
500 Miles – The Proclaimers

Had they managed to land a couple more successful hits anywhere outside of the UK, the Scottish Twins might have escaped the fate of over-exposure. It’s quirky, upbeat, and easy to sing along to, which is great for a flash-in-the-pan pop track but the lack of substance to grasp onto makes the tone feel almost mocking. We get it, you love getting your steps in.
Crazy Frog – Axel F

What was a classic addition to the pantheon of 80s movie songs you could drive down the strip to in the scorching sunset, is now forever linked to a cartoon frog and his cartoon frog genitals. It could have been worse, nothing from Rocky IV got ruined, but the Crazy Frog joke was long dead before they decided to give him a theme song.
The Final Countdown – Europe

Okay, the synth riff is catchy, but the composition is bog standard and it relies far too heavily on the guitar drumming out those triplets to give it any sense of momentum or drive forward. Plus lyrically like what is going on? Presumably, the final countdown was the launch to Venus, so why are there like 12 more of them left?
Cotton Eye Joe – Rednex

You’d think you couldn’t make a plantation work song a pop super hit, but then you’re probably not a Eurodance group from Sweden. Everything about this is offensive. The attempted accents, the grating banjo and fiddle production that takes away any semblance of authenticity, and the fact it’s clearly a gimmick song, which only works if you’re weird and named Al.
Believe – Cher

Before the rhinestoned crucifix is erected, Cher has some phenomenal work in her catalog. Believe is not one of them. Though it was the largest-selling single of 1999, it signaled a lot of 2000s music sins to come. Simple, and repetitive, the drum machine high-hat sits in the mix like a stone in the center of your brain. Okay, continue erecting.
Who Let The Dogs Out – Baha Men

You might assume the lyrics are the issue here, since you can only remember they do, at some point, ask who let the dogs out. A surface-level glance tells you the dogs are a metaphor for the boys, they’re out partying, getting rejected by women but being comfortable with that and moving on. It’s a good enough message – it’s everything else that’s dreadful!
You’re Beautiful – James Blunt

Blunt himself is aware of the hatred surrounding his most famous track and frequently pokes fun at it on his social media profiles. That does alleviate the melodrama somewhat but, still, it’s not got enough self-awareness to justify writing such a tragically pathetic song. The narrator is a character and all we get in our brief time with them is that they see someone so beautiful, they just want to die.
Disco Duck – Rick Dees and His Cast of Idiots

Joke songs run the risk of getting stale much quicker than a standard pop tune. Comedy has a much shorter shelf life generally and finding a button that makes your Casio keyboard screech like a duck is funny for about three seconds. Where did the inspiration come from to turn that into a full disco-inspired audio assault? 1976 Memphis, baby.
Photograph – Nickleback

A lot of the hate toward Nickleback’s is unfounded. Some of their earlier work is dramatic and grungy enough to get some joy out of but, somewhere along the line, they nailed the radio-friendly, cool Canadian dad pop-rock that would earn them the ire. Photograph isn’t their worst but opening a song with an impossible visual command a songwriting deadly sin. How am I meant to look at it, Chad? How?
Baby – Justin Bieber

It sounds crass at this point to dunk on Baby but, as Bieber matured into an artist with at least his own sound as the years went on, Baby remains his worst track. The instrumental sounds cobbled together with stock, unmixed samples, and, matched with his understandably shrill register, all make something far too sickly-sweet.
De Do Do Do, De Da Da Da – The Police

The Police are excellent songwriters and riff makers and, although the song isn’t without its hooks, the repetition feels unearned. It’s not an unpleasant listening experience and the lyrics do have their own important meaning as they echo the empty platitudes spouted by those in power, but you can do that in a good song too! Surely Sting knows that.
Livin La Vida Loca – Ricky Martin

Once the soundtrack to dark and humid 90s nights, Martin’s post-boyband, Latin-infused pop-ballad is now a sober reminder of the metro-sexual era. It’s all surface-level suave, it’s trying to be passionate but there’s no soul or rhythm in there. It’s too uptempo to be a good addition to a bedroom playlist, and you’ll be distracted thinking about Shrek 2. Insert Puss in Boots joke.
My Humps – The Black-Eyed Peas

The scientific consensus has shown that the stress from societal pressures to conform to specific body types causes much more harm to people than their weight does. This is why the body positivity movement is so important… and why rhyming humps with lumps is just a deeply unflattering use of semantics. We tend to panic when we find lumps in our bodies, thanks Fergie.
Sherry – The Four Seasons

