Everyone had a celebrity crush as a teenager—including Oprah. "I remember seeing the Jackson 5 and thinking, 'Oh gee, I'd like to marry Jackie Jackson,'" she says. "He was my favorite of the Jackson 5."

Excutive producer Sheri has assigned Leslie's team to take a trip through the way-back machine for their next show—teen heartthrob surprises! "The reason why we want to do the teen heartthrob show [is] it's all about Jackie Jackson and surprising Oprah," Sheri says. "It's that nostalgic feeling of you were once a teenage girl and here's who you were in love with and here they are today. It's just fun."

After masterminding the Judds surprise that moved Oprah to tears, Leslie has another trick up her sleeve for Oprah. "Jackie really wants to take Oprah out on a date," she says. "There's a lot of moving parts to this show."

Jackie Jackson isn't the only surprise of the show. Leslie's team is also hard at work to pull off a shocker for one of the Backstreet Boys' biggest fans. "I put the team on a mission to find the biggest fan in America," she says.

The team found Noelle and will have something special waiting for her at the airport. "The girls are flying into O'Hare, the second busiest airport in the country," Leslie says. "The Backstreet Boys will be at the gate and they will sing one of their songs." 

To help her pull off the surprise, Leslie enlists the help of senior production assistant Gwen.

Watch Leslie brief Gwen. 

"I feel like Leslie's leaning on me a little bit more to make this happen," Gwen says. "So I'm a little nervous."

Gwen at airport

The next day at O'Hare Airport, Gwen and her team are in place to hatch their plan. Assistant producer Sarah will wait with the Backstreet Boys while Gwen grabs the girls right when they step into the Jetway. Pretending that Sarah is a driver, Gwen will call Sarah and ask her to bring the car around. When Sarah gets the call, she'll cue the group to start singing and give Noelle the shock of a lifetime.

As Sarah briefs the Backstreet Boys, Gwen notices her cell phone calls keep dropping. "One of my huge responsibilities in pulling off the surprise is to use my cell phone to cue when the Backstreet Boys should start singing," Gwen says. "I'm just getting more and more nervous."

With five minutes until Noelle's plane lands, the team gets the Backstreet Boys in place. When the plane is at the Jetway, Gwen dashes in. "Then I get on the Jetway, waiting for the girls, and my cell phone is dropping every call I make," she says. "I felt I was going to be the one because of my cell phone not making a call to ruin the entire surprise."

Backstreet Boys surprise

Finally, Gwen grabs the cameraman's phone and the surprise goes off without a hitch. "The look on the girls' faces when they walk through the Jetway and see the Backstreet Boys is priceless," Sarah says.

"I only remember little bits and pieces because there was so much excitement and nerves ," Gwen says. "It was a huge [surprise] to pull off, and I think it was amazing."

Catch up with the Backstreet Boys
Oprah preshow meeting

While Gwen is hard at work with the Backstreet Boys, Leslie and the rest of her team are back at Harpo trying to pull one more con on Oprah. Their plan is to surprise Oprah with Jackie during their preshow meeting, and Jackie's bound to arrive any minute. "I'm sitting in the meeting and I have to act as calm and cool as possible and still give Oprah information about the show," she says. 

Leslie starts running through the show guests with Oprah. When she gets to Jackie, Leslie is afraid she'll give the surprise away before Jackie walks in. "I thought for sure she might suspect," she says. "You can't even be frustrated at that point anymore because you're just, like, 'Well, whatever happens, happens. Whatever's going to go down is going to go down.' And you just have to, like, offer it up."

Leslie also has another challenge. "I'm stalling Oprah Winfrey, and she wants to get those meetings over," she says. "I don't even know if Jackie Jackson's ready to go or not."
Jackie Jackson and Oprah

Thankfully, Jackie's in the building and makes his entrance right on cue! 

Watch how the team pulled this off

When Oprah sees Jackie, the 13-year-old inside of her is unleashed. "When Jackie Jackson walked through that door, I don't think I've ever seen Oprah scream that loud," Leslie says. "I haven't seen that look on her face in a long time, so that was really, really fun."

Oprah is flustered. "Suddenly, your brain is going like this," she says. "So I had a deeper love than I knew when he showed up."

Jackie asks Oprah to dinner, and she nervously gets ready. "When Jackie says, 'Let's go across the street and get a bite', the first thing I said, 'Oh no, that's okay,'" she says. "Because I'm thinking, 'When's the last time I had to be a fun date?' A long time. Ask Stedman, he'll tell you."

Watch Oprah prepare for her date with Jackie Jackson

When Oprah's ready, Jackie picks her up outside her office and escorts her to dinner. "It was interesting because I was thinking, 'What would happen if I had married Jackie Jackson?'" she says. "I would have been Michael Jackson's sister-in-law. Little Janet would be coming to my house, we'd be cooking together. Who knows?"

Oprah and Sheri

The next morning, Oprah arrives for taping still giddy from her date with Jackie Jackson. She fills Sheri in on the night. "Stedman's in Bermuda golfing, so I talked to him last night. He goes, 'So, how's your day?'" Oprah says. "I go, 'Well, I had a date with Jackie Jackson.' He goes, 'Yeah, really? How's Sadie doing?'"

Watch part of Oprah's date with Jackie

Oprah says she appreciates how this show makes viewers feel. "This show, literally you're transported back to that part of yourself that was hopeful and believed that anything could happen," Oprah says.

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