The Top 10 Worst Hit Songs of 1999

 

The Top 10 Worst Hit Songs of 1999

Hey guys, it’s Fire from Fire’s Flaming Hot Takes, and today we’re counting down the top 10 WORST hit songs of 1999!!

So 1999 seems to be generally agreed upon as one of the best years for pop music of the 90s. And honestly, I can see why, even if I think I’d give an edge to 1996 and, to a lesser extent, 1998. It was the end of not only the 90s, not only a century, but the end of a millennium. What this year’s pop music reminded me of most was 2021—a big and important year for pop music that might not be quite among the very best years of its respective decade, but one where the great iconic hits overshadow the worst stuff by a considerable margin. I’ll talk more about the great trends in 1999’s pop music in the best list, but in the meantime, the worst hits of this year can be mainly lumped into a generic category of tedious and cheesy ballads and/or songs that have aged really badly thanks to events that would come to light 20-30 years later.

The songs eligible for this list must have

• Debuted on the Hot 100 YE for 1999

• If the song is a repeat, it must have beat or matched its standing compared to the previous year

• Songs in the top 20 of the 1999 YE are eligible regardless of the first two rules

• No Hot 100 Airplay rules this time, this was the first year where Billboard allowed airplay songs to chart!

So you got all that? Let’s look at the dregs that probably came as a consequence of Y2K with our dishonorable mentions!!

DM #1: Jay-Z - Hard Knock Life (Ghetto Anthem) (YE: #89, PEAK: #15)

This song was one unfortunate choice away from being an admirable rags-to-riches story. And yeah, there’s no getting around it—that Annie sample sounds awful; it’s so stilted against the piano keys. In a world where “Mama Said” by Lukas Graham exists, I can’t say this is the worst song I’ve heard that samples “Hard Knock Life” from Annie, but this still sucks.

DM #2: Lonestar - Amazed (YE: #85, PEAK: #1)

I’m a bit shocked how much I disliked this when I listened to it. I did imply years ago when I wrote my worst list for 2000 that it was bad and probably would’ve made that list had it not been a repeat, but I was still taken aback by how awful I genuinely thought this was. The fundamental flaw with this song is that it’s an oversold, generic, and cheesy ballad. It’s not even that I think these types of country ballads are bad on principle—“Colder Weather” by the Zac Brown Band is one of the best country songs I’ve ever heard. But what made “Colder Weather” work is that it had a truly heart-wrenching story and beautiful vocals from Zac Brown that justified having such a big arrangement. With “Amazed”, frontman Richie McDonald is the definition of whitebread blandness—he does not sound sincere here, he sounds like he recorded this for a generic proposal song anyone could play but with no heart. The song has the single most overused topic in all of pop music: “I heart you”. And complete with the cheesy as hell guitar solos, this is a tedious bore that naturally, was the first country song of the 2000s millennium to hit #1 on the Hot 100. Great job America. I’m not remotely amazed by this, if you can’t tell!!

DM #3: 98 Degrees - I Do (Cherish You) (YE: #68, PEAK: #13)

What was the point of 98 Degrees being a thing in the 90s? They don’t make themselves distinct in any way and when you had boybands like the Backstreet Boys and *NSYNC, we already had the boyband market covered. Nick Lachey and the other guys (who even cares about what their names are?) have no charisma here. I don’t hear love for a partner, I hear a cliche song that everyone here knows is cliche, but they still want to make money, so they put in the effort of a 5th grader presenting a science project they didn’t have much interest in doing. I mean, they certainly pull out all the stops to get an A on their “write a love song” assignment—weak as hell key change, dull instrumentation, and even a false sense of buildup with effects that don’t stick out in any way. If you're asking whether I love this song this much...I do...not. In any capacity.

DM #4: 98 Degrees - Because Of You (YE: #69, PEAK: #3)

Yup, more 98 Degrees!! I honestly didn’t hate this when I was making my lists for 1998 (I still thought it was mid though), but when relistening to it for this list, I was really struck by the sheer lack of flavor anywhere, from the passionless vocals to the generic acoustic guitar instrumentation. Genuinely, who could like this? This doesn’t sound like someone grieving from a breakup and begging their ex to come back, if anything, this isn’t “not over it” enough! Ne-Yo and Kelly Clarkson outsold, next!!

