Worst Songs List

Top 10 List: Worst Songs of 1999

What a weird year 1999 was. This wasn’t just the end of the 90s decade, but it’s also the end of the 20th century. After this will be the beginning of both a new decade and a new century. The music of 1999 was a perfect representation of the hectic times and for the most part, it was okay, but a bit of a step-down from 1998. The pop stars have gotten younger with the boy bands and teen idols taking over the charts. Rap and R&B continued doing well and so did rock. The Latin explosion occurred where Hispanic artists (Enrique Iglesias, J. Lo, Ricky Martin, Marc Anthony, etc.) started seeing commercial success. Ladies and gentlemen, we’re at the end of the 90s, so let’s count down the terrible ten and party like it’s 1999.



Well, that’s one way of starting this list. Now, to be fair, the instrumentation to She’s So High is decent enough, but I have two problems with it, Tal Bachman’s voice and the lyrics. The lyrics, of course, suck all kinds of ass. Tal spends most of the song complementing some chick and saying how perfect she is, comparing her to Cleopatra, Aphrodite, and Joan Of Arc, painting her into the ultimate Mary Sue. And then when he tries to talk to her, he’s so amazed by her beauty that he’s speechless and realizes that they weren’t meant to be. It just doesn’t work for me. Even if I could ignore them, there’s also his voice to contest with. My God, his voice annoys the living crap out of me, especially in the chorus when he tries to hit a high note and fails. Every time I hear that chorus, it’s like a rusty scalpel getting jammed into my cranium. There’s just no way for me to like this crap and I’m glad this guy this guy never got another hit.


The picture of a young woman who looks the camera. She has straight brown hair and wears soft make-up. At top the image, the words "Britney Spears" are written in white cursive letters, while at the bottom "...Baby One More Time".

I’m going to say something that will shock absolutely nobody, I don’t like Britney Spears. To me, she was the perfect representation of both generic, manufactured pop music and the music industry’s tendency of¬†overlooking talent for image. Britney’s music has never been that good. At best, her stuff was okay like Sometimes, Lucky, Stronger, and Toxic, at worst, they’re just awful. Her first single Baby One More Time falls closer to the latter. On a surface level, it doesn’t seem that bad, a bit generic maybe. But when you get past the production, that’s when the stench gets worse. The writing of this song is laughably ridiculous. Basically, she’s dealing with the aftermath of breaking up with her boyfriend and her feelings. It’s pretty much by-the-book and doesn’t do anything new with how melodramatic it is, saying she can’t breathe without him and how she shouldn’t have let go and wanting him to, quote, hit her one more time. I hope she isn’t implying being punched in the face because what kind of abusive relationship were you in? Be grateful you’re away from this asshole. Britney has never been a good singer and this song shows how subpar she is. The most positive things I can say about Baby One More Time? It is catchy and it wasn’t the worst song that Britney has ever released, but is that really saying much when the bar is set pretty low?¬†Still, she is capable of doing worse.

Black-and-white image of the upper body of a brunette woman standing in a dressing room. She is wearing a dress and white fedora. The image has a purple border. On the left, the word "Britney" is written in purple cursive small letters. On the center right, the words "Gimme more" are written in purple small letters.


NSYNC, why do you always find a way to end up being made fun of on this site? It’s not like I hate the group because I don’t. They have good songs, but dear Lord, this is not one of them. (God Must Have Spent) A Little More Time On You is sappy contemporary Christian crap. The instrumentation is a bit too sugary for my taste and the guys do sound good, but they’re brought down by the lyrics. It’s one thing to make a song about how beautiful a woman is (I mean, we’ll never run out of songs like that), but this? God must have spent a little more time on you. Fucking barf. This is the shit some drunk asshole at a bar would say trying to pick up a woman to have sex with her before receiving five fingers and a palm to the face. The rest of the lyrics are just awkward rejected Hallmark card quotes. This song is also tied with the cover that country band Alabama did (with NSYNC providing backing vocals), which I think is worse with the instrumentation and vocals. NSYNC, you’re better than this.


