, but this is the kind of shit that would get you bullied. Good for the blobfish, but this is bad.

 THE 5/10s - MEDIOCRE TIER

69. The Bels

I feel bad for this—Olivia was 5 when this archival release was recorded and it’s hard not to feel that this was a home video that wasn’t meant to see the light of day. I get how someone could find this cute—it’s why it’s not in the bad tier—but as music, this isn’t very good. Olivia sounds like the average 5 year old—which is to say she sounds like a little kid singing offkey at her Kindergarten Christmas assembly. And the production is weak too—it sounds like a Destiny’s Child reject and there isn’t anything Christmas-y about it. This was a home video (or I guess home audio?) that Olivia released via a newsletter email attachment. It was never meant to be judged as a polished song. Again, I’d feel too mean if I called this bad, but I’m certainly not gonna call it good either.

 THE 6/10s - DECENT TIER

68. Bizaardvark Theme Song w/Madison Hu

The theme song to Bizaardvark, and it’s...alright. Look, by nature, theme songs, especially to Disney shows, are mostly gonna work best in the context of the shows. Save for “Time Of Our Lives” from I Didn’t Do It or “The Best Of Both Worlds” from Hannah Montana, these Disney theme songs don’t really stand on their own. And thus, this song, which is literally called “Bizaardvark Theme Song”, can’t stand as its own entity. In the context of the show...it’s sure a theme song alright. It’s expositional fodder to introduce the main characters—Amelia of Perfect Perfection, Dirk of DareMeBro, and Bernie of...literally no channel (it makes sense if you’ve seen the show lol). It does exactly what it sets out to do. It just doesn’t accomplish anything as a song on its own.

67. Bop to the Top - Nini & Kourtney Version w/Dara Reneé

If “Born to be Brave” was credited to Olivia, it absolutely would’ve been in my top 20. As is, this is a very short song, clocking in at 35 seconds and I somehow cannot hear Olivia at all. In fact, it sounds more like the original High School Musical song. Ashley Tisdale and Lucas Gabreel are way more prominent...so it’s decent? If only because I like the original song.

66. I Think I Kinda, You Know - Just for a Moment Mashup (From “High School Musical: The Musical: The Series”) w/Joshua Bassett

Full disclosure, in my research for this article I actually listened to Joshua Bassett’s Khia ass response songs to Olivia Rodrigo in 2021 and they soured me on this guy in record time. He looks like a Mormon Benson Boone (so basically like Benson Boone). That said, I can’t lie, in HSMTMTS he had some bangers. This isn’t really one of them, but I can hear how much Joshua Bassett and Olivia Rodrigo were in love with each other at the time and their chemistry does elevate this to being decent. That said, it feels kinda generic. It takes the strengths of the two songs and instead of letting them build off each other, it cancels them out into this borderline stomp clap composition.

65. YAC Alma Mater - Nini Version

In HSMTMTS, Nini joins the YAC, leaving the East High drama department behind and is feeling torn on her decision because she feels pigeon-holed. This song does a pretty good job of capturing that initial tension as Olivia sings the YAC anthem. She’s a great actress and the tension comes through in her delivery. But this is a song that really only works in the context of the show. On its own...it just sounds like a commencement ceremony. Nothing wrong with that, but it’s the type of song that only works if you’re literally a student at the YAC—which isn’t even a real school—so this just doesn’t have much use outside of the show.

Now for the stuff I actually like!!

 THE 7/10s - GOOD TIER

64. girl i’ve always been

One of the bonus tracks on GUTS (spilled), it’s easily my least favorite of the bonus tracks for really one simple reason—the twang is just...distracting. I like the instrumentation a lot, the acoustic guitar-driven groove does a lot to help Olivia’s twang feel like it reinforces the song. But the song just hits a bit...oddly. If this was released in 2010, it probably would be heard as a parody of Ke$ha. That’s really what this reminds me of—it sounds like if early 2010s Ke$ha made an acoustic guitar song. And I kinda struggle to discern what level of irony this is all on. It feels like Olivia both knows and doesn’t know how ridiculous it sounds. Still, it’s funny enough for me to like it.

63. I Think I Kinda, You Know - Nini Version

In the first season of HSMTMTS, Nini posts this song on Instagram as a love song to Ricky and he doesn’t say “I love you” back, triggering a breakup and leading to the messy love story the two would go through the rest of the series. And that context makes it work especially well in the show, but it’s also sweet enough of a love song to work as a simple love song on its own merits, especially paired with that warm acoustic guitar (or is it a ukulele?) melody.

62. I Think I Kinda, You Know - Duet w/Joshua Bassett

Fuck you Joshua Bassett. Okay, all jokes aside, this is pretty much here for the same reasons that the Nini version of this is also in this tier. I like the fact that it’s a duet—it reinforces that both partners feel this way about each other, which strengthens the song. The added verse from Joshua Bassett fits the storyline really well because in the show, Ricky didn’t say “I love you” because he didn’t know how to. He says in the song that he knew what to say but the words went away when he opened his mouth, and it fits his character arc throughout the series. And I guess I have to praise Joshua Bassett more because...