DM #5: Jesse Powell - You (YE: #59, PEAK: #10)

I don’t really have much to say about this song other than it wastes some rather impressive vocals from Jesse Powell with those awful backing vocals and a weak falsetto. Something about the “the way you walk, the way you talk…”’s just drives me up the wall, and I don’t know what it is. Though I can certainly put some blame on the production, with that thudding percussion just trudging through the song, which doesn’t help the instrumentation convey any sort of mood. RIP Jesse Powell, but this song still sucks.

DM #6: Sugar Ray - Every Morning (YE: #8, PEAK: #3)

Like “Fly” did in my 1998 worst list, “Every Morning” makes the list for 1999 because the vocals sound awful. The amateur vibes that radiate from this song aren’t inherently a weakness—something that Smash Mouth pulled off really well in “All Star” as you’ll see in my best list—but when the amateur vibes don’t come with any charm, it becomes insufferable. It sounds like the worst elements of a yacht rock song played on a talk box!!

DM #7: Sarah McLachlan - I Will Remember You (YE: #70, PEAK: #14)

How does this sound like more of a PETA commercial than the literal Sarah McLachlan ASPCA song that was a hit in 1999? Say what you will about “Angel”, at least the lyrics were uniquely sad and sincere!! “I Will Remember You” has nothing going for it, it’s such a borefest. McLachlan doesn’t even sound all that hurt or devastated, it’s just so basic that you can put this as the soundtrack to any video about a kid or animal growing up and it wouldn’t enhance the video or detract from it, it’s the musical equivalent of a window, it’s there for decoration but it doesn’t actually do anything to help the thing it’s used in. “Angel” is genuinely good, stop memeing that song to death and instead meme this one, far less will have been lost.

DM #8: Ricky Martin - She’s All I Ever Had (YE: #52, PEAK: #2)

Ricky Martin- I mean Ricky Main (if you get what I’m referencing then hello Pulse users) was one of the artists who burst onto the scene in the wake of the Latin Music explosion. And given how much of a banger “Livin’ La Vida Loca” is (stay tuned for my best list), it’s stunning how much he sold out literally one single later!! This is no different from any of the other generic AC love ballads of the time. You can’t make out any individual instruments from how bland the song is and it just sounds so cliche. Any traces of the Latin Music explosion are completely sanded off, it’s so colorless. Be real for a sec, even if the Latin Music explosion never happened, this probably would’ve still been a hit because this is the sort of safe glop that the radio eats up.

DM #9: Len - Steal My Sunshine (YE: #78, PEAK: #9)

...aaaaaaaaaand here comes the backlash. Look, I used to hate this song way more, probably because the quality of its sound was so much worse on the radio than my headphones. But I’m sorry, I still dislike this song. The production sounds seasick, Marc Costanzo’s vocals sound terrible, and Sharon Costanzo’s vocals don’t feel summery so much as punched in during mastering. The most summery vibes I get from this song are the feeling of getting sunburnt so badly on the beach that every square inch of your body is in unbearable pain. The one concession I’m making is that it missed the list proper. Even then I was being generous. If I did this list a few years ago this likely would’ve made my top 5. Count yourselves lucky.

DM #10: R. Kelly & Celine Dion - I’m Your Angel (YE: #16, PEAK: #1)

The queen of cliche soccer mom ballads duets with the king of peeing on children for one of the dullest songs I’ve ever heard. It should be no surprise that R. Kelly’s voice is innately repulsive to me because of his crimes. He has no chemistry with Celine Dion, which does not help things when the instrumentation is so bland and cliche! This song is not my angel, and certainly neither is R Kelly.

Alright, now onto the list proper!!

10...So when you have covers of songs, a fair assumption is that the cover is at least one of two things: A) a faithful cover that’s more or less just a straight copy where the singer is clearly expressing love for the original article in how they sing it, or B) the cover takes a different sonic direction than the original that still keeps what made the original work special. We’ve seen awful covers of great songs in the past—Ritt Momney covering Corrine Bailey Rae’s “Put Your Records On” or especially Calum Scott’s infamous take on Robyn’s “Dancing On My Own”. But what happens when someone tries to cover a song that already sucked and then somehow does it worse?....

