30 Celebrity Comebacks That Bombed and Why

Top 30 Worst Celebrity Comeback Fails

Welcome to WatchMojo, and today we’re counting down our picks for the most unsuccessful rebound attempts by celebrities. To keep this list from getting too long, we’ll be excluding athletes.

#30: Justin Timberlake

Despite being a part of an infamous wardrobe malfunction and an even more infamous relationship, this NSYNC star managed to dodge controversy throughout most of the 2000s. But, eventually, it all caught up to him, and it had Timberlake fans saying “Bye, Bye, Bye” for good. The sentiment is reflected in his newest music, none of which has connected the way you’d expect from such a name talent. In fact, the only time Timberlake’s made headlines the past few years is when he got pulled over for allegedly drinking and driving, spawning a whole internet meme about his world tour. Backstreet is most definitely not back.

#29: Shane Dawson

This YouTuber has always been marred with controversy. From tasteless jokes to questionable company, Shane Dawson’s never been in the clear. But, up until a few years ago, it didn’t matter. His compelling docu-series’ and thorough conspiracy videos put him at the very top of the YouTube hierarchy. Then, it all came crashing down. Dawson’s work with contentious figure Jeffrey Star broke the camel’s back, opening him up to all the controversies he’d been brushing to the side. Since then, Dawson’s issued a few apologies and kept on making videos. But, it’s clear from the views that most of his audience has already jumped ship.

#28: David Hasselhoff

Sorry David, no matter how iconic it may be, no one can make a whole career out of slo-mo running on the beach. After “Baywatch” ended in 2001, the actor’s time in Hollywood was left without a life preserver. Despite incredible name recognition, it seemed like people just weren’t interested in Hasselhoff unless he was the butt of the joke. He tried to turn things around with a Kardashian-like reality show, but it was embarrassingly canceled after just two low-rated episodes. Since then, Hasselhoff has paid the bills with cameos, music, and stints in theater, but nothing near the caliber of his earlier work.

#27: Mýa

You’ve gotta respect any artist with the tenacity to start their own label. Then again, Mýa’s fall from grace is a perfect example of why it’s so difficult. Once a certified triple threat, Mýa’s time on her own has turned her career prospects from bad to worse. Instead of a major event, her new releases feel like a drop in the bucket. For what it’s worth, Mýa tried to rejuvenate interest in her brand with the debut of her alter ego, Mya Lan$ky. But, at this point, there just aren’t enough people still listening to care.


#26: Farrah Abraham

The novelty of “Teen Mom” is that they’re, well, teenagers. So, when MTV decided to phase out the aging original cast, Farrah Abraham was left without a very strong resume. She attempted to pivoted her image with a New York Times best-selling memoir and a strange accompanying album.And then… nothing. Abraham simply couldn’t springboard “Teen Mom” into any kind of long-lasting success, and it’s not for a lack of trying. For a while, it felt like she was boarding every reality show that would have her. These days, when you hear about Farrah Abraham, it’s usually not for a good reason.

#25: Limp Bizkit

Ironically, Limp Bizkit’s nu metal sound inspired many of the bands that would replace them. You can blame it on any number of reasons; the infamous bandmate feuds, the diminishing music quality, or the failure to adapt to the times. Either way, the fact of the matter is that Limp Bizkit faded hard and fast. They tried to rebound in 2011 with the buzzy album, “Gold Cobra.” But, by then, they were too old school for new fans, and too different for veterans. While Limp Bizkit has continued to throw new songs at the wall, something tells us nothing will be sticking any time soon.


#24: 50 Cent

Arguably one of the most prominent rappers of the 2000s, 50 Cent’s work in the 2010s left a lot to be desired. Paired with a series of highly-publicized lawsuits, and the artist’s time in the limelight seemed to fizzle out for good. You don’t just have to take our word for it, though. The numbers don’t lie. The year after his supposed comeback album bombed, 50 Cent filed for chapter 11 bankruptcy. He’s spent the last several years slowly rebuilding his brand. But, considering how poorly his first attempted revival went, we aren’t holding our breath.

#23: Kirk Cameron

This guy went from teen heartthrob to divisive has-been in record time. Even though “Growing Pains” made Kirk Cameron an overnight sensation, his extreme religious views limited the kinds of roles he’d accept. It stalled his career for years, and unfortunately, the projects he did board weren’t exactly winners, either. 2014’s “Saving Christmas” was supposed to kickstart his second wind in evangelical media. Instead, it’s often considered one of the worst movies ever made, period. That, along with some very aggressive political views, have kept Cameron off screens for years now. He’ll need more than a Christmas miracle to get back on track now.

