Top 20 Worst Comeback Songs of All Time

#20: “Rock Show” (2001)

Run-DMC feat. Stephan Jenkins

Like ketchup and ice cream, Run-DMC and Third Eye Blind are two great things that would be terrible together. As music trends shifted with the rise of rap-rock, Run-DMC felt their sound was getting a bit stale. Their solution was to collaborate with artists like Stephan Jenkins, frontman of Third Eye Blind, to try to capture some of that new sound. The result is a song that feels awkward and forced. Stephan Jenkins is barely utilized on the track, leaving him to mostly just stand idly during the music video. “Crown Royal” was the group’s last album before the death of Jam Master Jay, an incredibly disappointing release compared to their previously groundbreaking material.

#19: “Boyz” (2021)

Jesy Nelson feat. Nicki Minaj

This song is significant for being a debut, a comeback, and a flop all at once. This former Little Mix member was set to kick off her solo career with this risky single featuring popular but controversial rapper Nicki Minaj. The song debuted at No. 4 on UK charts, but quickly fell as critics and fans alike began tearing the song to shreds. Complaints ranged from excessive autotune to cultural appropriation and blackfishing. No one was happy with this solo debut, and Nelson’s career was pretty much dead on arrival. And the cherry on top of this disaster sundae – a music video cameo that could not have aged worse.

#18: "Sonic Boom” (2009)

Kiss

Ten years after their previous album release and a whopping 35 years since their debut album, the 70s-era glam metal band Kiss released “Sonic Boom” in 2009. There isn’t just one song that can be singled out from this terrible comeback, so we’ll consider the album as a whole. “Sonic Boom” was intended to prove that Kiss was still culturally relevant, and able to compete with other, younger, musical acts rising in popularity. After all, nothing says “cultural relevance” like a Walmart-exclusive album. The album was disappointing to existing fans and completely ignored by potentially new Kiss fans, and sold a pretty dismal 238,000 units throughout 2009.

#17: “Half of Me” (2013)

Geri Halliwell

This famous former Spice Girl will always be a cultural icon for her Union Jack dress, but her solo career was slightly less iconic. She initially enjoyed modest success for her solo work, particularly in Australia, but after 2005 she paused her music career to pursue other ventures. Eight years later, Halliwell attempted to revive her career with “Half of Me,” a single released exclusively in Australia. When Aussies failed to connect with the Brit’s song, Halliwell quietly stopped promoting it. She has since shifted her focus to other projects, including directing, acting, and writing.

#16: “Peanuts 2 N Elephant” (2025)

Lil Wayne

After making fans wait five years for new solo music, Lil Wayne came out with this song that definitely doesn’t live up to his legendary reputation. Produced by Lin Manuel-Miranda, of “Hamilton” fame, the song's instrumentals sound straight out of an old video game. Lil Wayne’s rapping isn’t much better, coming across as lazy and lifeless. Coming from two musicians with a solid hitmaking reputation, this was a shockingly bad end result. Maybe Wayne is working on a circus-themed video game? Truly, there’s no other explanation for this.

#15: “Pretty Girls” (2015)

Britney Spears and Iggy Azalea

After the lukewarm release of her eighth album, “Britney Jean,” Britney Spears stopped releasing new music for nearly two years. Her first release after her hiatus was a collaboration with an Australian rapper who was making big waves in the pop world. “Pretty Girls” received mixed reactions, with some critics calling it catchy if a bit formulaic. While Spears managed to pull off a career renaissance in the late 2010s, Iggy Azalea didn’t fare as well. Accusations of cultural appropriation and delays to her second studio album completely halted the progress of her once-promising career.

#14: “Pretty Girls” (2025)

Will Smith

Though his career might still be in desperate need of some rehabilitation after the infamous Oscars incident, Will Smith’s return to the music industry probably isn’t getting the reaction he was looking for. Aged 56 at time of writing, it seems Smith has lost some of his signature charm in the decades since he graced our screens as the Fresh Prince. As a result, his song intended to convey his admiration for beautiful women just comes across as a bit sleazy. Maybe this song could have worked twenty years ago, but now it just makes us desperate for a flash from a Neuralyzer.

