Riley Cooper

Scott Cunningham/Getty Images

Riley Cooper has apologized for his use of the N-word, calling his behavior "disgusting" and asking forgiveness from his NFL teammates, coaches and fans.

Unfortunately for the Philadelphia Eagle, oftentimes even the sincerest apology isn't enough to keep a racial scandal from permanently tarnishing your reputation. But Riley is far from the first celebrity whose comments on skin color have caused an upset.

In June 2013, Paula Deen admitted to having used the N-word in the past and begged for forgiveness on Today. "Inappropriate, hurtful language is totally, totally unacceptable," she said. "And I tell you what, if there's anyone out there that has never said somethin' that they wish they could take back, if you're out there, please pick up that stone and throw it so hard at my head that it kills me," she said through tears. "I want to meet you. I want to meet you. I is what I is, and I'm not changin.'"

Ultimately, however, her apology was not enough. The Food Network failed to renew her contract, and she lost several of her sponsors.

Paula Deen

Jamie McCarthy/WireImage

Big Brother season 15 contestants have paid the price for their insensitive commentary, too.

In July 2013, several of the housemates were overheard using racial slurs during a 24-hour live feed on CBS. The show even pulled together a montage of scenes of some of Aaryn Gryes' worst rants, including her telling fellow contestant Helen Kim she should "go make rice," adding, "I probably look like a squinty Asian right now." She was very quickly dropped by her modeling agency.

CBS explained in a statement that they do not "condone" the racial comments, adding that "Any views or opinions expressed in personal commentary by a houseguest appearing on Big Brother, either on any live feed from the House or during the broadcast, are those of the individual(s) speaking and do not represent the views or opinions of CBS or the producers of the program."

Even Hollywood's nicest guy isn't immune to involvement in racial controversy. A 2004 video of Tom Hanks emceeing an event at his children's school went public in March 2012, in which the actor shared a stage with a white man in blackface.

Hanks explained in a statement he was "blindsided when one of the parents got up on the stage that was hideously offensive then and is hideously offensive now," adding, "What is usually a night of food and drink for a good cause was, regrettably, marred by an appalling few moments."

Ashton Kutcher, Pop Chips Video

There's also Ashton Kutcher who, wearing brownface, parodied Bollywood in a May 2012 PopChips ad.

PopChips said in a statement the commercial "was created to provoke a few laughs and was never intended to stereotype or offend anyone." Ultimately, however, PopChips pulled the ad. As one commenter snarked, though, "The most offensive when Ashton Kutcher thought he was funny."

Back in 2006, a (usually) seriously funny guy, Seinfeld's Michael Richards, launched into a racist rant. During his performance at Los Angeles' Laugh Factory, he lashed out at hecklers in the audience, using the N-word multiple times. He apologized on The Late Show With David Letterman, saying he was "deeply, deeply sorry."

In September 2012, he reflected on the incident on Jerry Seinfeld's "Comedians Getting Coffee" webseries, saying: "I busted up after that event. It broke me down." He admitted he "took it too personally," saying, "I should have just said, 'Yeah, you're absolutely right. I'm not funny. I think I'll go home and work on my material and I'll see you tomorrow night.' And split, or something. Anything. But it's just one of those nights."

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