As longtime viewers know, Stephen Colbert’s time on The Daily Show actually precedes Jon Stewart — he was a correspondent back in the Craig Kilborn days. But after Stewart’s arrival, Colbert became an integral part of the series and helped set the tone for a generation of Daily Show correspondents. He would of course go on to host The Colbert Report, co-host The Rally to Restore Sanity and/or Fear, and take over a little thing called The Late Show on CBS — all while becoming good friends with Stewart. In an interview with EW, Colbert tells us about working with Jon, including the story of how they first met.
ENTERTAINMENT WEEKLY: Tell me about your first encounter with Jon. What were your first impressions?
STEPHEN COLBERT: The first time I met Jon Stewart was at the press conference that Comedy Central held to announce Jon would be the new host of The Daily Show, which back then was not called The Daily Show with Jon Stewart. We all figured out it was going to be called The Daily Show with Jon Stewart because the Christmas cookies the network sent out to us were mistakenly frosted with the new logo that his name on it — so none of us were surprised. Bakers always know what’s going to happen with a TV show first.
So, I heard that there was going to be a press conference that day announcing that Jon was going to be the host, and I said, “Well, wouldn’t The Daily Show cover something like this?” So I left the offices and went over to Comedy Central, and I stood up and said, “Stephen Colbert, The Daily Show. In what way does this announcement affect my chances of becoming host of The Daily Show?” Jon Stewart turned to the president of the network and said, “You told me he wasn’t funny.”
How would you describe Jon’s personality at work? His style as a boss or as a colleague?
Like no one I know in the world, Jon has clarity. He expresses clearly how he sees a story or a comedy bit. That’s a great gift to everyone who works for him, because you know whether or not you’re giving him what he asked for. That said, he’s always open to other people’s ideas. Best idea wins.
Do you have a favorite off-camera memory of Jon?
My favorite off-camera memory of Jon Stewart is watching him jump from the second level of a tuna tower into the waters off Grand Cayman. It’s a long story. And a good one.
And a favorite on-camera one in general? Sort of the archetypal Jon Stewart/Daily Show moment.
My favorite memories of Jon are making him laugh. There is no greater joy in the world than to sit at the desk next to him and though he knew the material already and was part of the team that wrote what you were about to say, you are cracking him up. I’m sure he did funny things too, but all I cared about was being funny for him.
Tell me something funny about Jon that most people wouldn’t know.
No — if Jon wanted you to know, he would tell you. That said, he’s got hair in some odd places!
What would you, personally, want to see Jon do next?
Mostly I want him to say, “I was just kidding. I’m not going anywhere.”
A version of this story appeared in Entertainment Weekly issue #1375, available for immediate purchase here. For much, much more from Stewart’s former correspondents on his legacy, see below.