#13: “Big Hoops (Bigger the Better)” (2012)

Nelly Furtado

This Canadian singer gifted us with some serious bangers in the early 2000s, ones that still hold up today like “Maneater” and “Promiscuous”. Furtado released a greatest hits album in 2010, and we thought that was that. Then, two years later, we got “Big Hoops.” While the song isn’t bad per se, her vocals were frequently compared to Rihanna, and the whole song is just steeped in 2012 “swagger-culture”. Furtado has continued to release new music, albeit quite sporadically. Since her attempted comeback with “Big Hoops,” none of her releases have even come close to her former glory. We’re still happy to keep the old stuff, though.

#12: “Dumb Blonde” (2019)

Avril Lavigne feat. Nicki Minaj

As the ultimate pop-punk cool girl of the early 2000s, many of us looked up to Avril Lavigne for her stylish image and rebellious attitude. “Dumb Blonde” was never part of her reputation, so this 2019 attempted comeback made little sense to begin with. The song marked a return to Lavigne’s early 2000s sound, but it doesn’t measure up to hits like “Girlfriend” and “Complicated.” Critics compared the song’s sound to “Hollaback Girl,” a much more popular song by another blonde alternative pop princess. And of course, the ultimate “Dumb Blonde” track had already been released over fifty years earlier by the legendary Dolly Parton.

#11: “Chasing the Sun” (2014)

Hilary Duff

Following early hits for this former Disney Channel star like “Why Not” and “So Yesterday,” Hilary Duff took a break from the music industry to focus on her acting career. After a few less-than-positively received performances that failed to shake her wholesome child-star image, Duff turned back to music in the early 2010s. “Chasing the Sun” was set to be her big musical comeback, a breezy summer tune penned by Colbie Caillat. The result, however, was completely bubblegum bland, devoid of any original sound. Duff released a few more singles and an album a year later, but for the most part her music career fizzled out entirely. Now a mother, entrepreneur, and children’s book author, Duff seems to be doing just fine without it.

#10: “Can’t Get Enough” (2024)

Jennifer Lopez

J.Lo’s 2024 has been one for the books — and by that, we mean a series of post-apocalyptic novels. A decade after her previous studio album, Lopez returned to music with an album, film, and planned tour all titled “This is Me… Now.” The new era celebrated her reconciliation and marriage to ex-fiancé, Ben Affleck, which she called “the greatest love story never told.” Unfortunately, things got off to a rocky start with lead single “Can’t Get Enough.” It wasn’t terrible, but it sounded just like her 2000s hits from the first go-around of Bennifer, without much evolution. Besides the song’s underperformance and derivative nature, its lyrics and wedding-themed video aged poorly: Lopez and Affleck announced their second split before the year even ended.

#9: “Get Her Back” (2014)

Robin Thicke

The jury on his career was looking blurry, but after this song, his comeback clearly wasn’t happening. On “Get Her Back,” Robin Thicke laments his split from his estranged wife, actress Paula Patton. Not only was the song a far cry from the immediate catchiness of “Blurred Lines,” but it overestimated the amount of public interest in his personal life. While Thicke may have been a solid B-list name, it relied on the mythology of his and Patton’s relationship and banked on people caring about their separation more than they actually did. Lightning probably wouldn’t have struck twice if Thicke had recreated “Blurred Lines,” but “Get Her Back” didn’t even come close to what made that song such a hit.

#8: “Slow Clap” (2021)

Gwen Stefani

This song is B-A-N-A-N-A-S — specifically, the peels that make you spin off track in Mario Kart. Gwen Stefani’s “Slow Clap” was the second of two singles meant to kick off her fifth solo album, but contrary to the title, it was mostly met with crickets and tumbleweeds. The song, which features Saweetie on the remix, would sound right at home in a Dreamworks movie or a back-to-school commercial. The music video’s gymnasium setting is a clear nod to Stefani’s past hit “Hollaback Girl,” but it feels like a juvenile, hollow attempt at recreating the latter’s magic without any of its edge. Seeing as its parent album never came, “Slow Clap” seemingly killed the era. Someone probably should have told her to put the pom-poms down.

#7: “Pom Poms” (2013)

The Jonas Brothers

After a brief hiatus to pursue solo ventures, the Jonas Brothers were ready for their triumphant return with the release of “Pom Poms” in 2013. The song was catchy, but the lyrics were nonsensical and a bit too juvenile for a group attempting to ditch their Disney image. Judging by the song’s reception, the world wasn’t ready for a JoBros comeback, and apparently neither was the band. They split before the release of their planned album, citing creative differences. Thankfully, their 2019 comeback was much more well received and gave this band of brothers the renaissance we were all hoping for.

