Worst Songs List

Top 10 List: Worst Songs of 2008

2008 is a year that’s special to me. It was my freshman year in high school and I became more interested in music. At the start of the year, I dropped the Radio Disney crap for something more… sophisticated. It was also the year Barack Obama was elected President of the United States. It was a time for hope in the face of an economy going down the toilet. I wish that I could say the same about the music, which was still stale from the previous years. 2008 was a transition year, one that had no solid trend. Crunk was dying off as it was replaced by club music. There were fewer and fewer rock songs that made any significant impact. Alternative’s own weird niche was growing. Pop divas were making a comeback while new ones were on the horizon. It was a weird year. So let’s dig into the worst that ’08 had to offer.



Jesse McCartney - Leavin'.jpg
Jesus, this could be a poster to a horror movie.

Hey, does anyone remember Jesse McCartney? This dude was a staple among the Radio Disney crowd with bland pretty boy schlock. Then he grows up and wants to be taken more seriously as most former kid stars do and the result of that is Leavin’. Eww. Just… eww. First off, the production is weak. It’s this K-Mart pseudo-R&B crap with whistling synths, awkward percussion, and random cell phone noises that won’t shut the fuck up. This kind of production could’ve only existed in the late 2000s and it has aged badly. Jesse McCartney himself has always fallen under the category of “safe, non-threatening white guy” and this song doesn’t change that. He wanted to be the successor of Justin Timberlake, but he doesn’t have the charm or charisma to pull it off. And we haven’t even gotten into the lyrics, which are basically a fusion of Post To Be by Omarion and Treat You Better by Shawn Mendes. Guess what Leavin’ has in common with these two songs? Yep. It’s another “I can steal your girlfriend” song. Oh, joy.

I know you got a man but this is what you should say

Why don’t you tell him that I’m leavin’ never looking back again
You found somebody who does it better than he can
No more making you cry
No more them gray skies
Girl we flying on a g-5, g-5
And we’re leavin’ never looking back again
So call your shawty you tell him you found a new man
The one who’s so so fly
The one to keep you high
Have you singing all night, like that

Suck. A. Dick. Go suck a dick until your jaw is numb and you’re unable to taste anything. Get this self-absorbed pandering shit out of here.


In the Ayer cover.jpg

The number one song of 2008 according to Billboard was Low by Flo Rida and does anyone remember ANYTHING from the song outside of the T-Pain hook? No, they don’t. Flo Rida himself was barely a presence in his own song, which is a fact about all of his songs. But we’re not talking about Low. Instead, we’re gonna talk about another bad song, In The Ayer. Oh, this song is a disaster. The hook is awkward and stilted, just like everything else in the song. will.i.am demanding people to put their hands in the air just doesn’t register thanks to his nasal, droning voice. The beat is a series of preset loops with the impact of a grain of sand. Of course, will.i.am was behind the production boards for this creatively empty shell. As usual, nothing Flo Rida has ever rapped sticks, it enters one ear and exits out the other. He’s the physical embodiment of tumbleweed. In The Ayer just doesn’t work as a club song since it doesn’t have the energy or punch to get people moving. Sadly, this won’t be the last we’ll hear from the android known as Flo Rida.


Pocketfulofsunshinehz7mvf9.jpgNatasha Love Like.jpg

I hate Pocket Full Of Sunshine. If that makes me Satan, then I’ll gladly wear the horns because I can’t stand to hear this thorn in my ass cheek for another second. This is one of those songs where overplay pretty much soured my opinion on it. But overplay isn’t an indicator of quality, so it’s lucky that I have other reasons to not like this happy-go-lucky piece of crap. There’s nothing wrong with it writing-wise and while the production is super lightweight, I’ve heard worse in other songs, but it is so goddamn repetitive and annoying. The song is 75% bridge and chorus and it keeps repeating ad-nauseum. Not helping is Natasha Bedingfield sounding like she’s teasing the listener and screeching at the top of her voice. Every time I hear this song, I want to punch the closest thing that breathes. If Hell had a mixtape, this song would definitely be in it. Now that I’ve gotten my rant on Pocket Full Of Sunshine out the way, let’s talk about Natasha’s other turd from 2008, Love Like This. This is obviously the worse song out the two. While Pocket Full Of Sunshine was tailor-made to torture me, Love Like This is just incompetently put-together. There’s this artificial, fake-R&B production that feels less soulful and more cynically calculated. The breezy piano, the dusty drums, the weird pitch-shifted vocals, the Auto-Tune. If anything, it feels like a white-washed recreation of Kanye West’s production style from his first two albums. Why the hell is there Auto-Tune on Natasha’s voice? It sticks out in random, inappropriate moments in her singing that it further exposes her flaws as a vocalist. Also, what the hell is Sean Kingston doing here? This is just one of those tacked-on features that the record executives selected out of throwing darts at a wall of names. The song is about old friends hooking up for nostalgia sake and this doesn’t work when you have a 26 year old white woman from the U.K. singing with a teenage pop “reggae” artist from Jamaica. I’m starting to think that Unwritten, Natasha’s only good song, was a fluke because this, plus Pocket Full Of Sunshine, is just a miscalculated catastrophe of music.


