How Tom Cruise’s Olympics Stunt Was Inspired by… Conan O’Brien

Ben Winston might soon lose count of how many times he’s sent Tom Cruise up in the air.

Previously, the pair worked to get James Corden in aloft to go skydiving and then again to co-pilot a fighter jet on The Late Late Show. During Sunday night’s LA28 segment of the Paris Olympics‘ Closing Ceremony, Winston had the stunt-loving Mission Impossible star jump off the Stade du France in real-time and revealed the fruits of the year-and-a-half-long collaboration with the pre-taped shot of him skydiving with the Olympic flag over the hills of Southern California.

The original plan was for a balaclava-clad stunt person to do most of the heavy lifting, but Cruise would have none of it. “I don’t think there’s anybody like him in the world,” says Winston, who served as creative director and executive producer under the Fulwell 73 Productions banner. “There is no better collaborator.”

Speaking the afternoon after the live Paris jump and the starry beachside concert featuring The Red Hot Chili Peppers, Billie Eilish, Snoop Dogg and Dr. Dre, Winston revealed how he and Cruise kept most of their plan under wraps for as long as they did, what changed in the planning and the unlikely roots of the Olympic flag’s pre-taped journey from France to the U.S.

Are you just a glutton for logistics?

It feels a little bit like having a baby. You’re up all night, it’s all really stressful and you’re changing nappies, and they’re sick on you. Then, when they get to three years old, you’re like, “Oh, they’re so cute and lovely. I think I want another one.” You forget what a nightmare it was. I feel like live television might be that. You forget how much you go through.

Plenty has been revealed and speculated about in the wake of this stunt. How long have you actually been working on this? 

My first meeting was January 2022 when I sat down with Casey Wasserman at LA28. I haven’t been working on it since then, but I had the idea more like 20 months ago when they’d told me there’s this tradition of a 12-minute show that the next nation does in the closing ceremony. Within the first five minutes, I was like, “Well, it would be the coolest thing if we snatched the flag, and we could get Tom Cruise to do it.”

In multiple countries, no less.

I’ve seen lots of handovers where the country that takes over does something in the stadium, and they’ve been great, but I wanted to do something different. I like to be able to control everything. So I was thinking if we did it in Los Angeles, I’d be able to control all the elements a little bit more. I liked the idea of doing the bulk of it in Los Angeles but with an amazing open in Paris. This is such a weird reference, but remember when Conan O’Brien started on The Tonight Show and moved from New York to Los Angeles? He did a really fun sketch going cross country. That has always stuck with me. So I was like, “How do Tom Cruise and all these incredible athletes take that flag from Paris to L.A.?” It’s a weird inspiration. 

No, I remember that. I can see the through-line.

Yeah. Then, I pitched it to Tom. He was the first pitch I had. If he hadn’t gone with it, I can’t really think who else would work. Who else is synonymous with action and an American hero? When we got Tom, I felt like the whole thing would work — so we went from there. But it’s been over a year and a half to achieve that. 

How’d you pitch it to Tom? This is the third time you’ve put him in a plane after the Late Late Show segments with Corden.

We developed a relationship these last few years. I think he always trusted us and James to do high-quality stuff. I just pitched to him from start to finish. That first pitch included every element that you saw last night. Only, when I told him, it was a man in a balaclava who jumped from the roof of the stadium. Tom’s feedback was, “I love the idea, only we’re not doing a stuntman in a balaclava. I’m going to be the one who jumps off the roof, and I’m going to be the one who drives through Paris.” Obviously, that’s better for me. The only reason I pitched the balaclava is because it was the difference between a one-day shoot and a four-day shoot plus rehearsals. 

Some things leaked, but you filmed the skydive and the Hollywood sign back in March. How’d you keep it secret for as long as you did? 

When we were filming with Tom, he was never actually holding the Olympic flag. He always was holding a white flag. So, whenever we were photographed with him, the press always said we were filming Mission Impossible. Everyone wonders what was faked and what wasn’t. Interestingly, one of the only things that was faked was the flag. I was disappointed that little things leaked over the last couple of weeks. Suddenly, more and more people need to know what you’re doing when you’re rehearsing in the Stade de France and booking venues.

Such a big deal is made about Tom and the lengths he goes to execute a stunt on his own. I understand who insures him in a movie like Mission Impossible, but what about here, is that your purview? You are putting a very famous man in a risky situation. 

I’m not qualified to answer that. (Laughs.) There will be a team of lawyers on my production team and his team that would know about that. But you’re right. It was definitely a consideration when we were doing the Top Gun stuff for The Late Late Show. It was like, “Well, who does the liability lie with — the show or Tom?” I still don’t know the answer on this one.

Tell me about how the plan changed over the year and a half. There were reports about a few things, including the concert venue changing to Long Beach. 

It’s funny because I’ve seen reports about what was live and what wasn’t live. Not everybody’s a 100 percent right on everything, and I don’t want to comment either way. It’s not fair on some artists to say some were live and some weren’t or whatever. But I think there was a lot more live-in there than people think. Will Rogers Beach was the plan a year ago — and, due to something out of my control, that had to change. With four weeks to go, we didn’t have a venue. That was a stressful moment. Ultimately we got there and I was so pleased with the concert element of it.

Did you ever attempt to actually redecorate the Hollywood sign? 

I did look at doing the Hollywood sign for real. We had engineers up there quite a long time, working out how we could do it. I decided against it because I wanted it to be a surprise. In the end, I think we could have done it, but then in March, the whole world would have seen pictures of the Hollywood sign covered in the Olympic rings. So we did it with CGI. The Tom bit is real. He was up there. He climbed up the sign.

You booked Snoop Dogg, a national treasure and someone so synonymous with Los Angeles, a long time ago — yet his stock has risen even more in the last two weeks. Were you psyched watching him become one of the stars of the Olympics? 

Truthfully, I’ve been in Paris doing rehearsals with Tom and then in London. I only got back to L.A. on Wednesday to start the rehearsals for the concert. Obviously, you don’t get the NBC coverage in Paris or London. But I was seeing online what an amazing Olympics he was having and how everyone was falling in love with him. It was incredible. He was the star of the show. And I knew he was the one who’d bring that flag to the stage. It started with Tom and ended with Snoop. 

Well, I hope you get a bit of a break.

No. (Laughs.) This week we’re filming Ellen DeGeneres’ stand-up show. Really excited about that. And then it’s on to the Paralympics closing. But I did have like 13 hours of sleep last night. I went to bed at 9 o’clock.