#22: Kanye West

It’s genuinely shocking to live in a world where Kanye West just released a new single, and no one seems to care. To be fair, though, this is a mess of his own making. While West has never shied away from taboo topics, his antisemitic remarks in 2022 proved to be several steps too far. His inflammatory comments cost him sponsorships, friends, and just about every shred of audience goodwill he had left. Later, West tried to shove it all under the rug with a new lead single, “Vultures.” Based on the lukewarm reception, he won’t be reaching his peak again any time soon.

#21: Chevy Chase

Once an undisputed king of comedy, what happened to this actor’s career is no laughing matter. Chevy Chase burnt his capital starring in one-too-many flops, and by the time the late 2000s rolled around, he was in dire need of a hit. Thankfully, he got one in “Community.” Chase’ turn as the egotistical Pierce Hawthorne put him back in everyone’s good graces. At least, until we got wind of his on-set behavior. Chase's behind-the-scenes antics were so abhorrent, “Community” killed his character offscreen in the middle of season five. Fittingly, it also ended any chance Chase had at a real career resurgence.


#20: Bill Cosby

Bill Cosby spent most of the 70s and 80s playing good, honest men on TV screens everywhere. After all, you don’t get a name like “America’s Dad” for nothing. But, just when he was starting to do the same in the 2010s, the other shoe dropped. Over sixty different women stepped forward accusing Cosby of gross sexual indecency across his career. To say audiences were blindsided would be an understatement. Immediately, several of his awards were revoked, and reruns of his programs - including “The Cosby Show” - were pulled from syndication. Forget a comeback; Bill Cosby doesn’t even have a legacy anymore.


#19: Steven Seagal
No one is above the law - even an actor who starred in a movie literally called “Above the Law.” While Steven Seagal’s martial arts fight scenes turned him into a bonafide action hero, a series of personal stumbles dimmed the shine on his Hollywood star. Alongside diminishing returns on the action front, and it’s no surprise Seagal has spent the last twenty five years working almost exclusively in low-budget, direct-to-DVD flicks. None of them have broken into the mainstream, but that hasn’t stopped Seagal from making them. He hasn’t had time to do much else on account of all the lawsuits, allegations, and scandals, anyways.


#18: Ray J
This rapper hit his peak in the mid 2000s. His fourth studio album, All I Feel, reached #7 on the Billboard 200 chart, and its lead single, “Sexy Can I,” reached #3 and went platinum. Every one of his subsequent singles have failed to chart on the Hot 100, with the exception of “I Hit It First,” which reached #51 in 2013. The song makes reference to the adult film “Kim Kardashian, Superstar,” featuring his ex and himself and released in March of 2007. The 2010s has seen Ray J hosting Oxygen’s “Bad Girls All-Star Battle” and competing on both “My Kitchen Rules” and “Celebrity Big Brother.” The latter stint only lasted a week, as he left the show after blacking out from tooth pain.

#17: Denise Richards
This ex-fashion model was quite a big name in the late ‘90s and early 2000s. She starred in the likes of “Starship Troopers” and “The World Is Not Enough” before marrying Charlie Sheen. They were married from 2002 to 2006, and their messy divorce kept Richards in the spotlight. Despite some valiant efforts, Richards hasn’t been able to reclaim her past glory. She has starred in many B-movies and a few short-lived TV shows, as well as being a regular on soap opera, “The Bold and the Beautiful.” Like many attempting a comeback, she has also transitioned to reality TV, joining the main cast of “The Real Housewives of Beverly Hills.”


#16: Ciara
This R&B artist was huge throughout the 2000s and early 2010s, with four of her first five albums peaking in the top five. Her second, Ciara: The Evolution, reached #1 in 2006. Her singles also performed well. “Goodies” peaked at #1 in 2004, and both “1, 2 Step” and “Oh” reached #2. Following “Love Sex Magic” in 2009, none of her singles have breached the top ten. She has remained in the spotlight thanks to public relationships with rapper Future and NFL player Russell Wilson, but her music career isn’t what it once was. Her last two albums, Jackie and Beauty Marks, reached #17 and #87 respectively on the Billboard 200..

#15: Mischa Barton
Entertainment Weekly named Mischa Barton “The It Girl” of 2003 owing to her work as Marissa Cooper on “The O.C.” The show ran for four seasons between 2003 and 2007. Barton starred in the first three before her character was killed off in the third season finale. Ever since then, Barton has struggled to retain her It Girl status. She has appeared in many independent films and competed on “Dancing With the Stars” in 2016. However, she was just the second person eliminated. She too eventually went the reality TV route and joined the cast of “The Hills: New Beginnings” in 2019.


