Jon Stewart has tangoed with a lot of political guests during his 15-plus year tenure, from sparring with Bill O’Reilly to bonding with Barack Obama. But some of my favorite Jon Stewart interviews are those when he gets to interview someone he genuinely likes — more often than not, a fellow comedian — and shoot the shit on all manner of inane topics (while handily avoiding whatever project said comedian has come on to promote). Here are eight of our favorites.
Paul Rudd
After being Stewart's first test guest on "The Daily Show" back in 1999, Paul Rudd went on to be one of Stewart’s most frequent comedy guests, and they always seemed to be having a blast, whether the segment involved Paul Rudd dancing seductively or the "Anchorman" cast's wild food fight. Their farewell interview this week was the perfect mix of tenderness and shameless teasing, with Stewart dubbing Rudd "terrible in every movie" but adding that he'll miss his "effortless sensuality."
Norm Macdonald
Stewart has called Macdonald one of his favorite comedians, which doesn't mean Macdonald is always such an easy guest to wrangle. One of Macdonald's most memorable visits took place back in 2006, when the relentlessly provocative comedian went on an extended riff about the death of Crocodile Hunter Steve Irwin — who had died less than two weeks before — and Stewart oscillated between laughter and discomfort as he tried to get Macdonald to change the subject.
Bob Odenkirk and David Cross
Jon Stewart is a huge "Mr. Show" fan — as he confessed when the pair appeared on the show together in 2013 — and he also loves any chance to hang with Odenkirk and Cross one-on-one. Indeed, when either of them stops by, it turns into an opportunity to reminisce about old times, like last February, when Odenkirk recalled himself and Stewart strolling Greenwich Village at 3 a.m when they were struggling comics. "We had nothing! They wouldn't sell us food, remember? We had money! American money,” Odenkirk riffed.
Ricky Gervais
Anything is fair game when Jon Stewart and Ricky Gervais get together, with the pair cracking up and bantering on absurd, mundane, often NSFW topics, like in 2012 when the conversation culminated in a bizarre dialogue about raccoon sex and panda Viagra.
Steve Carell
Steve Carell was a “Daily Show” correspondent before he hit the big leagues, and whenever he returns for a visit, there really is genuine bromance in the air — like on Carell’s last visit, when the pair tried to “out-compliment” each other as they fawned over their respective film successes.
Denis Leary
Stewart's old pal Denis Leary is one of the show's most frequent guests, which means their interaction rarely constitutes an interview in any traditional sense. Usually it just involves the pair making fun of each other, like in a recent interview where Stewart mercilessly ribbed him with questions like “Why are you in the Amazing Spider-Man; you were already Green Goblin in the first Spider-Man?” and “You don’t polish your scrotum?”
Richard Lewis
The veteran comic has been coming on "The Daily Show" regularly for 17 years, although it was only on Lewis' final appearance earlier this month that we learned their origin story. As Lewis reminisced about early recollections of their time together, Stewart shared memories of their first interaction. As he explained: "The first thing Richard Lewis said to me in my life, and I was a huge fan and remain a huge fan, was, 'I have terrible diarrhea."
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