A three-quarter portrait of a female teen facing left. Her eyes look toward the viewer and her hand is placed on the top of her curly, dark brown hair.

Image result for trigger warning

Well, this day was inevitable. In 2008, the Disney Channel sitcom Hannah Montana was HUUUUUUGE. Not only did it give Billy Ray Cyrus relevance, but it made a star out of his daughter Miley. I’m not gonna mince words: I can’t stand Miley. Aside from Hannah Montana being an entry to the LONG list of bad Disney Channel sitcoms, I always found her screeching voice irritating as all hell and her music ranged from generic schlock to audio torture. Case in point, 7 Things. If someone doesn’t know what a bad teen-pop song sounds like, point them to this. All of the ingredients needed to make Radio Disney fodder is present. You have the thin, flavorless pop rock instrumentation that rocks with the intensity of watching grass grow. It blends in perfectly with the other synthetic teen-pop songs that Disney was pooping out. This song is Miley bitching and complaining after breaking up with one of the Jonas Brothers. It’s one thing to write about how you’re feeling mentally, but when that writing doesn’t have any maturity to give the subject some type of weight (not helped by weak vocals) it doesn’t make for a compelling listen. It might as well be another one of Taylor Swift’s numerous break-up songs. God, this song sucks so much.



Oh, look, it’s Chris Brown. Never expected to see you again on a Worst Songs list. *sarcasm* Chris was already off to a bad start with his debut single, but that was only an appetizer for what’s to come. And thus, we arrive to Kiss Kiss. What’s there to say about Kiss Kiss? It’s a song that makes you want to punch the nearest person in your vicinity. The production is this buzzing array of synths and blocky percussion, that sets a creepy, uncomfortable vibe. Even worse, Chris Brown is a creep stalking some chick like a lion hunting a gazelle. This is Street Harassment: The Song. Any dude who tries to say the things Chris said in this song should be guaranteed a foot to the family jewels and a restraining order. His vocals are grating, which isn’t helped by the Auto-Tune. T-Pain shows up not only for a hook, but he also contributes a rap verse because bananas. And it shows why T-Pain should stick to singing.

Shawty let me holla at you
you so hot-hot-hot-hot
you think I’d be holing
if you not-not-not-not
I’m king of the town
you can take a look around
Teddy Penderazzdown
is in the spot-spot-spot-spot
(Yeah) I got money on me
(Yeah) Baby girl no problem
(Yeah) You rolling shawty?
(Yeah) Lets hit McDonald’s
It’s T.P. and C.B.
I’m the nappy boy — ooh weee!

Seriously, is he out of breath or something? This is pathetic, along with the rest of this goddamn song. And to think that Chris Brown would only get worse later on with his horrible behavior being more present.


Lil Wayne - Lollipop.jpg

Oh, I’ve waited too long to talk about this godawful dumpster fire of a song again. Lil Wayne was pretty much the biggest rapper of 2008, overshadowing titans like Jay Z, Kanye, and T.I. with his biggest album to date, The Carter III. And the album wasn’t that great. Why? Because of songs like Lollipop. Fuck Lollipop in the ass. Nearly everything wrong with hip-hop in the late 2000s was part of this sour turd. The beat is probably the best part of the song in spite of its 4-note bleeping synth melody. Then we get to the rest of the song. This is another example of Auto-Tune abuse in songs as Lil Wayne is crooning horribly in yet another sex song that uses candy as a double entendre for a sexual act.