10. Mark Chesnutt - I Don’t Want To Miss A Thing (YE: #67, PEAK: #17)

I already don’t like Aerosmith’s original song for how unbearably cheesy it is, but God, at least Aerosmith knew how to put power into “I Don’t Want To Miss A Thing”!! Mark Chesnutt is trying to take the song in a different sonic direction—country—and yet while it’s concerning that we’re at the point where a country song is indistinguishable from a glam rock song, this cover is also just a billion times worse because none of the instruments land with any sort of intensity, especially that guitar solo, which just sounds stripped of all the potential heart that Aerosmith’s original had. I also don’t get any sincerity from Mark Chesnutt here, he sounds like he’s just singing it at karaoke on a dare from his friends. Say what you will about Aerosmith, you could believe that they miss you and they don’t want to miss a thing. You can skip this, you’re not gonna miss a thing.

9...So arguably one of the most frowned upon things in songwriting is when you compare sex to food. More often than not your metaphor becomes muddled and the song becomes gross. Notable examples include “Bon Appetit” by Katy Perry or “Yummy” by Justin Bieber. Given how those are fairly recent songs, you’d think that this songwriting concept was executed well in the past. And my answer to that would be...no, I just don’t think anyone bothered to point it out. Case in point...

9. Dru Hill - These Are The Times (YE: #66, PEAK: #21)

At first I had this as a dishonorable mention, but literally as I was about to write this entry, I noticed how...borderline cannibalistic the lyrics are. Like, from “tear you up in little pieces” to “swallow you like Reese’s pieces” to “morning, noon, and supper time”, this is just creepy. Aside from ruining my favorite chocolate, all the food imagery makes this feel less like a sex jam and more like the guys in Dru Hill are literally about to eat the girl—it’s off. These are the times I wish Reese’s could file a defamation lawsuit because I feel like this song caused their stock to plummet by 30%.

8...So in the early 2010s, One Direction’s music was blasted for their lyrics feeling questionably condescending and predatory to young and insecure girls. Personally, I never was really on that bandwagon. Outside of “Little Things”, I always felt the songs came from a sincere place and the clumsiness could be credibly defended with “they were young, they didn’t know what they were doing”. Besides, at least One Direction was having fun, compare that to this...

8. Joey McIntyre - Stay The Same (YE: #92, PEAK: #10)

On the surface, this seems like just another interchangeable boring AC ballad that was all too common throughout the 90s. But dig a little deeper and it starts feeling questionable. This feels like it was weapons-tested for Joey McIntyre to appeal to any young girl’s insecurities with lines like “Don’t you ever wish you were someone else?” or “You were meant to be the way you are exactly”. McIntyre includes no specific details about the girl he’s singing about. He just knows that whatever insecurities you have, young girl, just love yourself! HE thinks you could be whoever you want to be! Open up your heart and let it show you the way, into his pants from the way it sounds. The song also just ticks all the boxes on the boring AC ballads checklist—cheesy key change, bland as hell instrumentation where individual instruments are just pureed into mush, and vocal delivery that does just enough to make you think McIntyre is saying he believes in you but not quite enough to make you feel like he actually believes it. At least One Direction knew how to write monstrous hooks, the hook here is so generic that I literally can’t tell what part is supposed to be the chorus if I don’t have a lyrics sheet in front of me! I’m glad musical trends didn’t stay the same for the next ~30 years so we don’t get terrible goop like this anymore!

7...Prior to the 2000s, there were plenty of instances of two versions of the same song being on the YE list instead of it being credited to one song. I think it has something to do with how the singles were issued, maybe in how the remixes were stylistically, maybe even both. This was one of those cases, too bad the remix is terrible!....

7. Alabama f/*NSYNC - (God Must Have Spent) A Little More Time On You (YE: #100, PEAK: #29)

This is just a true bore. For being a country remix, it sounds completely indistinguishable from the original song!! John Alabama’s twang is the only thing about this remix that is even vaguely country!! And literally while I was writing that previous sentence, I read that this was a remix that Alabama only recorded because their popularity was declining and this was just an attempt to stay relevant! So we have confirmation that this was a transparent cash grab and nothing more!! The original song is already ass as it is, we didn’t need this. And you know what, on that note...

6...Prior to the 2000s, there were plenty of instances of two versions of the same song being on the YE list instead of it being credited to one song. I think it has something to do with how the singles were issued, maybe in how the remixes were stylistically, maybe even both. This was one of those cases-okay you know what the setup is here already...

