5 Times Jon Stewart Broke on 'The Daily Show'

Jon Stewart made us chuckle, laugh, and outright guffaw during his 16-year run at the head of The Daily Show. But as befits a respected (fake) anchorman, the host generally tried to avoid cracking up on air. It was a valiantly fought battle that he all too often lost, though, as his ace staff of correspondents and contributors accidentally on purpose found a way to make him break. In this video, we’ve collected five memorable instances where Stewart couldn’t contain his laughter on-air. Good luck watching it without breaking.  

John Hodgman (Nov. 16, 2005)
In his first-ever appearance on The Daily Show, author and future Deranged Millionaire Hodgman came out swinging, attacking a clearly unprepared (but delighted) Stewart with his dry, deadpan wit while describing Depression-era America’s hobo problem. Small wonder that Hodgman became a fixture on the program going forward. And each time he appeared, he rarely failed to crack his host up.

John Oliver (Sept. 4, 2013)
Stewart has never missed an opportunity to praise the talents of his premiere U.K. import, who briefly took over The Daily Show while his boss was off directing his first feature, Rosewater. Oliver’s appearance as veddy British cartographer Sir Archibald Mapsalot III illustrates the natural comic rapport the two shared. Is it too much to hope that we’ll see Stewart become a part-time correspondent on Last Week Tonight?

Related: Denis Leary Chastises Jon Stewart for Leaving ‘The Daily Show’

Kristen Schaal (Oct. 8, 2014)
As The Daily Show’s resident Women’s Issues Correspondent since 2008, Schaal has used her pulpit to cheekily comment on such gender-specific subjects as Dad bods and sexy Halloween costumes. In this appearance from late last year, Schaal spoke about what both parties needed to do to win the so-called “lady vote,” using a big bowl of birth control pills (actually mints… we think) as a prop. Stewart manages to retain his composure when she’s cramming them into her mouth, but loses it after she empties the bowl on his desk. On the other hand, we’re pretty sure the studio janitors weren’t laughing.

Stephen Colbert (Nov. 10, 2003)
In a 2014 Reddit AMA, Stewart described getting the unflappable Colbert to break during this classic “Prince Charles Scandal” bit as one of the “greatest joys” of his time on The Daily Show. (Our great joy is watching the two of them crack up together, united in their inability to keep a straight face.) “You felt as though you had accomplished something somewhat Herculean,” he elaborated. “It’s not easy to tickle those folks, but when it happens, you savor it.” Savor it just as you would a ripe banana. (To watch that part of the report, click here.)

Related: Jon Stewart Slams Fox News One More Time

Wyatt Cenac (Dec. 15, 2010)
Based on recent reports, it sounds like Cenac and Stewart didn’t always get along behind the scenes during the comic’s four-year run as a correspondent. But Stewart at least was all smiles (and laughs) when Cenac assumed the puppet form of former Republican National Committee chairman Michael Steele, a role he’d reprise several times. And let’s face it: Puppets are always funny.  

Jon Stewart’s final episode of The Daily Show airs Aug. 6 at 11 p.m. on Comedy Central.