This song came out in 1962, which most music historians believe was after the invention of the bass clef, making the group’s refusal to use it on this track a mystery. It’s likely a combination of the recording and mastering technology of the 60s, but the piercing quality and basic repetition make this song feel like little more than white noise.
Ice Ice Baby – Vanilla Ice

When a society would sooner see washed up celebrities and drunken karaoke groups sing the song for laughs, you know you’ve dropped a stinker. Yes, it essentially steals the bassline from Queen and Bowie’s Under Pressure, but that isn’t necessarily a crime. Music is built on expanding past ideas, but Mr. Ice adds nothing to the song.
My Heart Will Go On – Celine Dion

Few performers have as much genuine power in their vocal performances as Dion, and her work over the years has never really faltered. Still, 2023’s most popular news story so far has shown that aquatic disasters are still a source of great interest… perhaps explaining why the song’s initial Heart has soured after so, so many years of Going On.
Thong Song – Sisco

It’s got the vibe of a comedy song but is delivered with the earnestness of a young man who thinks this is his magnum opus. Sisco himself has surmised as much, justifying his crimes with “I was young.” Thongs are funny when you’re young, it’s something you’re not supposed to see and you get a quick giggle. Not a number one, Grammy-nominated hit.
Friday – Rebecca Black

Song’s garbage, whatever. The real moral of Friday is music-industry guys who hang out in the mall and prey on young girls with aspirations and parents with projection issues, should probably be in jail. Black is still doing music despite the incredibly disproportionate anger the world threw at her, making her braver than every country artist combined.
Achy Breaky Heart – Billy Ray Cyrus

Nobody should be shamed for expressing themselves through art, but a Big Tough Cowboy man talking about how his achy breaky heart doesn’t understand why you don’t love him anymore, like a 12-year-old would do, is objectively funny. The rest lacks much of note, except the quickly grating country twang of his voice.
Macarena – Los Del Rio

Finally, a dance for white people. This is the precursor to a lot of the aforementioned TikTok songs, essentially made in a lab for people to dance in place to for a few seconds. Like those, it has nothing to offer outside of a beat simple and slow enough for everyone to process where their hands are in preparation for the next step.
Blurred Lines – Robin Thicke

There are quite a lot of people involved in modern pop production, and how so many thought this was a good idea continues to baffle the world. Conceptually it is just about pushing the boundaries of consent, half-sang, half-smugly schmoozed by a man who refuses to accept how old and gross he is. It would have been massive in the 50s.
I Want Candy – The Strangeloves

Although it came first, the key and rhythm were sadly done much better in George Michael’s Faith. That isn’t an accusation of plagiarism, the wonderfully groovy rhythm is called a clave and derives from Afro-Cuban music, the holy spirit of which is carried into Faith with much more aplomb. Also, the vibes of this song are just sickly-sweet enough to make your teeth hurt.
Mah Na Mah Na – The Muppets

The Muppet’s purpose with this song was to entertain children, and in that sense, they succeeded. It entertained everyone for a second, with its catchy folk-like non-lyrics and silly dancing. In many ways it was the Baby Shark of its time, becoming an instant rage trigger for those with children.
Cheerleader – OMI

Another song that, removed from its context, just offers no reason to re-visit. Jamaican artist OMI was already established in his home country, but Cheerleader launched his laid-back fun-in-the-sun vibes across the globe. There’s no sense of evolution in the song, no dynamic range, or interesting harmonic choices to keep you even remotely paying attention.
Baby, I’m Good – Andy Grammer

There’s nothing more romantic than a heartfelt love song about how your man could totally cheat on you whenever he wants. He doesn’t want to cheat, he’s good, even though if he did it wouldn’t be hard. He could have someone over in like 15 minutes. It wouldn’t even be a big deal, she would know it wasn’t going anywhere. Anyway, love you babe. Gross.
I Whip My Hair – Willow Smith

Since everybody is talking about showbiz nepo-babies, here’s an example of why they’re a bad idea. Anybody can write good music, it just takes time and practice and sucking for a while. Celebrity children don’t get to experience that in private like everybody else. Your kid sucks, man, encourage them and get them lessons – not a recording contract.
I’m a Gummy Bear – Gummibär

Like the Crazy Frog, this was written to be annoying. In the era of texting numbers you saw on TV to get custom ringtones, the only thing you needed to be to make money was obnoxious. Not much has changed, but even in its time this little guy seemed exceptional at his job. At least this one is wearing some pants.
Happy – Pharrell Williams