6. *NSYNC - (God Must Have Spent) A Little More Time on You (YE: #45, PEAK: #8)

You know what, for as equally terrible as the Alabama remix of this was, at least the twang, if nothing else, made it the tiniest bit unique!! *NSYNC’s original song is a sleepy and boring love ballad that might sound sincere, but not really distinct in any way, it’s dreadfully boring and unstimulating. I get why someone might like this—after all, *NSYNC are quite sincere here. But for me, this is just too boring for words. If anything, God must’ve spent a little more time on making this an extreme borefest.

5...So in 2010, Train released “Hey Soul Sister”, and almost instantly, people were in shock and horror by how imbecilic it was, a 10 car pileup of disconnected and wack lyrics that didn’t even try to make sense. The song was (and still is, really) a staple on worst lists for that year. Now me? I never hated “Hey Soul Sister”, in fact I used to love it, it made my best list for that year when I wrote it in 2021!! And while I admittedly don’t really stand by that take, I still like it because the delivery felt earnest enough to the point where the blissful idiocy was charming to me. But what happens when you take the same idiocy and 10 car pileup of disconnected lyrics but make it not charming?...

5. LFO - Summer Girls (YE: #38, PEAK: #3)

Say what you will about Pat Monahan of Train and his knack for horrendous lyrics, at least he never RAPPED!! And I genuinely don’t know what the point of this song is. It starts with a tossed-off reference to New Kids On The Block, and then goes into a tangent about how Chinese food makes him sick? It gives word salad, but not in a way that still conveys a coherent vibe. At least “Astronaut In The Ocean” by Masked Wolf’s word salad lyrics still conveyed a mood of sounding like hype!! At least Hot Chelle Rae’s “Tonight Tonight” was trying to be an upbeat party anthem!! But I genuinely don’t know what context you’re supposed to listen to “Summer Girls” in, is it supposed to be hangout music? If so then it utterly fails because the rapping is so painfully white. Is it supposed to be hype? It also fails at that, the production is way too laid back to sound like a hype anthem! I will concede that the hook is annoyingly catchy, but all that does is just reinforce how meaningless the entire song is. New Kids On The Block had a bunch of hits and “Summer Girls” by LFO makes me sick, next!

4...So in the TikTok era, aka the era of remix gaming to chase #1’s on the Hot 100, there have been plenty of cases of remixes of a song where it all feels graceless. It’s clear that it was only done for the paycheck and/or the #1. The biggest example I can think of off the top of my head is the Ariana Grande remix of “Die For You” in 2023, where it sounded like they just shoved Ariana onto the parts where there were no vocals to make for an utter mess. This next song was not a remix, but the comparison to that “Die For You” remix was honestly the closest comparison I could think of to describe how it sounds...

4. *NSYNC & Gloria Estefan - Music of My Heart (YE: #97, PEAK: #2)

I mean, “Music Of My Heart” is obviously a snooze, but what makes this stick out from all the other sleepy ballads on this list is the negative chemistry Gloria Estefan and *NSYNC have. I’ll be blunt: this sounds like *NSYNC just badly adlibbed over a solo Gloria Estefan track. The bassline sounds like garbage, it’s so leaden and weighs down any grace the song could have. Yeah, that’s about it. If this shit is the music of your heart...you can keep it, no girl who loves this can give me her heart (watch my future girlfriend will consider this an all-time favorite and this review will age like shit). This is still terrible though.

3...Usually a song sounding ahead of its time is a compliment. Not here though!!...

3. 98 Degrees - The Hardest Thing (YE: #37, PEAK: #5)

This song was truly ahead of its time in being terrible. I could mention how once again Nick Lachey and the other guys who no one gives a fuck about have no charisma, but the main complaint I have are those random synth stabs in the mix that sound like they were found in a dumpster in 2008!! That was what I meant by this sounding ahead of its time in being terrible!! The synth stabs are jarring and don’t work for what’s supposed to be a raw confession of love-wait actually...this isn’t a love song? Yeah, this is a breakup song after this guy cheated on his girlfriend and he has to do the hardest thing possible and break up with his girlfriend and say he doesn’t love her and that he was sleeping with someone else and that he’ll have to show no emotion when she starts crying? BULLSHIT. BULL FUCKING SHIT. You don’t even show any emotion in this song!! I don’t buy that not showing emotion when she starts crying after you break the news that you were unfaithful is the hardest part of it all!! It wasn’t even hard enough for you to NOT cheat on your girl!! This song proves that 98 Degrees offered little of value to music in the 90s outside of being easy worst list filler. Next!

