12 Most Monumental Career Mistakes Celebs Have Ever Made

Let's face it, everyone makes mistakes - but when you're a celebrity those mistakes, no matter how minor or major they are, can completely destroy your career. Since celebs are constantly in the public eye, even mistakes that are made in their personal lives can have detrimental effects on their professional lives. This is why it's imperative that celebs have entire teams of agents, managers, assistants, publicists, lawyers, etc.. to ensure that mistakes are kept to a minimum. After all, one poor decision has the ability to turn an A-list star into a Z-list has-been (very quickly). Here are the 12 most monumental career mistakes celebs have ever made.


12 Chris Brown – Felony Assault

With two multi-platinum selling albums, several number one singles, and R&B princess Rihanna as his girlfriend, Chris Brown was at the height of his career in 2009. An argument that escalated into a physical altercation on the night of February 8, 2009 between Chris and 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 Following his arrest, Brown’s music was withdrawn from multiple radio stations and advertisements. Since then, Chris has had a slew of legal troubles and his albums Graffiti (2009), F.A.M.E. (2011) and Fortune (2012) never reached platinum status.

11 Kanye West - Interrupting Taylor Swift


At the 2009 VMA's, Kanye West created one of the most infamous moments in award show history when he stormed the stage during Taylor Swift's acceptance speech for Best Female Video. He grabbed the mic from her and declared, "Yo, Taylor, I'm really happy for you and I'mma let you finish, but Beyoncé had one of the best videos of all time." Afterwards, Kanye was criticized for his actions by fans, celebrities, and even President Obama who called him a 'jackass'' and his tour with Lady Gaga was cancelled. Fast forward six years later, he was booed from the crowd throughout his own performance at the 2015 VMAs. Although, he is an extremely talented artist to this day his career has been defined by that moment.

10 Chris O'Donnell - A Titanic Mistake

Titanic is a classic, critically-acclaimed film and one of the most beloved love stories of all time. It's responsible for launching the careers of Leonardo DiCaprio and Kate Winslet, turning both of them into household names and cementing them as A-list stars. It's hard to picture anyone else playing the role of Jack, but Chris O'Donnell was originally offered the role. Chris turned down the role, opting for the role of Robin in the 1997 box office flop Batman & Robin. Although, Chris has had a somewhat steady career in the industry, his stardom in no way compares to Leo's.

9 John Mayer - TMI


In the early 2000's, John Mayer was well-known for his acoustic rock music that was both critically-acclaimed and commercially successful. With hits like 'Your Body is a Wonderland', 'Waiting on the World to Change', and 'Daughter's', Mayer seemed like a sensitive musician. However, that image was destroyed when he did an interview with Playboy Magazine in 2010 and revealed TMI about his sexual preferences and past relationships with Jessica Simpson and Jennifer Aniston. He revealed that sex with Simpson was "like sexual napalm" and when asked if black girls throw themselves at him, Mayer responded, "My d*ck is sort of like a white supremacist." His remarks were widely described as tactless and tasteless. Since the interview was released, the world hasn't heard much of John Mayer.

8 Jennifer Grey - 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 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.

6 Sarah Michelle Gellar - Clueless

Sarah Michelle Gellar was launched into pop culture fame with the role of Buffy in the hit TV series Buffy the Vampire Slayer, which aired from 1997-2003. Gellar has had great success with her television career, but has always struggled when it comes to landing great roles in film. Aside from her portrayal as Kathryn in Cruel Intentions, Gellar has starred in a number of box office flops and straight-to-DVD films. However, she was offered the lead role of Beverly Hills blonde Cher Horowitz in the 1995 film, Clueless. The actress had to turn down the role because filming conflicted with her schedule on All My Children. The part eventually went to Alicia Silverstone and ended up launching her career and making her a household name. Clueless went on to become a cult classic and is considered one of the best romantic comedies of all time. Perhaps, this is what Sarah Michelle Gellar needed to kick-start her film career.


5 Josh Hartnett Turned Down Superman

In the early 2000's, Josh Hartnett was Hollywood's "it" boy, starring in films like Black Hawk Down, Pearl Harbor and 30 Days of Night. However, these days his career isn't what it used to be and perhaps that had to do with a few decisions he made. After several box office hits, the offers were pouring in. Hartnett was offered the role of Spiderman, Batman and Superman, but he turned all of them down because he thought those types of roles would define his career. Then he decided to take 18 months off from Hollywood and go home and spend time with friends and family. When he returned, the offers weren't coming in anymore and he had become old news. Since his return to Hollywood, he's appeared in some indie films and he stars in the Showtime horror series Penny Dreadful - but his star power and film career isn't what it used to be.

4 OJ Simpson - Trial

Despite the fact that O.J. Simpson was acquitted of the 1994 murders of ex-wife, Nicole Simpson and Ronald Goldman, his career was destroyed in the process and has never recovered. The courts may have found him innocent, but in the public's eye he was guilty. Simpson is currently serving a 33-year prison sentence for crimes he committed in 2007 which included armed robbery and kidnapping - so it doesn't look like he'll be having a career comeback anytime soon.

3 Bill Cosby - Sexual Assault Allegations


Bill Cosby was once one of the most beloved actors in Hollywood; however, a slew of sexual assault allegations from more than fifty different women has sent his career into a downward spiral and effectively destroyed his reputation. Although, the accusations started in the early 2000's, the turning point wasn't until 2014 when comedian Hannibal Buress called Cosby a r*pist during one of his stand up routines. After the clip went viral and many more women came forward, TV Land pulled reruns of The Cosby Show from the air, Netflix cancelled Cosby's comedy special and NBC cancelled Cosby's upcoming sitcom.

2 Justin Bieber - Acting Like a D-Bag

Justin Bieber came on the scene in 2010 with his debut album, My World 2.0, which boasted several number one singles and went 3x platinum. With a huge fan base of Beliebers, his next three albums were hits as well. However, his career and popularity has taken a hit recently followed by years of bad behavior, bratty antics, and acting like a total d-bag. From vandalism and reckless driving to fighting with fans and paparazzi to using the 'N' word, the public seems to be fed up with this spoiled and disrespectful pop star. His management team launched a PR campaign last year to try to repair Bieber's reputation and career. This included an appearance on Ellen, a lighthearted Comedy Central Roast, and a heartfelt apology on YouTube. Time will tell if these efforts to re-brand himself as a decent human being work.

1 Jamie Lynn Spears - Teen Pregnancy


From 2005 t0 2008, Jamie Lynn Spears starred on the Nickelodeon teen sitcom, Zoey 101. Jamie, sister of pop princess, Britney Spears had the whole world at her feet and a promising career ahead of her. Following in her sister's footsteps, she even sang the show's theme song 'Follow Me.' However, in 2007, at the age of sixteen, Jamie announced that she was pregnant and Zoey 101 was cancelled shortly after. In 2013, she attempted to relaunch her career as a country music artist, but her album barely cracked the Billboard 200 list.


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