She lick me like a lollipop (I like that)
She lick me like a lollipop (I like that)
She lick me like a lollipop

And that pussy in my mouth had me loss for words

Call me so I can make it juicy for you
Call me so I can get it juicy for you
Call me so I can make it juicy for you
Call me so I can get it juicy for you

All of the lyrics are Lil Wayne drowning in a pool of punanny. You know the fucked-up part? As terrible as this song is, it’s not even the worst song from 2008 that uses candy in a sexual context. No, that goes to the next song.


Three 6 Mafia - Lolli Lolli (Pop That Body).jpg

This can’t be real, right? There’s no way it can. It has to be some elaborate joke being played on the public. Ladies and gentlemen, this is Three 6 Mafia’s Lolli Lolli (Pop That Body). People actually made this a hit? How? Why? This is shit. Listen to that beat and its stiff percussion, schizophrenic synths, and wait. Is that piano riff ripping off the Halloween theme? It is. That’s the fucking Halloween theme. Way to make this song even creepier. Every time I hear this song, I expect to see this guy behind me.

Image result for michael myers

The guy singing the chorus should be banned from doing choruses because this chorus sucks hard. The amount of Auto-Tune used in this song should be illegal. Even though this song came out the same year as Lollipop, it has more in common with Laffy Taffy by D4L, mainly in that they’re comparing vaginas to candy, but instead of telling chicks to shake that laffy taffy, they’re telling them to let that lolli pop. GET IT?! LOLLI POP?! LOLLIPOP?! Ugh, whatever. There’s not much to the verses from DJ Paul, Juicy J, and Project Pat, it’s all the things that Three 6 Mafia has rapped about in their songs, only this time, it revolves around strippers. *sigh* I don’t know what else to say about this piece of shit. It speaks for itself.



You know one way to annoy the piss out of me if you’re a music artist? Yell incoherently over shitty production. That’s what Webbie, Lil Boosie, and Lil Phat did on this big hit Independent. This song is best known for its chorus. That awful, awful chorus where Webbie spells the word “independent” in the most ear-scraping raspy voice I’ve ever heard since Plies. It’s such a pain to listen to that I wonder why anyone would subject themselves to it. The beat sounds like a lot of shitty ringtone rap songs of the times; booming bass, ugly synths, gang vocals, etc. The subject matter is all about admiring independent women… just like that other hit song from the same year from a guy named Ne-Yo. Yeah, the only thing Independent has in common with Miss Independent is the subject matter. Meanwhile, it has none of the latter song’s class, grace, intelligence, good writing, good production, good ANYTHING. Hell, they don’t even do the whole “independent women” thing justice as they still talk about her wanting these three to stick their frankfurters into her buns. The amateurish rapping and lyrics all stink of horniness and it’s disgusting. Thankfully, this is the last we’ll hear from Webbie and Boosie on the charts. R.I.P. to Lil Phat, though.


Black and white image of the upper bust of a brunette woman. She is looking into the camera holding a white telephone. She has a white hat in her head. Her hair is falling over her shoulders. Her nails are painted black. She is sitting in a white couch, with her right arm placed behind her head. The upper and lower part of the image are covered in green and maroon lines. In the upper part, the words "Britney Spears" are written in flavescent yellow capital and small letters. In the lower part, the words "Piece of Me" are written in a similar fashion.

Hi, Britney. It’s been a while since I’ve talked about you. At this point in 2008, Britney Spears was trying to revitalize her career after a disastrous 2007 filled with tabloid fodder, bald heads, and umbrella attacks. Unsurprisingly, her first attempt at a comeback fell flat thanks to songs like Piece Of Me. This song is a diss against the media and the paparazzi, which could’ve made for a compelling song, but setting aside the fact that she didn’t write the damn song and the only reason she was relevant at the time was because of the paparazzi, every single element in Piece Of Me has let it down big time. This… this is a train wreck plain and simple. What the hell is going on with this production? It has elements that reminds me a lot of Music by Madonna; the buzzing synths, the hollow percussion, the lack of a cohesive melody, whatever the hell that robotic moaning is. It’s such a slow, sludgy sound that’s hard to listen to without feeling depressed. Britney Spears sounds horrible here. Whatever vocal effects they put on her voice has backfired big time and has only made her sound less human, which makes her shots less convincing. This was the point where Britney was releasing some of her worst music to date and somehow, someway, she manages to keep going downhill.