61. Just for a Moment w/Joshua Bassett

I don’t know what to say, Joshua Bassett and Olivia Rodrigo have really good chemistry for a really cute love song. What elevates this above “I Think I Kinda, You Know” is the swell on the chorus as the production starts to lightly build up. In HSMTMTS it’s positioned as the point where Ricky and Nini separately realize their feelings for each other. Nini thought she fell out of love with Ricky but is unsure now. The song is very specific to the plot but still feels broad enough to work on its own even if on its own, it’s a bit generic—hence why it’s just good.

60. The Best Part

Honestly there’s very little distinguishing any of the HSMTMTS songs the past few entries. They’re perfectly pleasant and lovestruck but they don’t really stand out much in any way.

59. happier

This has always been one of my least favorites on SOUR. Not that it’s bad—not remotely, but it’s an instance where the teenage-ness of the album actually works against the song. I absolutely get the angst of your ex moving on with a new partner who seems to be everything you aren’t and hoping that your ex isn’t happier with them than they were with you. Especially when you’re clearly not over it yourself. This could’ve easily been utterly insufferable, but Olivia’s self-awareness saves this. She openly admits that she’s selfish and that she knows she’s tearing his new girlfriend apart as if that’ll make her ex miss her. The production is also a tad too dramatic which is why it doesn’t quite hit being great. That said, it’s honest and self-aware about how bad the angst is, so it’s pretty good.

58. enough for you (piano version)

Full disclosure, this seems to be a vinyl exclusive that I’m not sure made its way to streaming so I’m just gonna have to rely on the performance in the driving home 2 u (a SOUR film) documentary (it sounds like a studio recording and it’s played on a piano so it’s probably the closest I’m gonna get). I was shocked by how much I really liked “enough for you” when revisiting SOUR for this article and I’ll get into why when we get there later on in this ranking. But I just don’t quite think this version cultivates the same atmosphere as the original.

57. Let It Glow - From “Frozen Northern Lights” w/Madison Hu

I spent 20 minutes trying to find the episode this was used in and I didn’t get anywhere outside of seeing a very cringeworthy episode of the show that wasted 20 minutes of my life. But anyways...from what I can tell, this is Paige and Frankie from Bizaardvark providing a weird crossover song for LEGO Frozen. And it absolutely is a kids’ song. Olivia Rodrigo and Madison Hu explain how northern lights work. And in that regard, this is much better than it has any right to be. The pulsating synths that call back to the early 2010s sound great and hell, even when they rap they ride the beat shockingly well. This would’ve probably ended up in the great tier if the synths had just a tad more oomph to them and if...you know, it was longer than 1:19.

56. logical

I remember in 2023 in the Pulse Discord server when the “2+2=5” lyric was getting dunked on. And I’ve always thought that that lyric was intentional to build to the punchline that love is never logical and how the breakup left her feeling stupid. It’s not one of my favorites on this album, but I like it all the same.

55. hope ur ok

This used to be my least favorite on SOUR. I always thought it was good, but it felt like the least memorable song on the album. And yes, I still stand by it being the least memorable song on the album—it also has possibly the clunkiest production with the guitar being drowned in way too much reverb. But the standout here is the lyrics. It’s the point on the album where Olivia finally accepts that her ex has moved on and just hopes he’s okay. If “happier” was the bargaining stage of the 5 stages of grief, this is acceptance—it almost feels like a reverse of “happier”, where instead of hoping her ex won’t be happier with his new partner than he was with Olivia, she wishes him the best with no strings attached. Yeah, this is one that’s gotten better with the benefit of time.

54. Granted

In HSMTMTS, this song plays when Nini is on the bus back to the YAC. She’s second-guessing if she should go back or stay behind in Salt Lake. She’s asking herself if she’s taking her acceptance into the YAC for granted and she doesn’t want to have regrets whatever decision she makes. Olivia sells the tension at the core of the song perfectly and the music is really strong too. The production subtly swells on the chorus with the smolder of the electric guitar. Yeah, it’s a really good song—very close to great. And that neatly segues into...

Now for what’s actually great!!

 THE 8/10s - GREAT TIER

53. lacy

This is another one that got better over time. I thought it was just pretty good when I first heard it, but on relisten, the queer subtext made the song much more interesting—it teeters a very thin line of the envy that was present in the background of SOUR and queer infatuation. But what really won me over here was the way the production starts building up around the last minute of the song. The backing vocals sound great as the guitar strumming becomes heavier. The first ⅔ of the song being more spare and intimate helps that last minute feel like a satisfying climax.

52. teenage dream

No, it’s not better than the Katy Perry song, but Olivia’s “teenage dream” is still pretty great for what it is. It feels like it’s heavily influenced by Billie Eilish’s “Happier Than Ever”—with the way the production picks up more of a rock edge during the last minute. And it’s not better than that song, but I think the lyrics help this a lot—capturing that fear of losing the best parts of yourself as you grow older. It captures exactly why growing up is so terrifying.