#6: “Yummy” (2020)

Justin Bieber

With his 2015 album “Purpose,” Justin Bieber seemingly achieved the impossible. He successfully shed his uncool teenybopper rep, and people who weren’t tweens could openly admit to liking him without ridicule. Unfortunately, this shift had a momentary dip with his next lead single, 2020’s “Yummy.” More of a TikTok sound bite than a full-fledged song, it was nonsensical, repetitive, and made people question his rehabilitated image. Unlike many of the other songs here, “Yummy” was a major hit and didn’t derail Bieber’s career. However, its inescapability added to its annoyance — even though it was universally panned, it was still absolutely everywhere. Despite the lyrics and visuals bringing to mind a stomach or toothache, it was really our ears that suffered with this one.

#5: “Karma” (2024)

JoJo Siwa

With “Dance Moms” and YouTube fame, JoJo Siwa built a media empire on rainbows, glitter, and countless brand deals before she even reached adulthood. Like many child stars, she soon felt she had outgrown her kid-friendly image, and longed for a rebrand. “Karma” was intended to usher in a new era for Siwa, and apparently pop music entirely according to the singer. She swapped neon rhinestones for black ones, and dropped this tune that the internet absolutely ripped to shreds. It was painfully obvious that Siwa was no bad girl, despite how desperately she wanted to appear like one. Time will tell if she’ll ever be able to recover her image from this major flop, but so far it’s not looking good.

#4: “Too Cold” (1998)

Vanilla Ice

This comeback was a brand new invention in some ways, and a retread of old ground in others. Eight years after the success of 1990’s “Ice Ice Baby,” Vanilla Ice released his third album, “Hard to Swallow.” Rather than continuing the playful pop rap of his early career, it adopted a totally different sound: nu metal. The lead single, “Too Cold,” was a reworked version of “Ice Ice Baby” in the style of Korn and Limp Bizkit. While the genre shift was an admirable creative risk, it omitted the original’s iconic piano rift lifted from Queen and David Bowie’s “Under Pressure.” “Too Cold” briefly gave Vanilla Ice’s career a second life, but it didn’t fully materialize into a successful long-term crossover.

#3: “Filthy” (2018)

Justin Timberlake

After his squeaky-clean hit “Can’t Stop the Feeling,” JT trolled us all with “Filthy.” The lead single of Justin Timberlake’s “Man of the Woods” album, it managed to crack the top 10 of the Billboard Hot 100 but lacked the longevity of his previous eras. “Filthy” is somehow all over the place and forgettable at the same time — it doesn’t measure up to his past hits, nor does it commit to the album’s Americana inspirations, leaving it stuck in an awkward limbo. Timberlake’s more recent output isn’t faring much better, with his 2024 singles “Selfish” and “Drown” failing to get in sync with listeners.

#2: “M.I.L.F $” (2016)

Fergie

This song walked so her national anthem disaster could run. Nearly a decade after her debut solo album, “The Dutchess,” Fergie was gearing up for its follow-up, “Double Dutchess.” Its lead single, “L.A. Love (La La)” had already been out since 2014, and 2016’s “M.I.L.F. $” was set to reignite the era. However, not even the song’s star-studded music video featuring Kim Kardashian and Chrissy Teigen could offset its abrasively busy production and grating vocals. There’s certainly a conversation to be had about ageism faced by female singers, but Fergie’s ode to sexy motherhood was just plain obnoxious. After “M.I.L.F. $,” it wouldn’t be shocking to see an ad for her career on the back of a milk carton.

#1: “Woman’s World” (2024)

Katy Perry

Sometimes, it only takes one song for an artist’s career to go from “American Idol” to “American Horror Story.” Katy Perry was already struggling since her 2017 album, “Witness,” severely underperformed, but the rollout of “Woman’s World” was an utter disaster. The song was panned for its dated sound, shallow pop feminist lyrics, and production from Dr. Luke, the subject of singer Kesha’s allegations. “Woman’s World” was especially frustrating because it could have gone differently if Perry played her cards right. In the year of Chappell Roan and Sabrina Carpenter, the greater pop landscape was the closest it’s been to her campy style in recent memory, and the hype was there. Unfortunately, the song missed the mark, crushing any hope of a comeback.

Which of these artists deserve a second chance at a comeback? Let us know in the comments!