Most Infamous Celebrity Interviews

When Rihanna sits down tonight with Diane Sawyer on '20/20', it's sure to be one of the biggest interviews of the year. But will it go down as one of the biggest interviews of all time? Over the years, the celebrity interview has become one of the staples of the entertainment industry. Make a huge mistake? Go on the 'Tonight Show' and humbly plead forgiveness. In need of a reputation makeover? Talk to Oprah and shed a tear. Need to generate instant headlines? Letterman is your man. When celebrities open up, crazy things seem to follow, so whatever happens tonight, chances are people will be talking about it tomorrow. In order to help Rihanna prepare, then, we thought we'd give her (and you) a refresher course in some of the most infamous interviews of all time.

Of course, Rihanna isn't doing an interview to rehab her image; that task was left to her rightly vilified ex Chris Brown, who appeared on 'Larry King Live' with both repentance and a bow-tie ensemble he borrowed from Archie Andrews.



Tom Cruise has had so many crazy interviews in recent years that it was difficult to narrow it down to just one. But while his appearance on 'Today' is legendary, it was prompted by the need to explain his antics on 'Oprah Winfrey'. So by default, the couch episode trumps all.



Perhaps the most famous act of celebrity contrition came back in 1995 when Hugh Grant, fresh off his prostitution scandal, appeared with Jay Leno, who spoke for America when he asked "What the hell were you thinking?"




Whitney Houston makes her first appearance on our list thanks to her infamous 2002 talk with Diane Sawyer, which immortalized the phrase "crack is whack". Truer words have never been spoken, Whitney.



It's not just movie and music stars that turn to the media in times of crisis. One of the most famous interviews in television history took place in 1992, when presidential candidate Bill Clinton appeared on '60 Minutes' to emphatically deny reports of infidelity. Hmm.



Perhaps more than any other celebrity, Farrah Fawcett lived her life in the spotlight, opening up to cameras about every detail of her life, even the iffy parts. She vaulted back into the spotlight in 1997 thanks to a wacked out interview with David Letterman.



1993 was an up and down year for pop legend Michael Jackson. He started off strong, appearing in this full length special with Oprah Winfrey, which briefly rekindled interest in his career. The effect was undermined, however, by the child molestation charges that followed later that summer.



Britney Spears has had enough unwanted media attention in her life, so she probably didn't need to be grilled by Matt Lauer. Yet it was this exact topic that finally caused her to break down. Wow, that's pretty meta.



David Letterman has had more than his share of uncomfortable interviews, locking horns with everyone from Madonna to Joaquin Phoenix to Crispin Glover. Our favorite, though, is this complete dismantling of Paris Hilton, which was so thorough we actually started to feel bad for her.




Our trip through the annals of celebrity interviews wouldn't be complete without a return to Whitney Houston. Seven years after damaging her reputation almost beyond repair with her Diane Sawyer interview, Houston turned to a higher power to help rehabilitate it: Oprah Winfrey.