51. enough for you

Yet another grower for me!! The lyrics are what ultimately elevated this for me. This lyric in particular feels so vulnerably devastating:

“And you always say I'm never satisfied, but I don't think that's true

'Cause all I ever wanted was to be enough for you”

The guitar enhances that vulnerable atmosphere. That makes the subtle flip of the chorus in the outro a well-earned bit of hope to hold onto:

“And they'll think that I am so exciting

And you'll be the one who's crying

Yeah, you always say I'm never satisfied, but I don't think that's true

You say I'm never satisfied, but that's not me, it's you

'Cause all I ever wanted was to be enough”

50. Love the Haters w/Madison Hu

Okay yeah, the Bizaardvark sketches that made it to Spotify are pretty cringe, but while “Blobfish” was just embarrassing, “Love The Haters” is charmingly cringe to me. It’s a simple, cliche song about “loving the haters”. But while other songs in this vein tell you to “kill ‘em with kindness” or to “shake it off”, this song actively tells you to listen to constructive criticism while acknowledging that you can’t please everyone. The first verse conveys the former and the rest of the verses show you what happens if you try to be a people pleaser and satisfy everyone, turning it into a hilarious monogenre clusterfuck of autotune, country, techno and...trans icons?

“This guy says, ‘Girls stink’

We're dudes now”

Also for what it’s worth, the Radio Disney-coded acoustic guitar driven synth chords that lead the first part of the song sound pretty great. Yeah, this is really funny and cringe in a charming way.

49. Even When/The Best Part w/Joshua Bassett

This song makes most sense in the context of HSMTMTS and once it gains that context, it doesn’t lose it. In the show, Ricky and Nini, now back together and doing long-distance, record a voicemail to each other at the same time with a song that happens to be the same chords and melody. It’s a mildly amusing coincidence, but it highlights just how much chemistry Joshua and Olivia have. It feels like they’re really singing this to each other. In other words, this is a mashup that actively elevates both songs.

48. making the bed

It wasn’t even until writing this very review that I realized that this was Olivia’s “mo money mo problems” song. I just thought the noise guitar breakdown near the end of the song sounded great. But this entails Olivia lamenting the people she pushed away after she became famous. That lyrical theme and Olivia’s delivery justify the arrangement being so big.

47. The Comeback Song w/Madison Hu

Quite frankly, this is the most G-rated song I’ve ever heard, and paradoxically, it’s honestly my favorite Bizaardvark song. Yeah, the trap beat sounds pretty generic and Olivia and Madison’s rapping is rather lousy, but what makes this work is that they seem to be aware that it sounds awful and are just throwing themselves into it wholeheartedly. The punchline is clear and simple—Paige and Frankie claim they are so good at comebacks...but only hours after it would’ve hit hardest. It’s definitely relatable, possibly the most universally relatable topic ever, but the fact that it sounds so obviously bad and they’re just embracing it makes it work. I’d like to think that if Olivia and Madison wind up in a Kendrick-Drake-esque beef, their tactic would be waiting a year after the opponent’s diss track drops to drop theirs.

46. stranger

This was always really charming to me. It’s the point where Olivia finally moves on from the breakup and now her ex is just a “stranger she knew everything about”. The guitar sounds super cozy and helps this feel really cute!

45. jealousy, jealousy

Olivia’s ANGRY. All jokes aside, in driving home 2 u (a SOUR film), Olivia expressed that she wrote this song about her unhealthy relationship with social media. It’s a very high school song, as is SOUR as a whole, but honestly I can relate. I spent more time than I should’ve in high school scrolling on Instagram and seeing peers living their best lives. It didn’t really click in my mind that of course Instagram is gonna make everyone’s life look amazing because why would you willingly post the worst moments of your life online? Still, it absolutely can distort your view on your own life and make you envious of what others are doing that you aren’t. And the high school framing makes the trudging guitars intensify the anger. It’s not a cathartic song, but it’s not trying to be. It’s more so letting the anger simmer slowly. I will say that if this actually had a cathartic release, it probably would’ve knocked this up into my 9/10s, but this is still great.

44. What I've Been Looking for (Nini & E.J. Version) w/Matt Cornett

This is definitely a song that works best in the context of HSMTMTS. At this point in the show, Nini had just found out that E.J. had betrayed her by looking through her phone so she forced smiles her way through the number. You can really hear the fact that Nini genuinely wants to kill E.J. in this. And that makes it kinda funny, considering that the original song in the High School Musical series was supposed to be a sincere love duet.

43. The Rose Song

This song is also from HSMTMTS, but I’d argue that unlike the other songs from the show in this ranking, this actually works best out of the show’s context. In the show, the drama students are performing Beauty & The Beast and Nini is tasked with writing a song for the rose. And that’s my main issue with this song—it feels like a song about Nini more than the Beast’s rose. As someone who’s done two school productions of Beauty & The Beast (funnily enough both times I was cast as Cogsworth) and considers the original movie one of the all-time best Disney films, the beast doesn’t view the rose as anything but a reminder that he’s running out of time to find true love. He doesn’t “love” the rose. It would require a fundamental rewriting of the entire story for this song to fit Beauty & The Beast. I can say all that while acknowledging that the song genuinely sounds great though—Olivia’s vocals are stunning and she makes you believe that there are more sides to her than from our point of view. The production is dramatic in the right ways to create an engaging atmosphere that swells up throughout the song before the outro stripping everything back to leave Olivia’s vocals front and center. So yeah, this is a great song, but I have to side with Ricky on this—there’s no way Nini wrote this song from the point of view of the rose.

