Celebrities Who Ruined Their Career
Claire Miles - September 27, 2019


By Shel Silverstein

My dad gave me one dollar bill
'Cause I'm his smartest son,
And I swapped it for two shiny quarters
'Cause two is more than one!

And then I took the quarters
And traded them to Lou
For three dimes -- I guess he didn't know
That three is more than two!

Just then, along came old blind Bates
And just 'cause he can't see
He gave me four nickels for my three dimes,
And four is more than three!

And then I took the nickels to Hiram Coombs
Down at the seed-feed store,
And the fool gave me five pennies for them,
And five is more than four!

And then I went and showed my dad,
And he got red in the cheeks
And closed his eyes and shook his head --
Too proud of me to speak!

Hollywood has always been a fickle business, and the saying “five minutes of fame” exists for a reason. While some celebrities only had five minutes of fame, others needed only five minutes to end theirs. Whether it was a scandal, a crime, or simply bad choices, these celebrities proved that it doesn’t take long to go from a somebody to a nobody. Here are the celebrities that destroyed their careers in a matter of seconds.


Jennifer Grey


Getty Images/Entertainment/Rodin Eckenroth


Jennifer Grey was one of the biggest female stars of the ‘80s, starring in roles like Jeanie Bueller on Ferris Bueller’s Day Off, and the iconic Frances “Baby” Houseman in Dirty Dancing. Grey’s nose was a prominent feature of hers, but as her career slowed down a bit in the early ‘90s, Grey made a decision that would affect her career in a major way – a nose job. Due to complications in the first procedure, Grey had to undergo another surgery. The operation left Grey unrecognizable even by her closest friends. Speaking on the experience, Grey said: “I went into the operating theatre a celebrity – and came out anonymous.”



Ashlee Simpson


Getty Images/Entertainment/Craig Barritt


Ashlee Simpson was a big star in the early ‘00s. Simpson released her debut single, Pieces of Me, in 2004. The song became a big hit and reached the top five in the U.S. Following the success of the single and the album, Autobiography, Simpson was invited to be the musical guest on Saturday Night Live. Simpson performed two songs on the show. During the second performance, Simpson was set to perform Autograph. However, the vocals for Pieces of Me began playing while Simpson’s mic was down at her side. Simpson tried to recover, dancing awkwardly before fleeing the stage. Simpson attempted comebacks, but never managed to recover from the humiliation of that infamous appearance.


Tonya Harding


Getty Images/Sport Classic/Tim DeFrisco


Figure skater Tonya Harding was a force to be reckoned with in the skating world during the late ‘80s and early ‘90s. In 1991, Harding became the first American, and second ever act, to complete the triple axel. Harding was then placed fourth in the 1992 Winter Olympics. On January 6th, 1994, one day before the U.S Figure Skating Championship Ladies’ Singles competition, Harding’s biggest competitor, Nancy Kerrigan was attacked after a practice session. It was revealed later that year that Harding’s then-husband, Jeff Gillooly, orchestrated the attack. Harding later pleaded guilty to hindering the prosecution and was banned for life from the U.S. Figure Skating Association.



Katherine Heigl


Getty Images/Entertainment/Peter Kramer


In 2007, Katherine Heigl was the actress to follow in Hollywood! She starred in the ABC medical drama Grey’s Anatomy and was even awarded an Emmy. However, the following year, Heigl publicly opted out of the Emmy race, saying: “I did not feel I was given the material this season to warrant an Emmy nomination… I withdrew my name from contention.” After bashing the hit show it was hard for Heigl to achieve the same level of fame, and gained a negative reputation. This just goes to show you can’t have your cake and eat it too.


Ryan Phillippe


Getty Images/Entertainment/Pascal Le Segretain


Ryan Phillippe rose to fame in the late ‘90s starring in box office hits such as I Know What You Did Last Summer and Cruel Intentions. His success continued in the early ‘00s, and was boosted by his high-profile relationship with actress, Reese Witherspoon. However, in 2007 rumors started swirling that Phillippe cheated on Witherspoon with his Stop-Loss co-star, Abbie Cornish. The rumors seemed to have been verified later that year when Witherspoon and Phillippe announced their divorce, and when in that same year, Phillippe and Cornish started dating. Following the divorce and cheating rumors, Phillippe’s career never really recovered.



Sinead O’Connor


Getty Images/ Entertainment/ Daniel Pierce Wright


Sinead O’Connor rose to fame in 1990 when she released a new arrangement for Prince’s song Nothing Compares 2 U. Following her success, O’Connor was booked as the musical guest on Saturday Night Live. During a performance of Bob Marley’s War, O’Connor tore up a picture of Pope John Paul II. Following the act, O’Connor was banned from SNL and her career took a major dive. O’Connor was heavily criticized by the public and at a New York rally piles of her records, tapes, and CDs were crushed by a steamroller.