#14: Iggy Azalea
This Australian rapper burst onto the scene in history-making fashion. Literally. She became just the second artist in history to hold the top two spots on the Billboard Hot 100 with their debut entries on the chart in 2104. The Beatles did it in 1964 with “I Want to Hold Your Hand” and “She Loves You,” and Azalea poetically matched it fifty years later with “Fancy” and “Problem.” She was a guest artist on the latter, but the record still counted. Unfortunately, her star has since fallen from grace. In My Defense reached #50, a far cry from The New Classic’s peak at #3. Her last single to peak in the top five was “Black Widow” in 2014, with none of the singles from In My Defense even breaching the top fifty.



#13: Jennifer Lopez

Careers can live or die based on a comeback album. Sadly, JLO swung, and missed - bad. Her attempted return to form, called “This Is Me… Now,” marked the lowest debut of any of Lopez’s studio albums, ever. To make matters worse, the songs were supposed to tie into a multimedia project, including a feature film and a nationwide tour. At least the movie came out. That’s more than we can say for the tour, which was quietly canceled. It’s a good thing Lopez has been consistently starring in Netflix films, because on the music front, she’s all but dead in the water.

#12: Ashlee Simpson
This younger sister of Jessica Simpson made some waves in the mid 2000s with her albums Autobiography and I Am Me. Both reached #1 on the Billboard 200, both were certified platinum (with Autobiography going 3x platinum), and “Pieces of Me” proved a big hit, peaking at #5 on the Hot 100. Unfortunately, Simpson hasn’t released any music as a solo artist since 2008, aside from a non-album single in 2012 that failed to chart. She’s now part of a duo called Ashlee + Evan with her husband Evan Ross, and they released an EP in 2018 that failed to generate much discussion. They also launched an E! reality show, but that only lasted for six episodes.

#11: Fergie
Like many on this list, Fergie was huge in the 2000s. She was obviously a big part of the Black Eyed Peas, but she also saw success as a solo artist with The Dutchess. Released in 2006, The Dutchess reached #2 on the Billboard 200 and was certified 5x platinum. The album also spawned three number one singles - “London Bridge,” “Glamorous,” and “Big Girls Don’t Cry” - and one number two with “Fergalicious.” After about a decade away (aside from a song on “The Great Gatsby” soundtrack), Fergie returned with Double Dutchess. It wasn’t nearly as successful. It only reached #19 and failed to generate any successful singles. The most successful, “"L.A. Love (La La),” peaked at #27.

#10: Paris Hilton
Despite coming from an uber successful and unfathomably rich family, Paris Hilton made a name for herself through modeling and reality TV. She notably starred on “The Simple Life” alongside Nicole Richie from 2003 to 2007. While her dumb blonde, spoiled persona was obviously played up for the camera, the show made her insanely famous. Most of that fame came at her own expense, but she clearly didn't care. And while she’s still making bank through her numerous business ventures today, Hilton’s public spotlight has faded. She has dabbled in DJing in recent years and went back to reality TV with Viceland’s “Hollywood Love Story,” but that came and went. She was also the subject of a YouTube Original documentary titled “This Is Paris” in 2020.


#9: Vanilla Ice
Vanilla Ice became a worldwide megastar with “Ice Ice Baby.” The song was an enormous hit, peaking at #1 in eight different countries, including the United States and Zimbabwe. In fact, it made history by becoming the first hip hop single to reach the top of the Billboard Hot 100. Ice took a break from music in 1993, but when he returned, his subsequent records received little fanfare. He did find success with his DIY Network show “The Vanilla Ice Project,” thanks to his experience in home improvement. In 2011, he released his comeback album W.T.F. (Wisdom, Tenacity and Focus). It was not a success, and Vanilla Ice hasn’t charted on the Hot 100 as a lead artist since “Cool as Ice” hit #81 in 1991.

#8: Katherine Heigl
Another big 2000s star, Katherine Heigl first gained some fame in 1999 starring as Isabel Evans on The WB’s “Roswell.” She rode this role to greater success, including her Emmy-winning performance on “Grey’s Anatomy” and movies like “Knocked Up” and “27 Dresses.” That time would prove the height of her career. She has since starred in many movies, but none of them were very popular or that good. Most of Heigl’s work can be found on television. The mid-to-late 2010s saw her star in “State of Affairs,” “Doubt,” and “Suits.” The first two were cancelled after just one season, and her role in “Suits” lasted two. Heigl is still receiving steady work, but the recent TV comeback fails to match her “Grey’s Anatomy” heights.