42. Wondering - Ashlyn & Nini Piano Version w/Julia Lester

In HSMTMTS, Ashlyn, cast as Ms. Darbus is tasked with writing a power ballad for her character. Unlike with “The Rose Song”, I can buy this fitting into High School Musical since we don’t know much about Ms. Darbus’s past. In the show, Nini walks in on Ashlyn practicing the song on the piano and starts singing it with her. Julia Lester and Olivia sound great together with impressive vocals and great harmonizing. Great track!!

41. Wondering w/Julia Lester

This is basically exactly the same as the piano version other than maybe a few string touches. And being bluntly honest, I can’t remember what the context of this song was in HSMTMTS. So really, you can copy-paste from the previous entry here. It’s basically a tie.

40. All I Want

What a weird point in time when this peaking at #90 in 2020 was Olivia Rodrigo’s biggest claim to fame. Seriously though, “All I Want” is great, it works in a way that the great 90s AC staples work—great vocals that support the production and enough going on in the production to not feel generic. Great song!

39. You Never Know

I suppose this is a bit of an edge case to my criteria because this is credited to the entire HSMTMTS cast and not Olivia on Spotify, but RYM credits it to her. So I’m just gonna include it in this ranking. Season 3 of the show is the start of Olivia’s departure from the show. Nini goes from a main character to a recurring character in this season before being completely written out of the show in Season 4. As such, this feels like Nini’s swan song. And damn, what a note to go out on. The song is about Nini turning 18—a turning point for her as she decides to pursue a music career leaving behind the East High drama club. The verses being more understated leading into that powerful chorus creates a very bittersweet tone that perfectly fits how this song plays in the show, when Nini is reminiscing on her journey with her friends in the East High drama club. Olivia absolutely sells this bittersweet hope so well. Hell, if this wasn’t attached to Disney, this could be a high school or even college graduation song!! Sure as hell would beat out my older cousin’s college graduation song being fucking “Best Day Of My Life” by American Authors haha.

 

38. Can’t Catch Me Now

The easy comparison for this is Olivia Rodrigo making a Lizzy McAlpine/Phoebe Bridgers song. And it’s not like it’s wrong, but I think that comparison dismisses just how hauntingly beautiful Olivia’s delivery is here. Olivia’s reverb-soaked delivery sounds great against the chamber pop production. The way the song builds up leads into that bridge where her vocals are front and center and effectively match the dynamics of the production. I won’t deny that this isn’t a very accessible song, but I can and will say that it’s great all the same.

37. the grudge

I’m very inclined to call this a diet “drivers license”—with the devastated belting, the piano line, and the fact that they have similar production dynamics. But considering “drivers license” has long been one of my favorite Olivia Rodrigo songs—and yes we’ll get to it way later in this ranking—an only slightly weaker version of it is still great. Olivia sells the heartache really well here. It might be a bit of a retread of what was done on much of SOUR, but it’s a retread that still captures most of the magic of the original work.

36. get him back!
I’ve always loved Olivia’s conversational cadence on the verses—she has the perfect attitude to make it work. But I will admit that I’ve always been left feeling like I should like it way more. Something about the singalong chorus just doesn’t quite land the way it should. It feels like it’s trying a tad too hard to be a singalong moment instead of letting the catchiness work seamlessly with the actual song. That said, that bridge is peak—the increasingly unhinged delivery with the equally unhinged lyrics just works perfectly. Starting with keying his car to ending with kissing his face with an uppercut and meeting his mom just to tell her her son sucks is just psychotic in all the right ways. Great track!!

35. vampire

This works way better than it has any right to. The lyrics are definitely overwritten in a Christina Perri vein and the pivot to more fast-paced production at the 1:19 mark feels a bit sloppily executed. But what’s always made me really like “vampire” is Olivia’s genuinely stunning delivery, nailing the high notes and still selling the heartache as well as ever. Not my favorite from GUTS nor what I would’ve chosen for the lead single, but it’s still really damn solid all the same. Also shoutout to 2023 New Year’s Eve when my best friend sang this at our little karaoke night, nailed it, and then me trying and failing to DM Olivia the video of her doing it on Instagram (Olivia if you’re reading this please authorize me to send you more messages so I can send that video to you 😭).

34. deja vu

If her performance of it in driving home 2 u (a SOUR film) is any indication, “deja vu” is a song that’d most likely sound best live. It admittedly took me a while to find “deja vu” truly great (I’ve always thought it was good though) because as an audio file, the drums just don’t sound very good. But it was watching that driving home 2 u (a SOUR film) documentary and seeing how it would likely sound live that convinced me that this is a banger. I will admit that it’s not a song fit to be overplayed on the radio as it does get tiresome, but in small doses, it slaps. Fun fact—according to the documentary, apparently Olivia thought people were gonna hate this song and was second-guessing releasing it as a single as soon as two days before its release. At least we proved that she was wrong by making it one of the biggest songs from that album!

