When Rob Riggle joined The Daily Show in 2006, he was a Lieutenant Colonel in the Marine Corps Reserve. He was prepared to go back into active duty in order to provide for his family, until Jon Stewart not given him the role that would arguably define his career. Seven years after leaving his post at The Daily Show, Riggle still maintains that Stewart is one of the greatest leaders he’s ever known — and given his military history, that’s saying a lot. EW spoke to Riggle in advance of Stewart’s departure from the Daily Show desk and shared his favorite memories of his former boss.
ENTERTAINMENT WEEKLY: Tell me about the first time you met Jon and what your first impressions were.
ROB RIGGLE: First time I met Jon was at the audition. I did my first audition in Los Angeles with some of the producers and then got the call back to come out to New York, and I went in and he was in the studio, and he was sitting there at the desk. I walked up, we shook hands, he gave me a big smile and made me instantly feel comfortable which I was very grateful for because I was already nervous as all heck, and it was great.
We did a read, and then I went and did the sit-down piece at the desk with him, and then I went and waited in the dressing room while the other guys came in and did their audition, and I thought I had blown it. I really did. I even called my wife and told her, “All right, I don’t think we got this one. My fault.” And I was in the Marines — I was still in the Reserves at the time — and we were hurting for money so I called her and told her, “Hey, I’m sorry, but don’t worry, we’re not going to starve. I’ll go back on active duty. We’ll be fine. Everything is going to be fine, honey.” And then they came in and offered me the job, and I was the happiest man in the whole world.
What’s Jon’s personality like at work? How would you describe him as a coworker?
I’ve been around a lot of great leaders, and he is one of the best. He’s a great manager of people, of his material, of his ship, if you will. He is the captain of that ship.
It’s not in dispute. It’s not in question, you know? It’s Jon. Jon is in charge there and I’m glad he is because nobody knows his show better than he does, nobody knows his style, nobody knows what works best in that environment than he does. As a leader I think he’s one of the best I’ve ever had the opportunity to work for. He’s just good and he’s so not selfish. He just allowed people to flourish. I had just left Saturday Night Live when I came to The Daily Show and it just felt like Jon was on my side. I’ll always be grateful to him for that.
I just got the impression he wanted me to succeed and then I wanted to succeed for him. I think that’s good leadership.
He was everything you’d want in a boss. I was sad when I left. And he was very understanding. When I was on the show just about three years, the whole time I was long-distance from my family.
I was commuting for three years and it takes a toll on a family. And I finally went to him and I just said, “Hey, Jon, you know, I love this show and I love working here and I would stay as long as I could, but it’s been three years and I have to go home. My family needs me, I need to be closer to them,” and he totally understood and he looked and me and he said, “I don’t know how you did it this long.” You know? And there was no friction, no problem.
What’s something about Jon that maybe most people wouldn’t know, or that viewers wouldn’t expect from watching him.
Well, Jon Stewart, for all his success, he has a uniform that he wears. I don’t know if you’ve heard about this. It’s pretty much a grey T-shirt, khaki pants, and work boots. He’s either in his [Daily Show] suit or he’s in that uniform. It’s the most bizarre thing, but that’s what he’s comfortable in so I don’t question it. Every now and then a Mets cap.
Do you have a favorite Jon Stewart memory from over the years? Either a personal memory or something from the show?
When he let me take The Daily Show to Iraq. No show like that has ever done anything like that. It was in 2007, it was at the height of the war. He took a lot of time to sit down and talk with me personally. Because I said, “Look, I’m also going over there to entertain the troops.” W worked on bits and he gave me pointers as a comedian, things to think about that really made a difference over there. My memories of him involve him being patient and gracious with me. My memories are just of fondness and gratitude.
How would you describe his impact on the comedy world?
I think he’s iconic. I think he’s iconic in his own time and I think as time goes on he’s going to get more iconic. He was this wonderful voice that allowed conversation to take place that was sometimes tough to approach. He provided that comedic vehicle to open the door and talk about the war, to talk about whatever issue was out there at the time, talk about politics, religion, war … these things are hard to talk about because people are so entrenched.
But if you approach it with comedy a lot of times you can at least open the door for conversation. For this time in history, I think he was the right man at the right time with the right voice. Whether you agree with him or not, it doesn’t matter. At least he provided a vehicle for conversation, which is what this country needs more of. We need more conversation because right now it feels like everybody is shutting everybody down. If you say one thing you’re labeled. That’s scary because that affects free speech. People are going to stop saying what they mean.
Now that he’s leaving The Daily Show, what would you like to see Jon Stewart do next?
Honestly? Whatever makes him happy. And I mean that sincerely because I know the grind on that show. It is a grind. And no one grinds it harder than Jon. For 16 years and 44 weeks per year, he’s had to bring the funny and he has always delivered. And it’s exhausting. So I hope whatever he does he’s happy and peaceful. I hope he takes a breather and enjoys his family. And then I hope he comes back and kicks ass with some more comedy.
A version of this story appeared in Entertainment Weekly issue #1375, on newsstands now or available for immediate purchase here. For much, much more from Stewart’s former correspondents, EW will be rolling out interviews with Josh Gad, Stephen Colbert, Ed Helms, and many more leading up to Stewart’s final bow.