The Top 10 Best Hit Songs of 1999

 

The Top 10 Best Hit Songs of 1999

Hey guys, Fire here, and it’s that time again—today we’re counting down the top 10 BEST hit songs of 1999!!

So as I said in my worst list, 1999 seems to be generally agreed upon as one of the best years of the 90s for pop music. And I tend to agree, it was an iconic year for mainstream music where the boyband wars were at their apex, with *NSYNC and the Backstreet Boys (and their fanbases) duking it out to see who was the biggest boyband. Additionally, this year also saw the dominance of TRL, meaning that teen pop from artists like Britney Spears and Christina Aguilera had a strong showing. This was also the year of the Latin Music explosion, meaning acts like Ricky Martin, Lou Bega, and Marc Anthony were seeing success. 1999 was arguably the year where the most iconic 90s hits have lasted—I still hear a good chunk of these songs as radio recurrents. But one of the most notable things in my eyes is that 1999 was the first year that airplay singles were allowed to chart on the Hot 100 (meaning they didn’t need a physical release), meaning that country music, which was in a golden age in the 90s was notching consistent crossover success on the Hot 100.

This all led to a year that I would absolutely call very good, though I would hesitate to say this year is better than 1996 or 98. Like I said in my worst list, the great iconic hits overshadow the worst shit by a large margin. And while I was more skeeved out by most of the worst hits of the year, I had a ton of fun with the best hits this year!!

The songs eligible for this list had to meet one of these three criteria:

• They debuted on the Hot 100 YE for 1999

• If they are repeats, they had to beat or match their standings compared to the previous year

• Any songs in the YE top 20 for 1999 are eligible regardless of the previous 2 rules

You got all that? Great, now let’s look at the great and iconic hits that people were listening to as they celebrated surviving Y2K with our honorable mentions!!

HM #1: Monica  - Angel Of Mine (YE: #3, PEAK: #1)

So given that love ballads were very plentiful throughout the 90s, most of the time they’re boringly cliche and generic. But if you’re gonna go down this route, “Angel Of Mine” by Monica is a pretty great example of how you do it well. The R&B production is gentle and intimate with the more Latin-inspired(?) guitars, Monica sounds really sincere in her profession of love for her partner, and she sells it so well that the cliches in the song don’t feel cliche! Cute little song!

HM #2: Lauryn Hill - Doo Wop (That Thing) (YE: #41, PEAK: #1)

Yeah, not much to say here other than that Lauryn Hill is incredibly skilled as a rapper and singer, delivering an absolute banger where the neo-soul/boom bap vibe just coalesces effortlessly. Great song!! But while we’re talking about Lauryn Hill...

HM #3: Lauryn Hill - Ex-Factor (YE: #62, PEAK: #21)

While “Doo Wop (That Thing)” is just a straight up bars-fest, “Ex-Factor” shows how skilled Lauryn Hill is as a singer. Her vocals are beautiful and her raspy tone has a very distinct texture that makes the song feel uniquely like hers. I also just think that guitar solo kicks so much ass. It’s a great neo-soul song that is so iconic that it makes all the sense in the world why Drake sampled it in 2018 for “Nice For What”.

HM #4: Whitney Houston f/Faith Evans & Kelly Price - Heartbreak Hotel (YE: #4, PEAK: #2)

Whitney Houston is nowadays remembered for her belting ballads like “I Will Always Love You” (which is good, don’t get me wrong) but a part of me wishes that her R&B cuts were better remembered. And “Heartbreak Hotel” is a great display of how well she fits on an R&B track. Lyrically, “Heartbreak Hotel” is about the narrator discovering her partner was unfaithful and Whitney Houston, Faith Evans, and Kelly Price all sell the betrayal so well. They aren’t angered or seeking revenge—they’re just...heartbroken. It’s not overselling the heartbreak, it’s more achingly sad. It’s a shame that these three had to stay at the heartbreak hotel, but they made a pretty great track out of it.

HM #5: Faith Evans - Love Like This (YE: #58, PEAK: #7)

While Faith Evans felt a bit overshadowed on “Heartbreak Hotel”, she absolutely proves how great she is as a performer on “Love Like This”. It’s a more upbeat disco-leaning track that doesn’t really sound all that different from something Mariah Carey would’ve made around this time. The lush and upbeat production matches the lyrics, which are just pure lovestruck bliss that Faith Evans sells in her exuberant delivery. Yeah, this is a pretty cute track!!