33. obsessed

What makes “obsessed” work is that it knows it’s insecure and embraces it. Olivia says she’s obsessed with her partner’s ex and she absolutely gives every indication that she is. She looks at her pictures so much you’d think they were friends. She knows her star sign, every movie she’s been in, and her fucking blood type!! She could say she knows her social security number, her bank account password, and her drivers license expiration date at this point and I don’t think I’d be shocked. Either way, any song that uses the word “butthurt” unironically and somehow makes it work is clearly doing something right.

32. brutal

I once said that I didn’t fully love this because it felt too much like an angsty teenage temper tantrum without much self-awareness. In 2026, I’m not too good for an angsty teenage temper tantrum without much self-awareness. And honestly, my point that there’s not much in the way of self-awareness was objectively incorrect. The lyrics themselves describe the self-awareness without explicitly saying it. These lyrics explain the self-awareness themselves:

“And I'm so sick of seventeen

Where's my fucking teenage dream?”

“I'm so insecure, I think

That I'll die before I drink”

“And I'm not cool, and I'm not smart

And I can't even parallel park”

And notice the pronoun is “I”. That says that she FEELS all these things, she isn’t necessarily saying she actually is all these things, just how she THINKS people perceive her. Which is honestly...way more maturity than I had in high school.

31. traitor

“traitor” was at one point my favorite song on SOUR. And yeah, it has cooled on me over the years, but I still think it’s a great song. Olivia’s teenage heartache and devastation backs up the admittedly dramatic sentiment of calling her ex a traitor for finding someone new after breaking up with Olivia. She’s definitely not asking for our sympathy here, and she sounds incredible on this track. Also, I have an audio file somewhere on my old computer of me covering the song and it was one of the last good recorded covers I did before my AVM rupture...so this song feels oddly bittersweet for me.

30. 1 step forward, 3 steps back

This might be a bit of a curveball to some—but I’ve always thought “1 step forward, 3 steps back” was a very underrated SOUR deep cut, even if I don’t quite love it as much as I did back in 2021. Part of it is that it’s got that very indie pop girl aesthetic that I had a huge weak spot for in 2020-21. But I also think Olivia sounds great here—she sells the vulnerability of being with an inconsistent partner. She’s openly admitted that she was very inspired by Taylor Swift, down to the title being a reference to Taylor’s favorite number, 13. And I can hear the Taylor all over this, like how the way she sings “masochistic” in a cadence that feels very Taylor. Hell, this honestly could be put on Lover and I think it’d fit in pretty nicely. I imagine this is an odd choice to call a highlight from SOUR, but it’s a heavily underrated gem that’s worth reconsideration.

29. The Book of Love

Not gonna lie, when I first saw this title, my first thought was “is this a cover of that one 1958 hit?”. It’s not, but it is a cover of a Magnetic Fields song. And honestly I think this is better. The original song has a very sparse arrangement that doesn’t help cultivate much of an atmosphere to complement the great poetry. This cover, meanwhile, is a chamber pop-soaked piece where Olivia’s vocals sound gorgeous against the guitar drenched in reverb. It helps cultivate a very immersive atmosphere. And I’ve recently learned that Olivia is a huge music nerd, down to doing an interview with Anthony Fantano recently. And this song is probably the exemplar of that fact. I genuinely hadn’t heard a Magnetic Fields song before I listened to the original song for this review, but I’ve heard of them as a reference point by critics in other reviews. So in my head I kinda filed them as a massive critical darling who only the biggest of music nerds listened to. And this cover shows that Olivia not only knows her stuff, but also that she likely has a lot of love for the original song and she knows she can’t fuck this up. The original is already great, and this cover is even better.

28. drop dead (acoustic)

I love the original song a lot (as you know if you’ve read my Chill Pick article for April) so I’ll go into more detail when we get to the original later on in this ranking. As is, “drop dead” has a very strong foundation so the acoustic version is also great. That said, it’s nowhere near as awesome as the original for the simple reason that the stripped down acoustic aesthetic doesn’t capture the fun of the original song.

And we’re finally at the stuff I truly love!!

 THE 9/10s - INCREDIBLE/EXCELLENT TIER

27. begged

I’ll talk about this more when I review the album in my Albums Around The Fireplace article at the end of the year, but Olivia’s album you seem pretty sad for a girl so in love is split in half—the “girl so in love” side and the “you seem pretty sad” side to create a clear narrative arc of a fading relationship. “begged” is the second song on the “you seem pretty sad” side and it’s one of the first signs that the relationship is making her feel sad. It’s a song where she’s begging for more affection from her partner while also feeling bad about asking for that. Olivia’s vocals are desperate and aching to sell the lyrics. Hearing her say that she’s “overwhelmed and underfed” but still clinging onto hope almost perfectly captures the feeling of desperately wanting things to work out in a relationship while realizing that it’s just...not working out. Not one of my favorites on the album, but this is still heartbreaking.

