Oprah and her producers have been looking back at their most memorable show moments—but Oprah says it's time to come clean about one huge oversight. "It is my duty to set things right," Oprah says.
On April 14, 2011, The Oprah Show bestowed its Laugh Out Loud (Lolly) award for the funniest moment in show history. "That night I got a frantic call from Gayle King, who has watched every Oprah Show since we started 25 years ago. She said there had been a terrible miscarriage of justice," Oprah says. "I think she might have been correct because she said, 'You forgot to include one of the all-time funniest moments.'"
That moment was the “goth mom makeover“ prank. Mastermind Jamie Kennedy posed as an off-the-wall stylist who turned a mom named Sue into a leather-clad, black-lipsticked wonder. "How could we have forgotten this?" Oprah says.
Though Sue got a real makeover after Jamie's prank, Oprah has asked Sue back to the show to make things right. "I want to right an egregious wrong and present you with our honorary Oprah Show Lolly Award titled 'OMG Oh My Goth,'" Oprah says.
Sue thanks Oprah and says she's still recognized from that show. "It's been amazing," Sue says. "My husband and I worked in Kuwait for four and a half years and people would call me in Kuwait and say, 'I was watching Oprah last night. By any chance were you ever in a makeover show?'"
The Oprah Show has booked nearly 30,000 guests, but none as high maintenance as one Hollywood icon. "Oprah loves The Wizard of Oz," producer Kristin Graham says. "It's one of her favorite movies, and it was my job to make sure that the ruby red slippers would get from the Smithsonian to Chicago."
Only the museum's curator is allowed to touch the very slippers Judy Garland wore in the film. Kristin says the 70-year-old slippers were carefully packed in a box of foam for the journey...but that wasn't the only travel accommodation they required. "It is the requirement of the Smithsonian that they have to fly first class," she says. "Not only did they fly first class with us, they had their own ticket."
In 25 years, The Oprah Show has pulled off feats never tried before on television. Still, Oprah says there are some shows she has been hesitant about. "I am not always thrilled about some of the crazy ideas that these guys come up with. Like the time they had me play a famous game show," Oprah says of her producers. "See, I really don't like games other than Scrabble. But I did it because they wanted me to."
In 2007, Deal or No Deal was the hottest show on television. Host Howie Mandel brought the entire game to Oprah's stage, and Oprah was playing on behalf of an audience member who would receive the money Oprah won.
Right off the bat, Oprah eliminated the case with the highest dollar amount. At the end of the game, she was left with two cases containing $5,000 and $75,000—and in the end, walked away with the $5,000 case. "It felt like a stomach-churning roller coaster ride, and I was hanging on by a thread," Oprah says.
Senior producer Julie Simpson was the brains behind that operation. As the game came down to the final two briefcases, Julie says the control room was pacing. "We've done some really serious, tense, intense shows—but nothing like that," she says. "None of us could sit down. I mean, we were pacing. Nobody was where they were supposed to be. We were sweating through our clothes."
The Harpo team is usually calm, cool and collected—but every so often even they have a "pinch me" moment.
Producer Kelly Rothschild Jansen's came when she was producing a show with Ricky Martin. "He was like the best looking guy I'd ever been around in my life," she says. "He was going to sing his new single featuring Joss Stone."
The night of rehearsal, Joss was running late. "[Ricky's] manager looks over at me and says, 'Kelly, can you be Joss?'" she says. "So I went up there onstage with Ricky Martin."
In 2009, Oprah and Gayle ventured into the Lone Star State to visit the State Fair of Texas—and producers realized they had bitten off way more than the best friends could literally chew. From fried guacamole to chicken-fried bacon, producers sent Oprah and Gayle on the ultimate food quest. "Gayle and I literally ate our way through that fair," Oprah says. "If it can fit in a fryer, it's at the Texas State Fair."
After their taste test, Oprah and Gayle retreated to a trailer to recover. "We felt really bad," producer Jenna Kostelnik says. "That was a lot of food."
After the fair, Oprah says she went to a friend's house. "When we walked in, they offered martinis and tequila shots," she says. "That is not a good mixture."
In October 2010, the halls of Harpo were alive with the sound of music. For the first time since The Sound of Music debuted in 1965, all of the actors playing members of the von Trapp family reunited on Oprah's stage.
Senior producer Julie Simpson and her co-producer Julie Rashid say they developed an unexpected crush on actor Christopher Plummer. "He's so charming, and he has this commanding presence," Julie S. says. "He's a bad boy, you know? He's got it."
Julie R. had the pleasure of greeting him. "When he walked in, he had these sunglasses on and this jacket," she says. "I was like, 'Well, oh, hello' and 'At 80 years old, you're like, oh my gosh.'"
Julie S. says Christopher flirted with the entire team. "We were butter," she says.
Even Oprah says she flirted back! "I would say he's very suave," she says. "Afterwards, he was like, 'Are you going to come to Canada and see me?' I was like, 'Tell me the day, I'll be there.'"
In November 2010, a two-day Oprah Show event featured 200 adult men who were molested coming forward to free themselves of their painful pasts and help others in the process. "It was one of the most groundbreaking and proud moments for me and everyone who works here," Oprah says.
For senior associate producer Ray Dotch, it was more than a show—it was a turning point in his life. Ray himself is a survivor. "When I first heard that my team was doing a show where the entire audience would be filled with men who were sexually abused, I thought, 'God, you've got to be kidding me,'" he says. "But almost immediately, I knew that it was something that I just needed to be a part of and that I needed to do, otherwise it wouldn't have come to me."
Ray says working on the show has changed his life. "It made it so that I don't carry the burden anymore. I am truly freed from it," Ray says. "This show is the best thing we've ever done because we gave men their lives back."
Ray also says the outpouring of support from within Harpo's walls and throughout the country has been overwhelming. "I've been stopped in the grocery store and at the gym and so many different places where people walk up and tell me their story and also say out loud that it happened to them—which means that the show lifted the shame, which was the point," he says. "Ironically, our team is being honored by the television academy for that episode, and the ceremony is on my birthday. It's like this is the way it's supposed to happen."