14 Of The Biggest Career Mistakes Celebrities Have Ever Made

As a celebrity, any mistake can be detrimental to one's career. That's exactly why celebrities have managers, agents, publicists, lawyers, assistants, personal accountants and entire entourages to ens

As a celebrity, any mistake can be detrimental to one's career. That's exactly why celebrities have managers, agents, publicists, lawyers, assistants, personal accountants and entire entourages to ensure they don't mess anything up. A single misstep or poor decision can end their career, turning a 'Hollywood star' into a 'Hollywood has-been'. Although celebrities can bounce back, miscalculated decisions can end up costing them millions of dollars. Here are fourteen of the biggest career mistakes celebrities have ever made.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

14 DMX - Drugs, Guns and Impersonating a Federal Agent

DMX is considered one of the best rappers of all time. He put out five platinum selling records between 1998 and 2003, and was also featured on the records of many other recording artists. DMX even had a budding acting career, starring in films like Cradle to the Grave, Belly and Exit Wounds. However, as his career began to flourish, it also began to perish, due to his legal issues. Drugs and numerous arrests came into play, which tarnished DMX's reputation. He has been arrested for animal cruelty, reckless driving, drug possession and identity falsification - among many other offenses. A crime he committed back in 2004, when he entered an airport with cocaine and a gun, while identifying himself as a federal agent was the tipping point for DMX. Although DMX has released two albums since then, neither album came close to the success of his previous albums.

13 Chris Brown - Felony Assault

Chris Brown was at the height of his career in 2009. He had two multi-platinum selling albums under his belt, several number one singles and he was dating R&B princess, Rihanna. An argument that escalated into a physical altercation on the night of February 8, 2009, between Chris and then girlfriend, Rihanna changed everything for the young star. He was charged with felony assault and making criminal threats. Following his arrest, Brown's music was withdrawn from multiple radio stations and advertisements featuring Chris were suspended. Since then, Chris has had a slew of legal troubles and his albums Grafitti (2009), F.A.M.E. (2011) and Fortune (2012) never reached platinum status.

12 Amanda Bynes - Twitter & Legal Issues

Prior to 2013, Amanda Bynes had a hot career starring in popular films like, She's the Man, What a Girl Wants and Hairspray. However, her life began to quickly unravel. The bizarre behavior began with a string of tweets in which Bynes talked about wanting plastic surgery, her hatred for the tabloids and her changing appearance. She also started several twitter fights with celebrities, which usually began by her calling them 'ugly'. In addition, Amanda had several legal issues including, possession of marijuana, driving under the influence and reckless endangerment. In July of 2013, Bynes set her neighbor's driveway on fire and almost set her dog on fire. Amanda was detained by police and sent to a mental facility, where she stayed for five months. She is now enrolled at the Fashion Institute of Design & Merchandising, but no career comeback is in the works at this time.

11 Charlie Sheen - Insulting Your Boss

Charlie Sheen was the king of television until early 2011. He was the star of the hit television show, Two and a Half Men and he was the highest paid actor on TV, earning $1.8 million per episode. On February 24th, 2011, Charlie made several anti-Semitic comments about his boss, Chuck Lorre, while being interviewed by the Alex Jones Show. Two weeks later, CBS fired Charlie Sheen from the hit television sitcom. Sheen went on to star in the TV series, Anger Management, but the show was cancelled after just two seasons.

10 Molly Ringwald - Biting the Hand That Feeds You & Turning Down Iconic Roles

Molly Ringwald is considered one of the greatest teen stars of all time and is widely known for her roles in the 80's films, The Breakfast Club, Sixteen Candles and Pretty in Pink. Her success is mostly credited to director, producer and writer, John Hughes, who cast Ringwald in her most prominent roles. Hughes wanted Molly to star in his 1987 film, Some Kind of Wonderful, but she turned it down, because she wanted to take on more adult roles. Hughes took the decision personally and as a result, the two had a falling out. Ringwald was then offered the role of Vivian, in Pretty Woman, but turned it down because she felt uncomfortable with the content of the script. Molly also turned down the lead role in the film Ghost, because she didn't believe in the script. Ringwald has only down cameos since the 1990's and played the mother in the ABC Family's television series, The Secret Life of the American Teenager, from 2008 to 2013.

9 Emily Browning - Choosing to 'Rest' Over Work

Emily Browning starred in films like The Uninvited, Sucker Punch and Lemony Snicket's a Series of Unfortunate Events. In 2008, the young actress turned down the role of Bella in the film, Twilight. Browning had just finished shooting The Uninvited and decided she was too exhausted to take on another film and wanted to take a break. The role went to Kristen Stewart, who is now a household name and has had an extremely successful career thus far. Emily Browning has yet to achieve that same amount of success.