While we’re talking about boy bands, New Kids On The Block had already broken up by this point in the decade and the guys have went on their solo ventures. Two of them, Jordan Knight and Joey McIntyre scored top 10 hits with Give It To You and Stay The Same. Give It To You might as well be a 90s Robin Thicke song, which makes sense considering that Robin Thicke is credited as one of the writers. It’s a sleazy sex song with the charisma of dried-up dog shit that features some wonky freestyle production that starts off with carnival music. Because that’s one way to set the mood for some fucking, with carnival music. On the other hand, Stay The Same is a boring ballad that not only features some awful singing from Joey McIntyre (especially when he attempts a falsetto), but it also has some stupid lyrics. The premise of the song is that he wants this girl to stay the way she is, even despite lines like this…

I think that you could be whatever you wanted to be
If you could realize, all the dreams you have inside.

… which contradicts the whole “and I hope you always stay the same” thing. Also, the song goes full gospel right at the final chorus. This and Give It To You can go straight to hell.


Yep. Destiny’s Child is on this list and I’m not even joking. For the longest time, their single Bills, Bills, Bills has irritated me and I now know why. The production isn’t bad and the girls (well, to be accurate, it’s Beyonce and Kelly doing most of the work) sound alright, but it’s the lyrics where this song falls apart. Basically, they want their boyfriends to pay ALL the bills in the house, from the phone to the car notes, because apparently, he doesn’t pay for everything. Okay, you’re dealing with a lazy bum. Here’s my question, though, why don’t you break up with him and kick him out? He’s clearly not going to be beneficial to you being a couch potato, so kick his ass out. You sitting there complaining isn’t going to help matters. This attitude does nothing but turn this into another man-bashing song. I sure hope that when Beyonce goes solo, she doesn’t make a career off these type of songs. No, that’d be silly.


Can’t do a Worst Songs list without mentioning at least one bad hip-hop song, can I? And boy, is this a doozy. Who Dat by Miami rapper JT Money. The production on this song has not aged well, it’s not even the good kind of dated, just the forgettable bland dated. And it nearly drowns out the vocals. Here’s the hook.

Who dat who dat who dat who dat who dat who dat who?
Who dat who dat who dat tryin to get up in my crew?

Well, I hope you like that because it takes up the majority of the song. Nice to know that lazy songwriting is timeless. Content-wise, there’s not much to this song as it’s your typical “can’t nobody fuck with my clique” song and JT Money himself sucks as a rapper. Dude got no presence or charisma at all to the point where he gets sidelined by Sole, the guest featured rapper (even then, she wasn’t that special, either). This song also drags at just 4 minutes, but it feels like 10 while listening. There really is no reason to come back to this song, which makes me question why it was a hit in the first place.


Sixpence None The Richer’s Kiss Me is what I like to call teen drama music. Why? Because it sounds like the type of shit you would hear in teen dramas and funny enough, this song got famous off of teen dramas. The instrumentation is every boring acoustic pop ballad that you’ve heard a bunch of times and just adds to the cheesiness of the song. The lead singer sounds pretty good, but it means nothing because the material she’s given sucks. The lyrics to this song are terrible. They’re like something straight out some angsty teen’s poetry book with all of the pretense and awkwardness. It seems they wanted to make a poetic love song, but when you have lyrics like “kiss me out of the bearded barley,” you’re doing something wrong. No more teen romances, please.


Shania Twain, one of the most successful country acts of all time and is also considered to be a sellout. With music like this, that isn’t entirely wrong because there is NOTHING country about That Don’t Impress Me Much. This production is a sloppy glob of pop shit that wouldn’t sound out of place in a Britney Spears album. People (rightfully) shitting on Taylor Swift, Thomas Rhett, Sam Hunt, and Luke Bryan now for being more pop than country, Shania was just as bad. Granted, I never heard much of her music, but the songs from her that I did hear, including That Don’t Impress Me Much, didn’t impress me much. Outside of the terrible production and meh vocal performance, I have a much bigger issue with this song. How do I put it? Shania Twain is a bitch. She’s way too picky about the kind of guy she likes and isn’t clear about what she wants. She’s not impressed with a guy who’s smart or good-looking? You know? Things that most women look for in a guy. Shania doesn’t even talk about what DOES impress her and ultimately comes off as conceited. You know what doesn’t impress me much? Being an asshole.


*cringes* This song makes my skin crawl and looking at this artwork isn’t helping. This is singer-songwriter Shawn Mullins and his only hit single Lullaby, which is douchebag rock to the core. For most of the song, dude doesn’t even sing, he just talks in a creepy ass sleazy whisper like he’s trying to impress some chick he’s hitting on over some slow bland rock instrumentation. It reminds me of something Sam Hunt would have made. All while telling a boring ass story about a girl who’s bored of her Hollywood lifestyle and wants something more exciting. Meanwhile, Shawn Mullins himself shows up to sing a lullaby to her.

