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 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

13 Chris Brown - Felony Assault

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

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

9 Emily Browning - Choosing to 'Rest' Over Work

8 Jennifer Grey - Identity Changing Plastic Surgery

7 Matthew Broderick - Breaking Bad

6 Sean Connery - Bobbits? Hobbits?

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

4 Mel Gibson - Racist Drunken Rant

3 Tara Reid - Plastic Surgery & Excessive Partying

via nydailynews.com

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

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.

More in Entertainment