Oprah is a female entrepreneur and mogul on the top of many role model lists, and for good reason. She’s experienced the American dream in full, earning millions as a producer, book club creator, talk show host, actress, and magazine publisher, not to mention being the host of the most successful daytime talk show of all time. From poverty and trauma to total icon, here are Oprah’s most controversial interviews of all time.
1. Elizabeth Taylor
When Oprah got an interview with Elizabeth Taylor, it was a big deal, but Winfrey committed one big no-no — she asked about the star’s romantic life. After asking, Taylor responded, “none of your business” and was rude for the rest of the interview, which was obviously filled with bad blood and hostility. Oprah even made a sarcastic quip about Taylor not opening up about anything, and Taylor called it “the worst interview of my life”.
2. Tom Cruise
Everyone remembers the couch-jumping incident — when A-lister Tom Cruise, who definitely knows the rules of talk show etiquette, admitted that she was super smitten with Katie Holmes, leading him to jump out of his seat, throw his arms in the air, fist-pump, get on one knee, slap the ground, and do a bunch of other crazy things. The crowd loves it, and while Oprah had a smile on her face, she was obviously shocked by the ordeal.
3. Michael Jackson
A M.J. Q&A was coveted for any journalist, and Winfrey jumped on the chance. It was the singer’s first public talk in 14 years, and he used it as a chance to address controversy and rumors. He explained that the reason for lightening skin was due to a genetic skin disease known as vitiligo. He also claimed that his friendships with children was due to his own lost childhood, which was spent working as a performer. He also opened up about abuse from his father.
4. Jay Leno
Even though Leno might seem like a friendly guy on screen, behind the scenes, he was a master manipulator climbing the career ladder. He had a rep as a villain of the late night shows and an instigator of a feud with Conan O’Brien. When he was invited on Oprah’s show to share his side of the story, he made a bunch of passive-aggressive excuses and admitted that his retirement announcement was a “white lie.” He didn’t do much to make himself look better, and in a poll after the interview, 96% of Oprah’s audience said they were on Conan’s side.
5. James Frey
No one can forget that interview where Oprah laid into her guest James Frey. In 2005, her pick for Oprah’s Book Club was A Million Little Pieces, a memoir from a man chronicling his brutal struggle with drug addiction. Although it became a non-fiction bestseller, a year later an exposé was released that he made up a large amount of the stories in his memoirs. He reappeared on her show, where an angry Oprah explained she felt “duped” and “betrayed”.
6. Terry McMillan
You might know Terry McMillan from her famous novel-turned-movie, How Stella Got Her Groove Back. She fell for a younger man, just like her protagonist. In 1995, 43-year-old Terry traveled to Jamaica and fell in love with a 20-year-old called Jonathon Plummer. The two married but split up in 2005 when he admitted that he was gay. A scandal and public fight ensued, and Oprah provided a platform for the writer to confront her ex. After the show, she sued Plummer for $40 million and won, but didn’t make him pay. Finally, they patched things up in 2010 — on Oprah!
7. Mackenzie Phillips
When this celebrity went on Oprah’s show, no one could have expected what would be revealed in the tell-all. Phillips went on the show to promote her memoir High on Arrival, and described that she was drugged by her father John Phillips of the Mamas and the Papas, who sexually assaulted her. She went on to reveal that the assault continued (along with a resulting drug addiction) for the next decade. The claims led to a fallout with her half-siblings, who were doubtful of the claims.
8. Lance Armstrong
Lance Armstrong used to be America’s hero and champion of perseverance — especially after he won the Tour de France, one of the world’s most exhausting bicycle race that lasts multiple weeks. He won it seven times — consecutively — even after a cancer diagnosis. Still, when he starred on Oprah Winfrey’s show in 2013, he revealed the truth that he took performance enhancing drugs for cycling and all his Tour de France wins, saying that he would spend his life trying to earn back the trust of his fans.
