10 of Diane Sawyer's Craziest Celebrity Interviews: Whitney Houston, Michael Jackson and More

Diane Sawyer received health advice from Dr. Mehmet Oz when he appeared as a guest on Good Morning America in 2009. She found herself in an awkward position when the celebrity doctor asked her to get out of her chair and do an exercise.

The American broadcaster — who was wearing a skirt then — followed Dr. Oz and spread her legs.

Brad Pitt had a sit-down interview with Sawyer where he promoted his film Mr. & Mrs. Smith. The interviewer asked him personal questions after branding Angelina Jolie a "homewrecker," as she pressed him on whether or not it led to his divorce from Jennifer Aniston.

"I'm a 41-year-old man, and I don't see any need to defend myself," the Ocean's Eleven star said.

Fans slammed Sawyer after her 2004 interview with Aniston, during which she asked her cruel questions about Nancy Dow. The Friends actress got emotional at one point, but it did not stop Sawyer from bombarding her with more queries.

Sawyer also showed photos Aniston had never seen before — as well as her mother's book she previously refused to see.

"Oh my god, where did you get that?" Aniston asked Sawyer, almost whispering. "Jesus. I've never looked at it."

Over 60 million people watched Sawyer's chat with Michael Jackson as it served as his first-ever interview since the child molestation accusations emerged. The interviewer questioned him over the allegations, particularly the sleepovers he had with kids.

"You'll have a child sleeping over…" Sawyer awkwardly asked, while the "Smooth Criminal" singer responded, "Of course. If they want. It's on the level of purity and love and just innocence, complete innocence. If you're talking about s--, then that's a nut, that's not me. Go to the guy down the street because it's not Michael Jackson."

In 2001, Janet Jackson appeared in the Primetime Live interview with Sawyer, where she faced questionable statements from the journalist.

Sawyer infamously asked her about "Would You Mind" lyrics and uncomfortably read the lines aloud — but things got worse when they started speaking about racism.

"Do you think I am incapable of understanding what it is?" she inquired.

Jackson then replied, "Yes, because you're on the other side."

Lisa Marie Presley spoke with Sawyer in 2003, setting the record straight about the reason why she married the late King of Pop.

Despite dodging the question, Sawyer still pressed further and spoke about the "romantic nights" the former couple had.

"I wasn't gonna get married if it wasn't that but see then it was like, wanting to get married," Presley answered. "So I don't know it if was, you know, like I even remember thinking how is that gonna happen. I can't even imagine him like that."

When Presley tried to change the question, Sawyer still replied, "What about him and drugs?"

Sawyer interviewed Mel Gibson about filming The Passion of the Christ amid the accusations he was an anti-Semite. Halfway through the interview, she asked him about the 2006 arrest and whether substances like alcohol and drugs had something to do with it.

"But you talked about the fact that you went on benders, got into fights," she said, citing people who said he consumed five pints before work.

Gibson's fans commented on the interview and slammed Sawyer for her unimpressive questions.

One said, "It is amazing how Diane's questions are so so dumb or silly."

"In this interview, Diane Sawyer embodies everything we hate about 'journalists,'" another fan wrote.

In a 20/20 interview, Sawyer pushed Rihanna, even though she told the journalist she felt embarrassed and humiliated to see the photos of the injuries she sustained when Chris Brown assaulted her.

"Why be shamed? Why would you be ashamed?" Sawyer asked.

"I fell in love with that person," the "Umbrella" singer said. "That's embarrassing."

Rihanna's supporters called out Sawyer and her victim-shaming tactics that left the artist embarrassed and uncomfortable.

"Dianne Sawyer is the most exploitative journalist I know. Seeing if she wanted to look at the picture that's obviously painful, reading the police report; I just can't believe her sometimes," one said.

In a rare interview with Sawyer a decade before her death, Whitney Houston broke her silence about the rumors claiming she was sick. The 77-year-old broadcast journalist asked her whether her gaunt appearance was caused by anorexia, bulimia or drugs.

"First of all, let's get one thing straight. Crack is cheap," she told Sawyer after her persistent queries. "I make too much money to ever smoke crack. Let's get that straight. OK? We don't do crack. We don't do that. Crack is whack."

In Sawyer's 2003 ABC primetime interview with Britney Spears, she spoke about Kendel Ehrlich — the wife of Maryland's then-governor Robert Ehrlich — who said she would shoot the "Toxic" singer if she had an opportunity to do so.

"Because of the examples for kids and how hard it is to be a parent and keep all of this away from your kids," Sawyer said, leading fans to accuse her of defending Kendel.

"It's one thing to not want to be the role model anymore," Britney continued. "It's another thing not to know that a lot of young girls are looking at this…a lot of them."

Elsewhere in the interview, Sawyer also accused Spears of causing Justin Timberlake "so much pain" and "so much suffering" that she reportedly caused the breakup.