Music

The 10 Cringiest Pop Songs from the 2000s

The 10 Cringiest Pop Songs from the 2000s

It’s hard to think about the music that came after 2000 and before 2010.

Filled with a seemingly endless collection of plastic, surface-level pop songs that served no purpose other than to dominate the radio and wriggle themselves into our eardrums, the first half of the 2000s was a special kind of terrible.


As trashy as pop music was in those dark years of low rise jeans and jelly sandals, there were a handful of tracks that stood above the rest. Whether it be Ashlee Simpson dissing her mom or a 13-year-old Aaron Carter rapping about “honeys,” it’s hard to believe the following tracks were as popular as they were. Here are the cringiest pop songs from the 2000s.

“My Humps” by The Black Eyed Peas

While Fergie may have been the track’s main protagonist, she had 0 input on any of “My Humps’s” titillating lyrics–which instead were all written entirely by will.i.am. It’s uncomfy in 2021 to think of a grown man sitting down and writing, from a woman’s perspective, things like, “I say no but they keep given’, so I keep on takin.'”

Music critics initially derided the track, noting its repetitive nature and “controversial” content. Still, it was a smash hit and was so embedded into pop music that it eventually won a Grammy for “Best Pop Performance by a Duo or Group with Vocals.” Still, It’s a cringe record in and of itself, and it’s hard to imagine a song like “My Humps” existing today without Meg Thee Stallions’ input.

“Outta My Head (Ay Ya Ya)” by Ashlee Simpson

At one point in history, The Simpson sisters were somewhat prevalent in popular culture. Jessica, the eldest of the two, was marketing the hell out of her marriage to Nick Lachey (more on him later), while the youngest was striving to establish herself in the realm of pop-rock music.

It was kind of working. “Pieces of Me,” Ashlee Simpson’s debut single, did fairly well on the Billboard Hot 100, peaking at number 5. The track chronicled a young Ashlee amidst the thrills of a new relationship. It was a simpler track for a simpler time. But by 2008, Ashlee’s next big single was aimed at someone in particular, although she denied it profusely. “It’s not about my mom,” she told MTV in 2007 after rumors swirled of mother-daughter beef. Regardless, the track is definitely about her mom.

“Aaron’s Party” by Aaron Carter

It’s crazy to say, but in 2021, we are all still painfully aware of Aaron Carter. His grotesque face tattoos and cringe antics have kept the former child star in the spotlight for all the wrong reasons (he is currently training for a boxing match with Lamar Odom.) To reflect back on “Aaron’s Party” in the wake of all this drama is to see the track as a cry for help. The poor boy is so devoid of a sense of identity that he rapped a song about partying and talking to “honeys” at age 13. Anyways, the song went 3x platinum. Does that say more about him or us?

“Trouble” by Never Shout Never

Back when emo music reigned and toxic sad boy misogyny bordered on cool, there was a song called “Trouble.” The track found singer Christofer Drew bleating for a girl he loved and continuously harassed. “I called so many times, I swear she’s going mad,” he yodels.

To make matters worse, Christofer also can’t stop “running his mouth” to his friends about how he’s in love with her. The track, with its infectious chorus and simple uke melody, exploded on MySpace, with hundreds of fans polluting YouTube and school talent shows with their own versions. While many found the track cute and charming from the jump, its sheen has all but disintegrated by 2021.

“Stars Are Blind” by Paris Hilton

“Stars are Blind” by Paris Hilton was plugged into every conceivable music outlet when it was released in 2006 and received a plastic reggaeton remix by Wisin & Yandel that somehow gained monumental radio traction overseas. The track was somehow digestible at the time, its mid-tempo reggae fusion making the vibe feel breezy and lighthearted. Even now, we’re all humming the chorus as we read this article. Were we brainwashed as a culture, or just completely devoid of taste? We may never know.

“What’s Left of Me” by Nick Lachey

As one of pop culture’s early “It” couples, Jessica Simpson and Nick Lachey’s romance was well-documented in both a successful reality show and in the tabloids. The couple’s saturation in the media inevitably led to their demise in 2008, but Nick still had one card left up his sleeve: to woo his ex-wife back into his life by writing a hit song.

“What’s Left of Me,” a piano-driven ballad that says nothing and everything simultaneously, tore up the radio and landed at number 6 on the Billboard Hot 100. The melodramatic music video sprinkles hints throughout that the track is about Jessica and mourns the life they led in front of cameras. Sure, the track is cheesy beyond belief now; but back then, it was the f*ckboi anthem: the underlying soundtrack to toxic middle school relationships. The “I’m-so-sorry-I-hooked-up-with-your-best-friend” type of song. The “I-got-demons-that-I’m working-on” type of song. These were simpler times.

“True” by Ryan Cabrera

But before Nick Lachey, there was Ryan Cabrera. The spiky-haired pop-rock singer had a few mediocre hits throughout his tepid career, but we all remember him for that toxic temper tantrum he threw on 2004’s “True.” “I won’t talk, I won’t breathe / I won’t move ’til you finally see that you belong with me.” The toxic masculinity of the 2000s was truly something to behold.

“I Like To Dance” by Hot Chelle Rae

Hot Chelle Rae recently got back together at the request of absolutely no one, but for a moment in time, they were relatively popular in the dance-rock realm. “I Like to Dance” was one of their biggest early hits and remains about as satisfying as biting into decorative fruit. The crazy thing is these Nashville rockers were actually gaining momentum. They supported Taylor Swift and Demi Lovato on tour, and they had a platinum record by 2011. Then, they suddenly just vanished come 2016. But again, they “reunited” in 2018, so, I guess, yay?

“Love Drunk” by Boys Like Girls

Speaking of Taylor Swift, remember when she recorded a duet with Boys Like Girls? For a split second, and I mean for one and a quarter album cycles, Boys Like Girls were seemingly the next big pop-rock group. Their debut track, “The Great Escape,” slowly crept up the charts, and by “Love Drunk” the Boston-based band was positively buzzing. “Love Drunk” attempted to recapture the youthful break-free energy of “The Great Escape,” its sweeping chorus and rocking power chords uplifting and exciting in a “my crush just messaged me back” type of way. But by the band’s third album, the buzz fizzled out as fast as a fleeting summer romance.

“Bad Day” by Daniel Powter

Let’s make one thing clear: Daniel Powter’s “Bad Day” is still awesome. Who else has curated a hit song based on just a lousy day? With that said, it’s still kind of silly thinking about how big of a hit the track was. It was the first song to ever sell two million digital copies in the US and was eventually certified 3x platinum in the US, as well as platinum in five other countries.

It was the most played song on European radio; and the track’s music video, which merely chronicles the bad days of a few people, was the eighth most-watched video on the internet in 2006. The question remains: Why did “Bad Day” explode the way it did? (The answer: It was the eliminated loser’s soundtrack on American Idol. Nevermind, solved it).

Up Next

Don`t miss