#7: Guns N Roses
This hard rock band was once one of the biggest in the world, with their first four studio albums reaching either #1 or #2 and selling over five million copies each in the United States alone. Things slowed down with 1993’s The Spaghetti Incident?, as it only reached #4 and ended the band’s multi-platinum run. It would be fifteen years until the band returned, and the results were underwhelming. On November 23, 2008, the world finally received Chinese Democracy, which received middling reviews and only sold one million copies. The long-awaited comeback was completely dead in the water. Luckily, both Slash and Duff McKagan saved the band by touring with Axl and company on the incredibly successful Not In This Lifetime Tour.

#6: Lil’ Kim
This New York rapper got her start through The Notorious B.I.G. by joining his group, Junior M.A.F.I.A. This led to a highly successful solo career throughout the late ‘90s and 2000s, which included three top ten albums. 2001 also saw her singing “Lady Marmalade,” the highly successful single from “Moulin Rouge!” But like Guns N’ Roses, Lil’ Kim took a major hiatus. There was a fourteen year break between 2005’s The Naked Truth and 2019’s 9, and the wait was… not really worth it, according to most accounts. The album received mixed reviews from critics and performed poorly, failing to land on any major charts or generate any notable singles.

#5: Tara Reid
This American actress had quite a respectable movie career throughout the late ‘90s and early 2000s. She appeared as Bunny in “The Big Lebowski” and went on to star as Vicky in the “American Pie” franchise. Rounding out her filmography were works like “Josie and the Pussycats,” “My Boss’s Daughter,” “Van Wilder,” and a stint on “Scrubs.” Something happened around 2005, and Reid just… disappeared. Not completely, as she was still in things, but the hits had certainly dried up. Reid then tried her hand at reality TV, including “Celebrity Big Brother” and her own show “Taradise” before settling on the B-movie turned cult “Sharknado” series.

#4: Ellen DeGeneres
There once was a time when Ellen DeGeneres was the biggest name in entertainment. Her historic coming out as a lesbian both paved trails and ignited controversy, and her follow-up talk show proved enormously successful. While coming out nearly tanked her career, it was the talk show that ultimately did. In 2020, Buzzfeed reported through anonymous employees that working for Ellen was akin to hell on earth, complete with harassment and racist comments. While her show wasn’t cancelled, the eighteenth season premiere faced significant backlash. Outlets criticized her opening monologue, and the YouTube video’s like to dislike ratio skews heavily towards the latter. It was also reported that the show’s premiere week viewership was down 30% from last year.

#3: Ja Rule
This rapper released a string of successful albums throughout the late ‘90s and early 2000s, six of which peaked within the top ten on the Billboard 200. These include Rule 3:36 and Pain Is Love, both of which reached #1 and both of which were certified multi-platinum. However, Ja Rule has subsequently faced numerous legal issues throughout his career, including a two year prison sentence in 2010 and another 28-month sentence the following year. He was released in 2013, and just three years later started the infamous Fyre Media, Inc. It could have been a huge business and public comeback, but the Fyre Festival proved so disastrous that he faced a $100 million class action lawsuit instead.

#2: Charlie Sheen
By 2010, “Two and a Half Men” was proving so popular that Charlie Sheen was earning nearly $2 million per episode. However, his personal life wasn’t nearly as triumphant. Sheen was well known for his substance abuse and reckless behavior, with especially the latter allegedly aimed towards his then-wife Brooke Mueller and the trashing of a hotel suite. He was eventually dismissed from “Two and a Half Men,” and while the resulting press put him in the news, the termination effectively killed his career. Sheen attempted a comeback with roles in “Scary Movie 5” and a show called “Anger Management,” and while the latter ran for 100 episodes, it received poor reviews. The comeback was a fail, and Sheen hasn’t been seen in movies or on TV since 2017.



#1: Roseanne Barr
Few comebacks have crashed and burned like this one. Barr’s sitcom “Roseanne” was a huge hit throughout the ‘90s, remaining a top four show for six of its nine seasons. It came to a controversial end in 1997 with a divisive series finale. Luckily for fans, it was revived by ABC and brought back for a tenth season in 2018. It was actually a huge success, with the premiere episode generating nearly 20 million viewers. It lasted all of two months. Barr made a comment that was deemed racist on Twitter, which she proceeded to blame on Ambien. The show was immediately cancelled amidst the controversy, as was Barr herself. She once again faded into irrelevancy, and everyone else moved on to “The Conners” without her.



Did we miss any celebrity comeback flops? Let us know in the comments below!