Don’t let anybody tell you that you don’t deserve to be happy! Equally, don’t let Pharrell tell you to be happy – if that contradiction makes sense. For a slightly more complicated version of If You’re Happy (And You Know It), this song was truly inescapable. Every department store felt like some giant daycare center, blasting music for little idiot babies (us!).
Grenade – Bruno Mars

There’s a kind of contradiction in pop music, where to be broadly marketable songs have to appeal to as many people as possible. That leaves Bruno talking about the various ways he would tear himself to shreds for some nondescript woman he loves so much. Love isn’t an active war zone, at most, you just have to say you would love them even if they somehow turned into a worm.
Jam – Kim Kardashian

For Kim, an entire music career was something she could get done on a moderately busy Tuesday afternoon. Her wealth and connections mean that, at most, she delivers a couple of lines and then clocks off to go to the money store. The production is, as expected, mostly all there is. Nobody involved cared about this, it’s just an artistic vacuum.
It’s Peanut Butter Jelly Time – The Buckwheat Boyz

The 2000s online world was very much the wild west, nothing was safe or regulated, and you needed to keep your wits about you. Many older hits were repackaged as memes – Never Gonna Give You Up and Mah Na Mah Na are perfect examples. Some people, though, just wanted to make their own. It succeeded in a way, making something one-note enough for Family Guy to pay attention.
U.G.L.Y – Daphne and Celeste

As an early example of a diss-track, this ranks quite highly on the list. Without the associated context of knowing who the target is, we don’t have any reason to support D and C in their bullying. Then they bring the mother into it? What are the chances both the girl and her mom deserve the drag, come on now. Play nice.
“The Ketchup Song (Aserejé)” – Las Ketchup

According to Las Ketchup, the song is meant to be a chance to experience the social awkwardness of not knowing how to dance. This fits the song’s chaotic composition, with tempos, beats, and syncopation placed seemingly at random. It’s impossible to fall into the rhythm of the song, which made its popularity bizarre.
We Like To Party – The VengaBoys

Eurobeat is an acquired taste. Not everyone is into thumping techno, raving, or body paints, and it’s unlikely even those people would listen to this one in the sober light of day. Referred to by many as the low point of pop, The VengaBoys are partly behind the false idea that European techno is mindless babble spread in the first place.
You’ve Got The Love – Florence and the Machine

For as magnificent as Flo’s voice is, You’ve Got The Love is just so uninspired. Everything is far too clean and predictable, it feels manufactured almost. Perhaps that’s the idea, with Florence’s Machine beep booping the song out. Instead, though, it comes across less as an artistic decision and more like they wanted this to be used in car commercials for the next decade.
Moves Like Jagger – Maroon 5

Ignoring Levine’s penchant for scandal and messaging fans behind his wife’s back, he also writes some truly dreadful radio pop. The word toothless springs to mind, every edge and point of interest sanded down until you have a perfect sphere. But, with no friction, it quickly slips out of the brain and you can know peace again.
She’s So Lovely – Scouting For Girls

British pop-rock fell off during the 2000s, and American pop-punk had become the new hit thing. Fall Out Boy and Green Day ruled the airwaves and kept Warped Tour in business. These clever lads shook things up by adding a keyboard, a slightly cleaner Brit-pop adjacent image, and it lead to some decent songs. The three-word chorus gets boring two words in though.
Right Round – Flo Rida

If you’re going to borrow your hook from Dead or Alive, try and give it a little bit of sass. The original’s repetition is underlined by a fantastic beat, with layers adding texture you can’t help but bob your head to. Flo Rida brought nothing to the table, just a sort of crass, unearned confidence. It’s like his Thanksgiving parade performance all over again.
Hey, Soul Sister – Train

Most of Train’s music sounds AI generated. Just a mismatch of everything that’s vaguely popular at that moment, packaged together with the most basic arrangement and chord progressions. If Alien’s had only heard Maroon 5 and thought that was the only example of music that existed, they’d come up with something similar. But with lasers.
Thinking Out Loud – Ed Sheeran

The idea of owning a chord progression is silly and it’s for the best that Marvin Gaye’s two lawsuits failed. That having been said, Gaye self-reported a little bit by trying to stake a claim on one of the most popular sounds in the Western canon. It was dull when Gaye did it… it felt like a bludgeon to the head when Sheeran tried.