26. all-american bitch

Okay yeah, I may now finally find “brutal” great, but “all-american bitch” still feels like a better version of it. “all-american bitch” goes hard all the way down—the softer verses serve as a great contrast to the rock guitars unleashed on the chorus, where she lets loose on the expectations that she must be perfect. Hell, the way she belts on this song reminds me a bit of Alanis Morisette. It feels like “Bitch” by Meredith Brooks updated for the 2020s. And given how apparently Meredith Brooks’s politics are now...questionable, to put it nicely (according to Todd In The Shadows at least)...this song means we can write that song out of this timeline now (“Bitch” is great though), because this is a banger!

25. ballad of a homeschooled girl

This song is hilarious. As the title suggests, it’s basically about the stereotypical life of someone who’s homeschooled. It’s not trying to hide that it’s stereotyping—instead it leans into the stereotyping with that strong rock production. Every time she steps outside it’s social suicide. Every guy she likes is gay. She’s searching up how to talk to someone on the internet. It all just feels cliche in a way that actually works to its advantage. These are all signposts we probably would associate with someone who’s homeschooled. I also love when she says “Can’t think of a third line” and then scats at the end of the song haha. Only she can make it work thanks to the attitude she brings.

24. Out of the Old

In HSMTMTS, this song plays as Nini contemplates applying to the YAC. And yeah, “Out of the Old” is just an incredible pop song that I know I would’ve eaten up in the pandemic if I’d known it back then. That acoustic-driven groove feels very warm and Olivia sells her uncertainty really well. And the “eh-oh”’s hit the sweet spot of not feeling like a gimmicky millennial whoop while feeling comfortably cliche (I mean that as a compliment lol). It’s also written effectively to fit like a glove in the show but also work as a song on its own. From “yearbook memory” to the lyrics questioning if she didn’t pursue her wildest dreams, if they’d feel comforting as dreams. There’s a strange comfort in living a simple, ordinary life. At the same time, you might wanna chase something greater and find a purpose in your life by following your dreams, even if that means leaving behind that old comfort. Honestly, this fits even better as a graduation song than “You Never Know”!! It’s the type of song that could be put in any coming of age show about an aspiring singer and it’d work very effectively!!

23. Breaking Free (Nini, Ricky & E.J. Version) w/Joshua Bassett & Matt Cornett

This song appears in the season 1 finale of HSMTMTS, where the East High drama club is performing act 2 of High School Musical when Ricky, despite being TROY, chokes up mid-performance and runs off upon seeing his mom with her new boyfriend in the audience. He tells E.J. to go onstage for him leading to their performance of “Breaking Free”, where Nini and E.J. give the mic to Ricky, saving the show (this would never fucking work IRL—I say that as someone who did 5 school productions in elementary school and couldn’t go on for one of my scenes one year because of a costume issue). And I mean...it’s fucking “Breaking Free”—it’s always been one of my favorite songs from High School Musical and this version is generally the same. I do appreciate the recontextualization here from the original movie, where Troy is encouraging Gabriella mid-performance to this version, where Gabriella (and Chad, I guess) is the one encouraging Troy mid-performance. Probably an unintentional flip, but it still works.

22. River

This is from High School Musical: The Musical: The Holiday Special, the Christmas episode of HSMTMTS. The episode is more of a series of interviews with individual cast members. Each cast member sings a Christmas song and Olivia Rodrigo sings Joni Mitchell’s “River”. I don’t think it’s controversial to say that Joni Mitchell’s “River” is one of the best songs of all time as an achingly sad masterclass of songwriting. What Olivia’s cover reminds me of most is Luke Combs’s “Fast Car” cover from 2023—she clearly adores the original song a lot and knows that she can’t fuck it up. Despite there not being much of a twist or new idea to this cover, Olivia nails her performance with note perfect emotional control and stunning belting where it’s most effective.

21. good 4 u

“drivers license” may have been the life-changing smash that turned Olivia into a popstar overnight, but “good 4 u” is easily her biggest Hot 100 hit. I will say that this is very susceptible to overplay, but if you’re in the mood, this is such a fun time. It’s super anthemic, riding the pop punk resurgence in 2021 to make a flailing angry song where Olivia’s sarcastic hurt just drips off the page. I love how you can hear Olivia getting angrier and angrier as the song goes on—her great acting chops make this a particularly fun song to sing.

20. pretty isn’t pretty

I love the smolder of the electric guitars and Olivia’s exhausted yet angry tone to match the lyrics about struggling to meet unrealistic beauty standards. This could’ve easily fallen into cliche territory, like a lot of the self-empowerment anthems of the 2010s (even the good ones) do, but what I think elevates this song is that while most of those 2010s self-empowerment anthems were trying to plaster on a smile and pretend like everything is okay, Olivia doesn’t force a smile, she just acknowledges that “pretty isn’t pretty enough” no matter what you do, changing up your makeup, skipping cake on birthdays, nothing is enough. And honestly, I think that could be way more cathartic to young girls who might need to hear that than...say, Jax shrieking about how Victoria was made up by a dude.

19. love is embarrassing

This is a really fun new wave cut, from the melodic guitars to Olivia’s delivery that clearly shows that she’s having a ton of fun with this. Some of the lyrics are also just wild in the best way possible—she’s saying that when her ex found a new version of her she damn near started World War III. You can feel the meltdown coming from the song and it’s a ton of fun.

