Michael Jackson, 1993
After 14 years of refusing to talk to journalists, the King of Pop finally agreed to a sit-down interview with Oprah in 1993 - almost a decade before he would similarly welcome Martin Bashir into his Neverland home. Throughout the 1980s, more and more rumours around Jackson’s changing appearance and strange behaviour had emerged in the press, so it was truly sensational at the time to see the chat show host grilling him on everything from plastic surgery rumours to the reasons behind his obsession with childhood. He candidly shared his experiences of growing up in the spotlight, the loss of his own childhood and his abuse at the hands of his father, Joe Jackson.
Ellen DeGeneres, 1997
After years of hiding her sexuality, actress Ellen DeGeneres came out via an episode of her wildly successful sitcom, Ellen, in which her character Ellen Morgan tells Laura Dern’s Susan that she is gay (Oprah even had a cameo in the episode as her therapist). On the same day that ‘The Puppy Episode’ aired, she sat down to a tell-all interview with Oprah, one that reportedly garnered the most hate mail the chat show host has ever received. In the interview, she discussed why she decided to make her character come out, and why she had made the decision to stop hiding the truth after so long.
Tom Cruise, 2005
One of the most imitated pop cultural moments of the 2000s, Tom Cruise jumping up and down on Oprah’s sofa while shouting ‘I love her’ about new girlfriend Katie Holmes will undoubtedly go down in television history as one of the strangest celebrity interviews. Ostensibly on the show to promote his new film War of the Worlds, the interview should have been the kind of hum-drum PR-trained routine that we are used to seeing from A-list celebrities, but instead Cruise waxed lyrical about Holmes, gaining enthusiasm until that climactic sofa-bounce.
Rihanna, 2012
When pictures emerged of pop star Rihanna’s bruised face after her then boyfriend Chris Brown assaulted her in 2009, she was reluctant to discuss what had happened in public. Just three years later, she agreed to sit down with Oprah, surprising the world with her forgiveness for her ex. She described how the two had worked on becoming good friends again, and that she was now at peace with what had happened to her. She opened up about her childhood and repairing her relationship with her father, too, and was visibly moved throughout.
Lance Armstrong, 2013
His fall from grace was truly Icarus-like in scale, so when shamed athlete Lance Armstrong agreed to confess to his doping crimes on Oprah, the world waited with baited breath. The chat show host did not hold back, asking him for all the details of his cheating in what felt like a courtroom cross-examination, as she asked him about what he took, when he took it, and why, as well as if it would have been possible to win seven Tour de France competitions without doping.
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