2...I feel like for me, certain vocal delivery and even slightly questionable lyrics trigger my fight or flight response because my brain just defaults to the song being about a sexual predator. See my 2001 worst list where “Follow Me” by Uncle Kracker topped the list because of that triggering response I had. This was a similar case, and while I’m now 4 years older than I was when I wrote that 2001 worst list and can now more easily be realistic about that specific combo of vocals and lyrics, yeah, this song did actually trigger that response for me...

2. Shawn Mullins - Lullaby (YE: #46, PEAK: #7)

When I saw this song was called “Lullaby”, I assumed the obvious joke would be “I hate when artists write my jokes in their song titles for me”. Then I actually listened to this song and...I can’t be the only one getting skeevy vibes here, right? The way Shawn Mullins talks about this young girl sounds like he’s drooling over her and the ambiguity over how old the girl in question is in the song makes my brain default to the worst possible option. It certainly doesn’t help that Mullins is a really awful singer—he’s straining to hit mid-range notes and as a whole it’s just miserable to listen to. Maybe the vibes I get aren't a valid reason for this to nearly top this list, I don’t know. What I do know is that this song is fucking trash. If only this was a lullaby. So what’s worse?

Well, before we get to that, there’s one IDM I need to talk about...

IDM #1: Sporty Thievz - No Pigeons (YE: N/A, PEAK: #12)

So when I write my year-end lists, I try not to watch any other lists on YouTube until I finish writing the article because I don’t want my opinions to get influenced. However, I finished this article and was about ready to publish it. Then I decided to watch Lyzette G’s worst list for 1999—I figured the article was already written and my opinions wouldn’t really be swayed all that much. This song was at the very top of their list. I gave it a listen and...holy shit, this might genuinely be the worst response song I’ve ever heard. This song is clearly intended to be a response to TLC’s “No Scrubs”; this song has the same beat, same lyrical structure, everything. They even make a reference to the girl in the song calling them a scrub multiple times!! And this song just takes a turn for the horrifically misogynistic. They go on and on about how this girl is a flat-assed pigeon who everyone laughs at and it’s not funny. The way they even try to replicate the sung bridge is just abysmal. If this is supposed to be a parody, what’s the joke? Yeah, it shouldn’t be a shock that if this was eligible it would’ve topped this list and it wouldn’t have been particularly close. As for what actually did top the list...

 

1...Honestly as soon as I saw there was a hit song in 1999 that had these two collabing, I think I knew in my gut that it belonged at the top of this list...

1. Puff Daddy f/R. Kelly - Satisfy You (YE: #95, PEAK: #2)

It should go without saying that R Kelly and Diddy making a song together is gonna look a certain way in 2026. It forces me to read every single lyric in this song from the perspective of a pedophile talking about his actions. Here are just a few awful lyrics in this song along with brief commentary on them to show you just how this reads to me:

“No, he'll never make love to you like I do

So give it to me

'Cause I can show you 'bout a real love”

Yes, R Kelly the 14-year-old girl you peed on's boyfriend probably wouldn’t pee on her too. I can’t imagine any sane person considering that a way of making or showing real love.

“We one in the same girl, it ain't a game

So I can't play with you, I wanna lay with you

Stay with you, pray with you, grow old and gray with you”

Why can’t you grow old and gray with this person, Diddy? Maybe because the youngest Diddy party victim was allegedly only NINE YEARS OLD???? When you were in your LATE TWENTIES TO EARLY FORTIES??????????? And then the moaning that likely sounds like one of their victims comes in and that sealed the deal for me. Whether it was by accident or by design, to me “Satisfy You” by Puff Daddy and R Kelly is pure self-incrimination of two pedophiles who were able to get away with their crimes for 20+ years. It’s a scathing indictment of just how much we let shitty people get away with the heinous crimes they commit and regardless of whether you believe in “separating the art from the artist” as a blanket practice for every artist, it should at least be common belief that we hold these monsters accountable for their actions. The real question is whether we’ve really gotten better now. “Satisfy You” by Puff Daddy featuring R Kelly, by far the WORST hit song of 1999. Fuck both these artists so hard.

And that’s the worst list done!! My next article should be, if not my monthly Chill Pick article, the best list for this year, stay tuned for that and until then, if you have predictions for that list or your own lists of the worst hit songs of 1999, please comment them below!! I’m eager to read them. And until the next list, the Spotify playlist with every song on this list is linked right here. And until the next list, remember to keep it Fire!