 

18. Start of Something New - Nini Version

This is easily my favorite song from HSMTMTS. And that’s not all that surprising to me—”Start of Something New” has been my favorite song from High School Musical since I first saw the movies. But what did surprise me is that when I watched the show and Nini sang this at her audition, I got genuine goosebumps. And being honest, those goosebumps translate to the song itself too—Olivia sounds fantastic here. If anything proved that she had the potential to be a huge popstar before “drivers license” even came out, it was this.

17. honeybee

Now on the new album, “honeybee” is the 3rd song on the “girl so in love” side. I love how even despite being so early on the album, Olivia is bracing for the worst with lines like:

“And I hope I never see what your face looks like going

A face I swear that I could spend my whole life knowing

Herе's to hoping”

That subtext really elevates this from being just a quiet declaration of love into something that feels haunting. I love the gentle backing vocals that remind me in a good way of Billie Eilish. It’s a genuinely beautiful song that serves as the peaceful field of flowers before...you get stung...if you get what I mean.

16. so american
If the early 2010s-Ke$ha persona on “girl i’ve always been” felt a tad distracting, then “so american” is Olivia putting on that persona and making it REALLY work. It’s basically about Olivia falling for an English boy who playfully calls her “so American”. And that triggers all the wedding bells in Olivia’s head. The Ke$ha comparison comes in the “la-la-la-la-la-love”’s. I also really love the sugar rush that’s the synthpop production—it effectively captures how it feels to be head over heels in love. Yeah, this is a real banger.

15. favorite crime

I was shocked by how much I truly loved this song when I relistened to SOUR for this article, to the point it’s my favorite non-single from that album. It’s very understated the first two minutes, making Olivia’s belting the last 30 seconds sound gorgeous, especially as she harmonizes with her lower vocals. The song uses great imagery of “partners in crime”, with terms like “willing accomplice” and “fled the scene” to describe just how much Olivia invested into this relationship and how deep the breakup cut. The song just wrings out so much devastation.

14. stupid song

The 2nd song on the “girl so in love” side of the new album and what’s being positioned as the next single. It doesn’t quite feel as euphoric as “drop dead”, but it still sounds really happy, with that drum machine and that rhythmically conversational bridge with the loudly sung interjections. It’s clear just how in love Olivia is with this guy. Not my favorite song on the album because I do think it could’ve afforded to have a more joyful melody, but it’s incredible nonetheless.

13. scared of my guitar

This is a really vulnerable and honest song about how Olivia’s scared of her guitar because she uses it to write about her most painful experiences and thus relive them. And she says that she can’t lie in her art the way she lies to her ex. It cuts right to the core of why writing or talking about your painful life experiences is so difficult. Olivia might be scared of her guitar, but she used it to create a fucking incredible piece of music.

12. expectations

The penultimate track to the new album, a very upbeat swerve in the “you seem pretty sad” side. It’s about Olivia seeking a rebound after the relationship at the core of the rest of the album ends, assuring that she’s got expectations now. The dance-punk production has got that wink at the audience that Olivia is likely gonna let go of most of her expectations when she meets the next hot guy she sees. The fact that she has to assure us that she’s NOT desperate for loving while he is makes me convinced of that assertion. Either way, this is a ton of fun!!

11. less

“less” is the point on you seem pretty sad for a girl so in love where the relationship comes to a sad end. Olivia finally comes to the realization that this relationship is contributing to her sadness and is asking for her partner to love her less, if loving her means her constantly being unhappy. It’s super devastating and achingly sad. This was a very painful cut from the top 10, but the absolute best songs in Olivia’s discography really made it a stiff competition. But for what actually made the top 10...

10. drivers license

This was a pop culture moment. I genuinely can’t wait for the day when my kids ask me “Hey dad, how did it feel when Olivia Rodrigo became a superstar overnight?” And yeah, I didn’t know who Olivia Rodrigo even was before “drivers license”—the only Disney shows I was watching were the ones widely regarded as classics like Phineas & Ferb and Jessie. But hey, “drivers license” would not have made Olivia such a huge popstar if it wasn’t an amazing song in its own right. It might not be as mature as her later work, but it wasn’t trying to be. It’s very intentionally high school, which adds weight to the word “forever” because yeah, when you’re in high school, that’s your entire world. It feels like everything that happens then is forever. “drivers license” is an incredible showing of Olivia’s vulnerable songwriting and the potential she had going forward. Yeah, this is still excellent 5 years later, and a promise of greatness that Olivia would only deliver in spades. I’m still salty that this was #1 on my 16th birthday and I didn’t get my drivers license that day though.

Now for the real cream of the crop...

 THE 10/10s - FANTASTIC/PERFECTION TIER

9. u + me = <3

Yeah, you can expect a ton of you seem pretty sad for a girl so in love in this top 10. I love the album so much and the best songs are truly special. “u + me = <3” is just pure infatuation in musical form, with the happy guitars and the upbeat tempo selling the vibe that “you plus me equals a heart forever”. What a banger!!

8. the cure

I will admit that if I did this ranking a few weeks ago, this would’ve fallen in the 9/10s. I initially thought the song took a bit too long to get going, but what won me over were two things: 1) how the song opens the “you seem pretty sad” side of the album in context and 2) the drum breakdown around the 3:30 mark, which makes the slow buildup throughout the first half of the song really pay off. This is the point in the album where the initial infatuation Olivia felt at the start of the relationship starts fading in turn for something sadder and it’s a fantastic song.