HM #6: Tal Bachman - She’s So High (YE: #51, PEAK: #14)

Well, this shouldn’t be much of a surprise if you’ve read any of my other best lists I’ve done for the 90s. I really like this brand of power pop with big hooks, and this hits all the sweet spots for me. What Tal Bachman kinda lacks in his vocal talent (his falsetto and raspy voice are admittedly not fantastic lol), he more than makes up for in his gritty attitude that still oozes charm. The narrator is also just head over heels in love with this girl who Bachman makes abundantly clear he is way out of her league and I just can’t help but find it charming. It’s “Cooler Than Me” by Mike Posner if it was actually good, it’s not from a place of jealousy, but one of admiration. Great stuff!! But speaking of lovestruck power pop...

HM #7: Goo Goo Dolls - Slide (YE: #13, PEAK: #8)

This is just a great little jangle pop song with its tight guitar-driven groove and great vocals from Johnny Rzeznik. The happy sounding production obscures the fact that this song is actually about a couple questioning whether they should get an abortion, get married, or break up (I literally only found this out while writing this review!). And what makes this work is that the happy production accentuates Rzeznik’s commitment to supporting whatever decision his partner takes rather than clashing with the dilemma at the center of the song. A line like “What you feel is what you are/And what you are is beautiful” is just so charmingly sincere. It certainly helps that they hit on an incredibly strong melody. Great track!!

HM #8: Santana f/Rob Thomas - Smooth (YE: #19, PEAK: #1)

This song has only grown on me over the years. Santana’s guitar work is absolutely a bit dated, but damn if it doesn’t still have a swing to it. And Rob Thomas’s raspy voice serves as a perfect complement to the production. Not much else to say here, it’s iconic and a song that reliably still gets strong recurrent airplay today for a reason!!

HM #9: Goo Goo Dolls - Iris (YE: #94, PEAK: #9)

I already covered this in my 1998 best list but to keep it short, it’s a beautifully arranged song that perhaps could’ve used a bit more punch in that chorus, but still remains elegant as ever thanks to strong guitar work. As I said in that list, “I think you know why ‘Iris’ by the Goo Goo Dolls is a fucking great song.”

HM #10: Shania Twain - That Don’t Impress Me Much (YE: #32, PEAK: #7)

This was gonna make the list proper for the longest time. That melody is so strong as Shania Twain just sells her sass at this guy who’s trying to put on a pose of strong masculinity to win her over. The key lyric here is “But that won't keep me warm in the middle of the night”. Twain isn’t looking for some strong man who will come to her rescue if she’s a damsel in distress, she just wants a genuine, intimate connection. You could have the moves and a car or be a rocket scientist, Brad Pitt, and Elvis, but that doesn’t mean a thing if you don’t have a genuine connection with her. This is a great song that you can honestly consider the honorary #11 on this list.

Alright, now for the list proper!

10…For a song to be the #1 biggest song of the year, I feel like it should represent something. It’s the song that when music historians start analyzing the popular music of a year, it will be what tells them “this is what captured the pop music zeitgeist this year” or “this represented the biggest trends in music, art, and culture this year”. Admittedly, with the increased decentralization of pop music thanks to the rise of streaming in the late 2010s, it’s harder to see the YE #1 as having these qualities. However, I can’t deny that this song being the biggest song of 1999 is kinda huge....

10. Cher - Believe (YE: #1, PEAK: #1)

Besides being the widely cited pioneer of using autotune to distort a voice in unique ways, “Believe” being the biggest song of 1999 and being widely adopted as an LGBTQ anthem signals to future music historians that this was the point we started recognizing LGBTQ people as a marginalized group. It’s a bookmark of a time we started becoming more accepting. That’s all obviously incredible, but the song itself is also great—it’s an upbeat and forceful diva house cut all about getting over a breakup. This song is poptimism in its truest essence—a symbol of wide acceptance with a huge hook that the gays love (that’s a qualifier nowadays for a song to be a poptimist anthem right lol). Even as I think the autotune effects distort Cher’s voice a tad too much (hence why it’s only #10 here), this is a pillar of hope and acceptance that marked a powerful step forward in society as we entered a new millennium.

9...It’s impossible to talk about great pop music of any year of the 90s without talking about Mariah Carey. A truly gifted singer with a huge vocal range, she was able to straddle the line between belting out whistle notes and soft and gentle cooing effortlessly. It was her who arguably paved the way for artists like Ariana Grande to be A-listers today. I think you’ve figured out by now that the next song is a Mariah Carey song, and while I wouldn’t call it one of my favorites from her, she absolutely had a formula that worked...

9. Mariah Carey f/Jay-Z - Heartbreaker (YE: #35, PEAK: #1)

“Heartbreaker” isn’t my favorite Mariah Carey song by any means since it does kinda feel like Mariah sticking to a bassline formula, but come on, that bassline formula is still fucking great. The synth funk production is super lush and bright—it radiates endless joy. Mariah genuinely sounds like she loves being there, the pure love she has for singing shines through and it makes the song feel all the more blissful. And Jay-Z serves as the perfect hypeman, his flow just seamlessly gels with the production. Yeah, not much else to say, this is a pretty great song.