Everything’s gonna be all right
Rock-a-bye, rock-a-bye
Everything’s gonna be all right
Rock-a-bye, rock-a-bye, rock-a-bye

Seriously, how old is this woman and why are you singing a lullaby to her? Lullabies are used to help babies and little kids fall asleep, why are you trying to put people to sleep? Urgh, fuck this douchebag and this song.

Before we get to number one, here are some dishonorable mentions.


  • Sugar Ray-Every Morning
  • Celine Dion & R Kelly-I’m Your Angel
  • Mariah Carey ft Jay Z-Heartbreaker
  • 98 Degrees-The Hardest Thing
  • Lou Bega-Mambo No. 5
  • Blaque-808
  • Silk-If You
  • Mark Chesnutt-I Don’t Want To Miss A Thing
  • Kenny Chesney-How Forever Feels
  • Puff Daddy ft R Kelly-Satisfy You

And finally, the worst song of 1999 IS……

drum roll


Didn’t expect this, did you? Yep. The worst song of 1999 comes from the Backstreet Boys for a song that is overplayed, overhyped, and isn’t as great as people made it out to be, which speaks a lot about the music-buying public of that year and YOU SHOULD SEE THE LOOK ON YOUR FACES!! I’M JUST FUCKING WITH YOU!! AHAHAHAHAHAHAHAHAHAHA!!

Now that I played with your emotions, let me make it up to you by showing the real number one.


This is the most obvious choice for number one, but sometimes, the obvious choice is the correct one. Everyone has torn apart Summer Girls and pointed out everything that’s wrong with it. Hell, even Eminem made fun of it in one of his songs. I’ll be here to reiterate those points in my own way. This is LFO, a boy band whose name is an acronym for Lite Funkie Ones. You wish I was making this shit up. Summer Girls is the textbook definition of a bad song. Nothing in it works. The beat is limp and cheap as fuck and these dudes have the charisma of moldy bread. And instead of singing, they’re rapping and the rapping sucks hippopotamus testicles. You’ll get better raps from Slim Jesus. But the reason why this song sucks so much is, of course, the lyrics. For a song called Summer Girls, it doesn’t really talk about girls in the summer that much as these dickbags spend more time making a bunch of unrelated dated pop culture references that doesn’t connect to each other and some really bad punchlines. This shit is the music version of those Aaron Seltzer-Jason Friedberg spoof movies like Epic Movie, Meet The Spartans, and Disaster Movie. It has no reason to exist outside of being a joke and it’s not even a funny one at that. You had one job, LFO, and you managed to fuck it up. Congratulations to Summer Girls for being the worst song of 1999.

So those were the worst songs of 1999. Now for some announcements. I’ve spent nearly a year going through Billboard Year End Hot 100 charts from the 90s and I had a lot of fun discovering old songs, songs that I hadn’t heard before, finding new favorites, and tearing apart the bad songs. Sadly, our journey through this great decade is coming to a close. Next month, BACK TO THE 90s concludes with what will be my biggest list of the entire site, the 100 Best Songs of the 90s. What better way to celebrate making ten Worst Songs lists than making a huge Best Songs list? Because of the size of the list, it will most likely be split into two parts. Stay tuned for that. Then, the month after, I will start my journey BACK TO THE 2000s with the Worst Songs of 2000. And for those wondering, yes, I am planning to do lists based off the Year End lists of every year tracked by Billboard, so after I’m done with the 2000s, I’ll be doing the 80s, 70s, 60s, and 50s. The journey will be long, but it’ll be all worth it. We are going to have fun, ladies and gentlemen. There won’t be any new posts next week since it’ll be my Spring Break and I need to take a vacation from this site. Be sure to look out for the Updates page as I’ll announce my schedule for the next three months. That’s all I have for now. Thank you for reading and I’ll see you in the next two weeks.

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Stronger-Kanye West

December-Collective Soul

What About Your Friends-TLC

Love Me Harder-Ariana Grande ft The Weeknd

15 thoughts on “Top 10 List: Worst Songs of 1999

  1. My thoughts on the list:
    10. Radiohead’s Creep gone horribly wrong. Do I really need to say more?
    9. Pretty generic, but not too horrible. And she’s done much worse.
    8. I hate Contemporary Christian songs and this is no exception.
    7. Two boring songs from two boring artists from the same band. I fell asleep listening to both.
    6. Not their worst song, but not even close to being up with their best work.
    5. Was this guy asleep at the wheel when writing this?
    4. Didn’t listen to it, and I’m glad I didn’t.
    3. Did Ms. Twain decide to win “Bitch of the year” or what?
    2. *Cringes*
    Real 1. You took the words right out of my mouth.
    Also, that was a great April Fool’s prank. You should do another one next year.


