20 Outrageous Oprah Moments

You’ve seen the car giveaway and the day she showed off her new figure, but what about the time she talked auto-eroticism with Gayle, praised Kate Winslet’s breasts, and rapped with Jay-Z?

You’ve seen the car giveaway and the day she showed off her new figure, but what about the time she talked auto-eroticism with Gayle, praised Kate Winslet’s breasts, and rapped with Jay-Z? Plus, reactions to Oprah's exit from Tina Brown, Kim Masters, and Lorraine Ali.

Deconstructing Kate Winslet

Last January, Oprah told Kate Winslet how she really felt about her. “I love the fact that you have real breasts,” she said, sparking a detailed discussion about the actress’ physique.

Everybody Gets a Chicken

Once upon a time, Oprah gave away DVD players and cars to her audience members. Then the recession hit, and the big-ticket items were downgraded to fried chicken and biscuits.

Ted Haggard's Sexual Confusion

Evangelical preacher Ted Haggard opened up to Oprah about being caught soliciting a male prostitute and buying crystal meth. He told the talk-show host that one spiritual leader had advised him to “be more busy at the church” while he tries to go straight.

Tom Cruise Flips Out

Where were you the day Tom Cruise lost his mind on national television? We know where we were—glued to the set watching Oprah. Somehow Oprah makes watching celebs melt down on camera feel less like tawdry voyeurism and more like finding your spirit.

Stephenie Meyer Emerges

Stephenie Meyer, the reclusive author of the Twilight juggernaut, only did one interview during the entire press junket for the movie adaptation of New Moon. The lure of Oprah was enough to get the camera-shy writer to dish on the dream that inspired the hit novel, and what’s next for the franchise.

Mackenzie Phillips' Incest Revelation

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In what is perhaps the most effective anti-drug PSA of all time, actress Mackenzie Phillips told Oprah that she and her father, musician John Phillips, engaged in a 10-year sexual relationship while under the influence.

Oprah’s First Tweet

Oprah entered the blogosphere not with a bang, but a whimper, as her first on-air tweet failed to post correctly. Still, her embrace of the technology helped legitimize it to housewives across the Heartland.

James Frey’s Rise and Fall

Oprah can make you or she can break you, and with James Frey, she did a little of both. When Oprah picked Frey’s memoir of drug addiction and recovery for her book club, sales went through the roof. Later, amid allegations that the author had fabricated large swaths of his story, Oprah sat him down for a devastating interview that cowed him and made him a punchline for years to come.

Oprah Loves the Snuggie, Alas

Endorsing Twitter or the Kindle is one thing. Endorsing the Snuggie—that’s just wrong, Oprah.

Whitney Houston’s Spats With Bobby

Let's just say it wasn't the greatest love of all. For the premiere of Oprah’s 24th season, Whitney Houston detailed how ex-husband Bobby Brown emotionally abused her and even spat in her face. Bobby later went on The Insider to give his side of the story.


Frank talk about sex is nothing new on Oprah, but this uncomfortable clip where the talk-show host’s longtime gal-pal Gayle King talks about panelist Mark Consuelos’ pubescent masturbatory habits got a bit too frank.

Michael Jackson’s Troubled Past

When the King of Pop died in June, it was hard not to recall this heartbreaking interview from 1993 where Jackson opened up about the abuse he’d suffered at the hands of his father.

Most Vapid Interview Ever?

Is this the most banal exchange in the history of television? Or is the fact that Oprah gets a laugh talking to this utterly uninspiring duo a testament to her genius? Two words: double toasted.

Sarah Palin Gets Mavericky

You’ve got to hand it to Oprah—her interviews have staying power. After vice-presidential also-ran Sarah Palin appeared on the show, the blogosphere and mainstream media couldn’t stop buzzing about her various talking points, from her jabs at Levi Johnston’s budding porn career to her one-sided feud with Katie Couric.

The Tyson-Holyfield Peace Summit

Twelve years after the ear-biting incident, Oprah reunited Mike Tyson and Evander Holyfield in a much more peaceful encounter. Shaking hands, Tyson praised his former foe as “a beautiful guy.”

Even When She Loses, She Wins

After passionately campaigning to bring the 2016 Olympics to Chicago, Oprah was forced to deal with an unfamiliar scenario: defeat. When she addressed the shocking loss to Rio on her show, she managed to do so with humor and charm, coming out on top as usual.

She’ll Make You a Star

The list of “star experts” Oprah has launched over the years is vast, from go-to shrink Dr. Phil to go-to interior decorator Nate Berkus. And let’s not forget her go-to internal-medicine specialist, Dr. Mehmet Oz, as seen in this (graphic) clip.

Dane Cook’s Mysterious Disappearance

We haven’t seen Dane Cook headline a movie since he mocked Oprah to her face. Coincidence?

A Good Cry

One of the keys to Oprah’s success has undoubtedly been her talent for eliciting tear-jerker responses from guests, as seen in this poignant exchange with Michael J. Fox, during which the actor explained that Parkinson’s disease “doesn’t define me.”

Oprah From the Block?

Oprah is many things to many people. But one thing she’s not is a freestyle rapper—despite Jay-Z’s best efforts to teach her. You can’t claim Miss O. isn’t a good sport.