8...So I think 2014 is widely remembered as the year of the ass, mostly for the worse, because most, if not all of the ass anthems that year were pretty awful. From “Wiggle” by Jason Derulo to “All About That Bass” by Meghan Trainor, there were so many garbage ass anthems that suggested that the artists didn’t know how to do them right. This is kinda shocking because this was a hit 15 years prior that could’ve shown how ass anthems could be legit great!...

8. Juvenile f/Mannie Fresh & Lil Wayne - Back That Thang Up (YE: #75, PEAK: #19)

Juvenile, Mannie Fresh, and Lil Wayne are all on their A-game here. The beat from Mannie Fresh goes unbelievably hard, it strikes a great balance of being dark yet also lively. What makes this work in comparison to a lot of ass anthems is that the energy is high in every way with a great hook. This song makes me wanna go to the strip club and twerk. What a banger!!

7...Well speaking of high-energy bangers, let’s talk about arguably one of the most iconic songs from the late 90s Latin Music explosion...

7. Ricky Martin - Livin’ la Vida Loca (YE: #10, PEAK: #1)

First off, I don’t care, this image is objectively hilarious:

Anyways, “Livin’ La Vida Loca” is an absolute banger that holds up so well. Ricky Main is such a lively presence on this song and he really enhances the upbeat and manic fun of the song. The song is about a wild and fun chick living a crazy life. And the production absolutely matches that crazy energy with that surf rock progression, the salsa horns, and the ska guitar solos. It’s a ridiculously fun banger that’s held up remarkably well all these years later. Maybe I should stop staying locked in my house and running my blog and start living la vida loca. Yeah, you know what, it was a great run y’all, but I’m officially retiring (/j).

6...So in late 2016, MGK and Camila Cabello released “Bad Things”, which was pretty much universally panned by YouTube music critics for desecrating its sample with a seemingly complete and total lack of chemistry between MGK and Cabello. It was a staple on worst lists for 2016 and 17. Now me? That wasn’t the case, “Bad Things” actually made my 2017 best list and I still stand by that take. I have my pretty pretentious reasons for why I still love the song, but there’s no denying that the original source material is still better...

6. Fastball  - Out Of My Head (YE: #88, PEAK: #20)

Yeah, as much as I love “Bad Things”, “Out Of My Head” is obviously way better. The song’s sound kinda highlights why MGK and Cabello chose to sample the song. It’s a really timeless alternative rock song with an instrumentation that just sounds so lovestruck with really sweet drum work and guitar work that sounds lovestruck without sounding cheesy. It helps the song feel like a slow burn. No, “Bad Things” is not better than this, but if anything, I think there’s a place for both songs. If “Out Of My Head” was sung from the perspective of a serious and intimate relationship, “Bad Things” is from the opposite perspective—a toxic teenage fling that the two partners are convinced is much deeper than it actually is. Crucially, both songs preserve the joy of their respective experiences, which is what makes them work so well. Yeah, “Out Of My Head” is an amazing little song and so is “Bad Things”, I’m saying it.

5...But speaking of lovestruck alternative rock...

5. Sixpence None the Richer - Kiss Me (YE: #6, PEAK: #2)

I’ve loved “Kiss Me” from the first time I heard it, it’s just so sweet and romantic. Leigh Nash’s vocals feel so intimate and the little details she adds, like wanting her partner to kiss her under the milky twilight, on the moonlit floor, making the fireflies dance, by the broken tree house, and swinging her on the hanging tire, they all just make her feel like she’s directly talking to you. When I listen to this, I hear the girl I love (if she actually existed lol) begging for an intimate moment with me, it’s just so innocently youthful and lovestruck. It’s an amazing little song and if someone sang this to me, I think I’d be won over.

4...I put “Every Morning” by Sugar Ray on my worst list for sounding amateurish without any charm. Amateurish vibes don’t inherently ruin a song for me and there’s a way to make the amateurish vibes a strength of the song. Case in point...

4. Smash Mouth - All Star (YE: #17, PEAK: #4)

Maybe I have Shrek nostalgia here haha. But regardless, I think “All Star” is an excellent song. The guitars, the vocals, and lyrics like “The water’s gettin’ warm so you might as well swim” just scream amateur hour. But what makes this work is that Smash Mouth strike a great balance of sounding amateurish while not letting it compromise simply rock-solid composition and they clearly know how amateurish the song feels and they lean into it. That’s what makes this feel charming. There are also hooks crammed into every nook and cranny of the song, from the chorus to even the pre-chorus or the iconic first verse and “the years start comin’ and they don’t stop comin’”. Yeah, this is excellent and rightly is still remembered today.