Charlie Sheen


Getty Images/ Entertainment/ David M. Benett


Once the highest-paid actor on television, Charlie Sheen didn’t need much time to end his career. After making derogatory comments about Two and a Half Men creator, Chuck Lorre, Sheen’s contract with the show was terminated. Sheen then had an interview on 20/20, which appeared to be a meltdown. Seen insisted he was “winning” and had tiger blood in his veins. It seems that picking a fight with the boss that turned you into a household name and helped you make $1.8 million per episode, didn’t turn out well for Charlie Sheen.



Isaiah Washington


Getty Images/ Entertainment/ Vallery Jean


Isaiah Washington received worldwide recognition playing Dr. Preston Burke on the hit medical drama, Grey’s Anatomy. However, his choice of words led to his career downfall. According to many reports, including The Washington Post, Washington was “asked not to return”, a.k.a fired, after using a homophobic slur in reference to co-star T.R. Knight, while having an argument with another co-star, Patrick Dempsy. He then reportedly repeated the slur backstage at The Golden Globes. We don’t if Washington can salvage his career, but his return to Grey’s Anatomy for a single episode in 2014 is definitely a step in the right direction.


Lindsay Lohan


Getty Images/ Entertainment/ Stephen Lovekin


Lindsay Lohan was America’s sweetheart and starred in films such as The Parent Trap and Freaky Friday. However, Lohan’s career went down in flames following her multiple run-ins with the law. Lohan wasn’t helping her career when she started receiving a reputation of an actress that is hard to work with as her partying ways interrupted her work. By 2011, Lohan was sent to jail twice more for stealing a necklace and for failing to attend court-ordered classes. When Lohan borrowed money from another member of this “elite” club, Charlie Sheen, in 2013, it was sort of a confirmation Lohan really hit rock bottom.



Jamie Lynn Spears


Getty Images/ FilmMagic/ Michael Loccisano


Jamie Lynn Spears managed to do the seemingly impossible and make a name for herself outside her sister’s spotlight. At the age of 14, Spears starred as Zoey Brooks in the Nickelodeon show Zoey 101, and it seemed she had a bright future ahead of her in the acting and singing industry. However, in 2007, at the age of 16, Jamie Lynn Spears announced she was pregnant. Spears’ entire image was shattered, just like her career.




Getty Images/ WireImage/ Prince Williams


It seemed like B.o.B had a bright future in the rap industry with his 2010 hit Airplanes and his feature in the Jessie J 2011 hit Price Tag. However, B.o.B didn’t use his momentum and chose to stay low, which was mistake number one. Mistake number two was the one that truly destroyed his career. In 2016, the rapper tweeted that the Earth is flat. The rapper tweeted that if the earth were round that it would be obvious just by looking at the horizon. He went on a long rant, with one of the tweets reading: “The cities in the background are approx. 16 miles apart… where is the curve?” Maybe flying an airplane instead of singing about it could have helped this…



Dani Mathers


Getty Images/ Entertainment/ Frederick M. Brown


As far as Playboy models go, Dani Mathers had a skyrocketing career when she became Playmate of the Year in 2015. Mathers who may be used to comments on her appearance, learned the hard way that other people aren’t. When Mathers went for a routine gym session at LA Fitness, she posted a photo to Snapchat of an undressed 70-year old woman in the background. If you think that’s bad, the caption read: “If I can’t unsee this then you can’t either.” Mathers was called out for body shaming and had a misdemeanor filed against her. Her membership to the gym was revoked and lost all her modeling contracts.


Taylor Lautner


Getty Images/ Entertainment/ Sam Wasson


The Twilight franchise made Taylor Lautner a house-hold name and very famous. When the saga was about to be over, there was a huge interest in what the actors were going to do next. Usually, it is very important for actors that come out of a very recognizable role to choose their next role carefully in order to gain respect and appear as diverse actors. Unfortunately for Taylor Lautner, he made a wrong choice that cut his career short. Lautner went to star in the film Abduction, which was supposed to mark him as the next big action actor, but failed to do so. Instead, it marked Lautner as a one-hit-wonder and cost him his career.



Azealia Banks


Getty Images/ FilmMagic/ D Dipasupil


Initially, Azealia Banks had everything it took to become a rap icon. Banks was introduced to the mainstream with the release of her song 212 in 2011. Soon after, Banks embarked on what led to her eventual downfall: Twitter rants. Banks initiated feuds and stirred controversies. In 2013, for example, she called Rita Ora “thirsty” and a “Rihanna understudy”, and that is calm compared to her other tweets. If people care more about your tweets and feuds than your music, it means your career is pretty much over.