Top 20 Worst Celebrity Comeback Fails

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#20: Ray J

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Top 10 Celebrity Apology Fails

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.

Many child actors flounder after their big show has ended, and Dustin Diamond is one of them. Diamond famously played Screech on “Saved By the Bell,” which ran while Diamond was entering his teenage years. He later reprised the role for “The New Class,” which ran until 2000, when Diamond was 23. And that was about it for him. He went on to direct an adult film titled “Screeched - Saved by the Smell” and released a behind-the-scenes book called “Behind the Bell,” which was fiercely criticized and rejected by his co-stars. He attempted a comeback in 2013 by competing on “Celebrity Big Brother,” but a 2014 arrest and four month prison sentence pretty much ended his career for good.

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, and she is now acting in the 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.”

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..

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.

This Australian singer 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.

The ‘90s belonged to Sharon Stone. She received one Academy Award and four Golden Globe nominations for “Basic Instinct,” “Casino,” “The Mighty,” and “The Muse.” Her role as Ginger in “Casino” was particularly acclaimed, as it won her the Golden Globe and earned Stone her only Oscar nomination. “Basic Instinct” also made her a national sex symbol, and by 1995, Stone had a star on the Hollywood Walk of Fame. Unfortunately, a string of disappointments followed in the 2000s, including “Catwoman” and the embarrassing “Basic Instinct 2,” which essentially killed her career for a decade. Stone has attempted a comeback of sorts, appearing in “The Disaster Artist” and “The Laundromat,” but she has yet to re-capture the magic.

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.

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.

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.

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.

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#9: Katherine Heigl

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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.

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.

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#7: Lil’ Kim

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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.

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.

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#5: Ellen DeGeneres

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Top 10 Worst Things Ellen Has Done

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.

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#4: Ja Rule

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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.

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#3: Charlie Sheen

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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.

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#2: Lindsay Lohan

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The Troubled Life of Lindsay Lohan

There once was a time when Lindsay Lohan was a promising and ambitious actress. But her life and career hit unexpected road bumps in the mid 2000s, and Lohan went through a highly publicized downward spiral filled with bad press, substance abuse, and both rehab and prison stints. 2019’s “Among the Shadows” proved her first feature-length movie in six years, although it was only released through video on demand and received little attention. She also launched her own reality show on MTV called “Lindsay Lohan’s Beach Club,” but it was cancelled after just one season. Her comeback efforts are nevertheless valiant, and she found some success playing Katerina West in the second season of Sky One’s “Sick Note.”

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.