  2. You must have added Give it to you and Stay the Same after featuring the songs in a target practice. Stay The Same is a snoozer song.


  3. OK Seriously! Is there something about Kiss Me that I just don’t hear? That’s one of my favorite songs of all time, and now this is like the second or third worst songs list I’ve seen it on.
    I love EVERY lyric of the song. I love the acoustic guitar riff throughout the song. I love the accordion solo in the middle, and the lead singer’s voice is beautiful! What am I not getting?


  4. That was a clever joke you played there; one of the best April Fool’s jokes ever.

    Anyways, I am really looking forward to the upcoming Worst Songs of The 2000s lists because that was the decade I grew up in. I can see why you took down your original one because you wanted to start over. My predictions for No. 1 are:

    2000: Higher by Creed
    2001: Butterfly by Crazy Town
    2002: How You Remind Me by Nickelback
    2003: Mesmerize by Ja Rule featuring Ashanti
    2004: F It (I Don’t Want You Back) by Eamon (It would have been tied with F U Right Back by Frankee had the latter charted like in the UK, where I live)
    2005: My Humps by The Black Eyed Peas (obviously)
    2006: London Bridge by Fergie
    2007: Crank Dat by Soulja Boy (obviously)
    2008: Lollipop by Lil Wayne featuring Static Major
    2009: Party in the USA by Miley Cyrus (granted, this was before she became what she is today, but still…)


    1. Complicated and Toxic for #1 worst songs of 2002 and 2004. Former because she’s a pathetic Britney clone attempting to be Alanis, and the latter is, well, obviously Britney.


      1. I doubt you’re going to get your wish with Toxic since B-HOP just called it one of her okay songs.

        I hope Complicated isn’t on the list because I genuinely enjoy that song, though it’s not the best single off of Let Go. I like some good pop rock, and Avril Lavigne, along with people like Michelle Branch and P!nk, were a breath of fresh air for me back in the early 2000s.


  5. Smells Like Teen Spirit for #1 Best Song of the 1990s. It’s on the same boat as Goodfellas by Martin Scorsese and Pulp Fiction by Quentin Tarantino.


  6. I’ve always liked She’s So High because I can relate to building someone you like up in your mind and then lacking the confidence to tell them how you feel. Baby One More Time is a bit of a guilty pleasure, and Kiss Me is just kind of a pleasant, nostalgic song for me. On the other hand, I totally would have bought I Want It That Way as the worst song of 1999 because I’ve never liked it or the Backstreet Boys much at all. So yeah, pretty big change from 1998 where I agreed with pretty much everything, but I still really enjoyed the list.


  7. YOU MOTHERFUCKER! DON’T TOY WITH ME LIKE THAT! I feel like just for that, you should add I Want It That Way to your songs of the week section. Anyway, good list as usual, B-Hop. My disagreements are 10-8, 4, Sometimes, Every Morning, & Back That Azz Up. Also, surprised to see How Forever Feels not in the DHMs given the smug attitude of that song (and this is coming from someone who usually *likes* Kenny Chesney’s music) or (even though I like them) Amazed by Lonestar or Please Remember Me by Tim McGraw given your general distaste for slow ballads like those that could be considered bland or boring (even if I don’t think so myself).


    1. Best April Fools prank ever. Totally worth it. Please Remember Me wasn’t bad enough to make the final cut (not saying they’re good) and I’m saving Amazed for 2000.


      1. I was actually about to bring up that you missed Amazed by Lonestar but I kind of assumed since it peaked higher in 2000 than in 1999 that it would count for that year.


      2. Unpopular opinion, I actually don’t like “I Want It That Way”, at all. I don’t think it’s as great as people say. It’s just more generic boy band schlock, and every time I hear it I’m annoyed by it.


      3. After doing target practices on Stay The Same and Give it To You, these songs entered the list. In addition to latin music, Nu Metal and rap metal was gaining footing on the charts and 1999 was the beginning of Eminem with the song “My Name Is”


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