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


  • Katy Perry-I Kissed A Girl
  • Ray J & Yung Berg-Sexy Can I
  • Mariah Carey-Touch My Body
  • Fergie-Clumsy
  • Jason Mraz-I’m Yours
  • Metro Station-Shake It
  • Buckcherry-Sorry
  • Plies-Bust It Baby/Hypnotized
  • David Banner ft Chris Brown & Yung Joc-Get Like Me
  • Baby Bash ft T-Pain-Cyclone
  • Jonas Brothers-Burnin’ Up
  • The-Dream ft Jeezy-I Luv Your Girl
  • David Archuleta-Crush
  • Kid Rock-All Summer Long
  • Saving Abel-Addicted

And finally, the worst song of 2008 IS………..

drum roll


When I Grow Up.png

The goddamn Pussycat Dolls. I can’t believe I’m talking about them again after 2005’s list, but here we are. And boy, does did they deliver a stinker. When I Grow Up. Where do I even start with this? Ooh, let’s look at the production first. Who in the Nine Realms summoned this demonic collection of irritating noise? Synths that have no sense of direction, some weird creaking sound, there’s nothing in this production that works in its favor. Even worse are the vocals where you can’t tell who’s who and trying to find any sense of personality is about as useful as finding any functioning brain cells in the current White House administration. And now we get into the content, which is the same as Rockstar by Nickleback, where the girls (Nicole) sing about wanting to be famous superstars when they grow up. As I’ve mentioned when I talked about Rockstar, this wish fulfillment crap doesn’t work when you’re already famous and successful. It doesn’t help that there’s a stench of arrogance that spits in the face of the listener while spouting about how cool they are. To the listener, they might as well call them losers and nobodies. And then there’s this line:

Be careful what you wish for ’cause you just might get it

No. You don’t get to earn this line, especially when you spend the entirety of the song talking about how awesome being famous is and never addressing the repercussions of attaining a higher status. It’s like the writers live in a fantasy world where money solves all of your problems. I mean, did you motherfuckers NOT listen to Mo Money Mo Problems? *sigh* After this, the Pussycat Dolls’ time in the spotlight will be cut short and thank God. Congratulations to When I Grow Up for being the worst song of 2008.

So that was the top ten worst songs of 2008. Next month, BACK TO THE 2000s continues with the Worst Songs of 2009.




Little Talks-Of Monsters And Men

More Than A Feeling-Boston

Can You Stand The Rain-New Edition

A Spike Lee Joint-Flatbush Zombies

5 thoughts on “Top 10 List: Worst Songs of 2008

  1. I’m a bit surprised at When I Grow Up being Number 1 on the list but then again, this was mostly because I didn’t have a taste in music back then and just liked whatever was catchy. Same with Piece of Me. On that note, I loved Britney’s music when I was a kid, but then she started doing that crazy stuff that ruined her image.

    As for Leavin’… damn, I thought Treat You Better was bad enough, but this takes the goddamn cake here. Maybe Jesse McCartney and Shawn Mendes would get along very well, what with both songs having a bad message about stealing men’s girlfriends.

    Lollipop is still my worst song of that year though, mostly because of the lyrics. Little did we know that Lil Wayne, Miley Cyrus and Chris Brown would de-volve into something much worse…


  2. Disagreements: Pocketful Of Sunshine, I Kissed A Girl, Shake It, Burnin’ Up, I Luv Your Girl, and All Summer Long.

    Now for what your thoughts on the songs that made my list but not yours

    *Gavin Rossdale – Love Remains The Same

    *Santana ft. Chad Kroeger – Into The Night (this one I’m not sure if you’ll find bad because of Kroeger or bump up to meh/okay because of Santana)
    *Taylor Swift – Love Story
    *Katy Perry – Hot N Cold
    *Jordin Sparks – One Step At A Time


  3. I agree with all your picks, except in the dishonorable mentions I don’t hate Take You There or All Summer Long. And I actually like Low. Yeah, it’s a dumb strip club song and Flo-Rida doesn’t have any real presence, but it’s fun and catchy in my opinion. 2008 in my opinion was one of the worst years in popular music history. There just weren’t that many great songs. Mostly because 2008 was the year where auto-tune REALLY was everywhere. The songs on your best list were among the few good song on that year end list (except “No Air”, don’t really care for that song), and a few more others, but overall, most of the songs were attrocious. Looking forward to what you’re gonna put on the 2009 list.


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