7. purple

This is the last song on the “girl so in love” side of the album, and probably the most transitional song on it—it serves as the subtle tipping point from the relationship making her happy into making her sad. It starts with a really terrific liquid drum and bass buildup that puts me a bit to mind of Justin Bieber’s “Ghost” (one of my all-time favorite songs) as Olivia talks about having a favorite florist and local grocery store and her no longer being a tourist. It implies that she’s settled down with this guy. She says she “sees the world in purple”, referring to feeling like she’s living out her dreams. But the real thing that makes this feel special is the outro, where it subtly flips from “melt with you ‘til it all turns black” to “melt with you ‘til it just feels sad”, signaling the turn from the “girl so in love” side to the “you seem pretty sad” side.

6. my way

Shoutout to when I was listening to you seem pretty sad for a girl so in love and got to this song my Spotify crashed haha. Anyways, what “my way” reminds me of most is the sort of flirty/trashy alternative girl rock songs that I could see coming out of Avril Lavigne in the 2000s. The song is about a girl crossing boundaries with Olivia’s boyfriend and Olivia calling out that shitty behavior. And while I was writing that previous sentence I kinda constructed this being the possible “other side” to Avril Lavigne’s “Girlfriend”. The production kicks ass too—the guitars call back to the 2000s punk scene perfectly. Yeah, what a fantastic banger.

5. cigarette smoke

The final track on the album, where the rebound energy of “expectations” gets stripped back for an immersive chamber pop cut that pulls the focus back to the now finished relationship central to the album. I love the callbacks to “begged” and “honeybee” in this song to serve as painful memories of the relationship. The relationship might’ve ended, but the memories of it linger, like cigarette smoke. Olivia says in the song that like cigarette smoke, the memories of the relationship cling to her clothes. She can really paint the full scene—an empty and quiet house with the shower still on, 5 beers in the fridge, and the 2nd car gone. It’s left ambiguous whether she ever moves on and finds that special someone or if the cycle begins anew, which is a huge part of its power. Like cigarette smoke, the emotional impact of this album will linger with you for a few hours after you sit through it—utterly fantastic song.

4. what’s wrong with me w/Robert Smith

This is Olivia’s first collaboration away from Disney. She’s gone on record to say that she loved working with and talking to Robert Smith of The Cure. And knowing she’s a music nerd, I can tell how much she loves The Cure’s music based on their chemistry in this song. It’s a hazier pop rock cut where the more details Olivia adds, the more sad it becomes. A point on the “you seem pretty sad” side where she knows rationally she should be happy—she’s got a partner who should make her feel complete and she went to the doctor and she said she was fine. But for some reason, she resorts to meditation with a bottle of wine and she can’t eat or sleep. It’s fantastic in every way...so what 3 songs could be better...?

3. maggots for brains

A fantastic new wave cut!! I adore the melodic guitars and it captures the initial feeling of the relationship where when your partner isn’t there with you, you’re a sad excuse of a person. More than anything though, this is just really fun.

2. drop dead

Surprise? Maybe? In my Chill Pick article, I definitely was cooler on this because to quote directly from what I said there, “I feel like Rodrigo is straying farther and farther away from the vulnerable songwriting that broke her through initially”. But “drop dead” is a song that only gets better with every listen for me. It’s super fun and euphoric as the opener to the album where Olivia meets the guy central to the relationship detailed in the album at a bar. She says if he kisses her she might drop dead and that she stalked him on the internet and always had a vision of them standing next to each other. Really, the only thing I would change is instead of “Pisces and a Gemini” on the bridge, it should’ve been “Pisces and an Aquarius”. Get it? Because obviously I’m the guy Olivia is singing about, you see because...okay I’ll leave now. But yeah, “drop dead” is fantastic, so what could be better?

Honestly, I don’t think it was gonna be anything else...

1. bad idea right?

“bad idea right?” has always been a banger from the very first listen and it’s only gotten better over the years. The attitude, the 90s rock production, the quotability, everything just wraps this up into the best song Olivia has ever dropped. The quotability is insane, from “the biggest lie I ever said” to “fuck it it’s fine” to “just tripped and fell into his bed”, paired with that killer self-aware attitude just make every second of this song absolutely wonderful. And that’s all in spite of the fact that the chorus is literally just Olivia repeating the same note over and over!! I really hope Olivia performs this live when I see her in December because I know for a fact that it’ll go off unbelievably hard. “Bad idea right?”: without question Olivia Rodrigo’s best song. Olivia, if you’re somehow reading this, you better perform this or I’ll be very let down—no pressure.

And we’re finally done!! My next article will be my Chill Pick article on Friday and after that should come my 1992 lists!! Stay tuned for that and until then, if you wanna list your favorite Olivia Rodrigo song(s), the comments are right there and I’d be eager to see where the consensus falls!! Or if you wanna put predictions for either of my 1992 lists, you can also put those in the comments!! Until the next article, remember to keep it Fire!