8 Jennifer Grey - Identity Changing Plastic Surgery

Jennifer Grey became an instant Hollywood star in 1987, when she played the role of Frances "Baby" Houseman in the classic film, Dirty Dancing. The film was a huge hit and was the first film to sell one million copies on video. Jennifer's career ended as quickly as it started, after she underwent two Rhinoplasty procedures in the early 90s. The change in appearance, which made the star unrecognizable, destroyed her career. Grey spoke of the experience stating, "I went in the operating room a celebrity - and came out anonymous."

7 Matthew Broderick - Breaking Bad

Matthew Broderick is known for his roles in Ferris Bueller's Day Off, Glory and Inspector Gadget. In 2008, Broderick was offered the role of Walter White in Breaking Bad. Matthew turned down the role for an unknown reason. Breaking Bad is considered one of the greatest American television series of all time and in 2014, Breaking Bad entered the Guinness Book of World Records as the highest rated show of all time. The role of Walter White went to Bryan Cranston, who won three consecutive Primetime Emmy Awards for Outstanding Lead Actor in a Drama Series. Broderick hasn't had a hit movie since, The Producers, in 2005.

6 Sean Connery - Bobbits? Hobbits?

Sean Connery was offered the role of Gandalf in Peter Jackson's adaptation of Tolkien's Lord of the Rings trilogy, but turned it down. Connery's reasoning was that he didn't understand the script stating, "I had never read Tolkien and I did not understand the script when they sent it to me. Bobbits? Hobbits?” Producers tried to convince Sean to take the role, by offering Connery $10 million per film and 15% of the box office total for all three movies. Sean Connery has stated his regrets about his decision, after realizing that between his salary and his 15% stake, he would have earned $480 million. Don't cry for Sean, he's still worth an estimated $120 million.

5 Lindsay Lohan - Rehab and Saying 'No' to The Hangover

Lindsay Lohan has destroyed her career in more ways than one. The numerous arrests, stints in rehabs and a terrible work ethic has turned this A-lister into a D-list celebrity. However, in 2009, she was offered the role of stripper Jade in The Hangover, but turned it down, because she didn't like the script and thought it had no potential. The Hangover went on to become the second highest grossing R-rated comedy of all time and has spawned two extremely successful sequels.

4 Mel Gibson - Racist Drunken Rant

Mel Gibson was once considered an A-lister and one of the biggest action stars in the world, but a 2006 drunk driving arrest in Malibu, California changed all of that. The tapes from the arrest which included a tirade of anti-Semitic remarks from the Hollywood actor hit the media shortly after the arrest. The harmful and vile words resulted in Hollywood quietly blacklisting the once A-list actor. In 2010, he returned to the big screen with a lead role in Edge of Darkness, but the film bombed in comparison to Gibson's previous films. It had a budget of $80 million and earned $81 million in the box office, barely recuperating its expenses.

3 Tara Reid - Plastic Surgery & Excessive Partying


In the late 90s and early 2000s, Tara Reid was well on her way to becoming America's sweetheart with roles in films like, American Pie, My Bosses Daughter and American Pie 2. However, Reid was making headlines for her excessive partying, rather than her career which tarnished her 'sweetheart' image. In 2004, Tara underwent plastic surgery and received breast implants and liposuction on her abdomen. The surgery was so botched that it left her with several deformities. Between the partying, the botched surgery and a string of bad movies, Reid's career perished.

2 Paula Deen - Racist Remarks

Paula Deen, an American chef and cooking show host lost it all after a set of court documents were made public. The documents revealed Deen's testimony, where she openly admitted to using the N-word multiple times. Paula Deen found herself in the middle of a racism scandal, in which no amount of apologies could remedy the situation. The Food Network fired Paula Deen, ending her shows, Paula's Home Cooking and Paula's Best Dishes. Paula lost nearly all of her endorsement deals and her racist remarks cost her over $17 million.

1 Remy Ma - Attempted Murder

Remy Ma was the first female rapper of the Terror Squad, which included artists Fat Joe and Cuban Link. Ma was featured on the hit song 'Lean Back' and in 2006, the Grammy-nominated artist was on her way to the top. She had a growing fan base, an album that was selling well and her rap skills were widely acknowledged and appreciated. In July 2007, Remy was charged with attempted murder, assault and criminal weapon possession, after she shot a woman, who she believed stole three thousand dollars from her. Remy Ma was sentenced to eight years in prison and will not be released until 2015.

Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Entertainment

14 Of The Biggest Career Mistakes Celebrities Have Ever Made