3..So the Goo Goo Dolls are probably the 90s legacy act who’ve endured the most to me. I still hear “Iris” on my Hot AC station regularly and they still chart new songs on that format today. And we’ve already seen “Iris” on this list. But this is a song I don’t really hear get any recurrent airplay. It’s kinda been forgotten at this point. I at least still see “Name” get talked about, not this, though. Which is a shame because this might just be their best song to date...

3. Goo Goo Dolls - Black Balloon (YE: #64, PEAK: #16)

“Black Balloon” is just an amazing little song, it pivots from the more tight guitar driven groove that characterized “Slide” and the gorgeously big arrangement that characterized “Iris” in favor of a gentler acoustic guitar-driven jangle pop song that wrings out the more achingly sad lyrics effectively. The guitars give a really strong melody. And that underscores the lyrics, which detail the narrator’s lover suffering from heroin addiction and the narrator desperately trying to save her. Johnny Rzeznik captures the desperation of trying to save someone you love from their own self-destruction perfectly. Rzeznik’s commitment to sticking by his lover even if it gets worse for her and that there’s no time left for losing when she’s getting close to the edge really makes this land with a gut punch. And then the final chorus is where you realize that the lover in question has actually...passed away. I could possibly make the case for this song being what laid the groundwork for emo band Spanish Love Songs to record their masterpiece Brave Faces Everyone in 2020. It’s an incredible little song that really deserves to be better remembered today. So what two songs beat this?

2..But on the topic of earnest desperation to help someone in crisis...

2. Third Eye Blind - Jumper (YE: #40, PEAK: #5)

I already talked about “Jumper” in my 1998 best list and I still stand by what I said—it’s an earnest plea to a kid on the edge to stay alive, which frontman Stephan Jenkins sells so well. But the standout lyric to me is this:

“Everyone's got to face down the demons

Maybe today, you could put the past away”

When looking at what Jenkins said about the song, apparently he was aiming to have the song convey more than just one kid about to take their own life. He was aiming to convey a sense of understanding. Because everybody’s got their own demons. But maybe if we try living our life and not let our past consume us, we could put the past away and start being happy. It’s a powerful reminder to keep moving forward and coupled with those incredible guitar solos, “Jumper” is an excellent song—very nearly my favorite hit of 1999, except for one song...what could beat this?

1...When it comes to pop music in 1999, what is literally the first thing you think of? Not like “Y2K” or anything, just like what music trends do you think of? You might say the boyband wars, teen pop, TRL, or even the Latin Music explosion. What if I told you that there was a hit song in 1999 that in some way or the other embodies every one of these trends? A song that reliably still gets recurrent play and is a cultural staple to this day? Now that sounds like a classic song that you’d have no choice but to call the best hit of the year. But really, was there ever gonna be any other option for #1 on this list outside of my fire, the one desire?...

1. Backstreet Boys - I Want It That Way (YE: #15, PEAK: #6)

“I Want It That Way” was a song I’ve always loved, but it wasn’t until my first ever Boy Scouts camping trip back in 2017 where I truly saw how much of a cultural classic it was, even if I was too young to realize it at the time. At that campout, all day there was a group of older boys in my troop shouting the lyrics. And that, looking back, was solidification that “I Want It That Way” is a song that has lasted into Gen Z and likely for future generations to come. It’s a masterpiece of a song that really takes every big trend of 1999 and rolls it up into one utterly glorious pop song. It captures the boyband wars and how the Backstreet Boys are way better (/hj, *NSYNC have great songs too I swear lol), the boybands were one of the faces of TRL and teen pop in the 90s. It even kinda captures the spirit of the Latin Music explosion. That Latin Music explosion was all about fun and, in a sense, innocence. “I Want It That Way” is just so innocent in its zen-like incomprehensibility and the lines are all so memorable and fun to sing along to. I know I complained about the incomprehensible lyrics in my worst list with LFO’s “Summer Girls”, but while that song was painfully clunky and trying way too hard, “I Want It That Way” just rests in its zen and lets its vibe do all the work. In other words, “I Want It That Way” by the Backstreet Boys, without question the BEST hit song of 1999, and I wouldn’t want it any other way. Please to all future generations, don’t let this song die out, let its incomprehensible zen endure for the rest of time.

And that’s my lists for 1999 all finished! Next article will be my Chill Pick article (unless it’s already up by the time I publish this), but after that, I’ll be starting a 90s dive!! Stay tuned for that and until then, if you guys have got your own lists for the best hit songs of 1999, feel free to comment them down below!! Until my next article, Spotify playlist for this list is right here and remember to keep it Fire!!