Show Man

Nine Things You Didn’t Know About Jon Stewart

Lisa Rogak’s upcoming biography of the Daily Show host promises to reveal the catcher behind the wry.

Ethan Miller/Getty Images for Comedy Central

Herein lie the many fun facts within Lisa Rogak’s unfortunately titled The Angry Optimist: The Life and Times of Jon Stewart.

Liked The Babes, Laughed At The Bigots

During his two years playing varsity soccer at William & Mary, Stewart was never at a loss for female companionship or anti-Semitic harassment. “Jon was very popular with girls and dated some very attractive women in college,” said a teammate. He went onto add that a member of an opposing team once called him a “kike,” while another made a comment about the size of his nose. Stewart responded that size had never been an issue for him, which got laughs from the crowd and defused the situation.

Bong Stewart

Stewart described his time at W&M thusly: “My college career was waking up late, memorizing someone else’s notes, doing bong hits, and going to soccer practice. A fine institution of learning, and I spent half of it bent over a little plastic tube going, ‘Turn up the jam!’”

A Toasting Before Hosting

From 1984 to 1987, Stewart bartended at legendary Trenton punk club, City Gardens, where he counted Joey Ramone as a regular and invented a drink called The Whack In The Head, which combined a Long Island Ice Tea and an Alabama Slammer. Young people are stupid.

The Jon Stewart Show Gets Baba Booey’ed

Howard Stern was the first guest on Stewart’s 1993’s MTV talk show. Jon was a big fan and he spent hours planning responses to every possible barb. Sadly for Professor Prepared, the interview began with the following Stern summation: “I don’t know who you are and you’re going to be off the air in six weeks.”

Nobody Really Knew What To Do With Him

Before Stewart began his 15-years-to-date stint on The Daily Show, one magazine writer described him as “the celebrity equivalent of lint: he pops up in interesting and unlikely places.”

Getting Colbert To Compare

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Stephen Colbert “reported” for both the Jon Stewart and Craig Kilborn incarnations of The Daily Show and the book is clear on where his loyalties lie. When pressed on what he thought of Kilborn, Colbert replied: “He was really good at treading the teleprompter.”

Stewart As Svengali

Stewart got Colbert to embrace his inner pundit: “[The show] switched from local news, summer kicker stories, and celebrity jokes, to more of a political point of view,” he said. “I didn’t enjoy political humor until I started working on it with Jon, and then I found that I had a stronger one than I had imagined.”

Tiny Man, Big Temper

Stewart often has anger issues, and the book recalls a major blow up he had with Seth MacFarlane over the Family Guy creator’s jokes about The Daily Show filming during the 2007 writers strike. He also threw a newspaper, in a fit, at staff member during a meeting. Said one anonymous former executive: “There a huge discrepancy between the Jon Stewart who goes on TV every night and the Jon Stewart who runs The Daily Show with joyless rage.” Yikes. But how do you really feel, anonymous former executive!


In hindsight, Stewart regretted inviting Yusaf Islam (i.e. the artist formerly known as Cat Stevens) to appear at The Daily Show/Colbert Report 2010 D.C. rally to “restore sanity and/or fear” after getting an angry call from Salman Rushdie. Stewart subsequently went to Yusaf himself and asked whether the singer still agreed with the fatwa against Rushdie, which he received after writing The Satanic Verses.

After some hemming and hawing, Yusaf finally replied with, “Why do you have to insult the Prophet?” Said Stewart of the exchange: “It broke my heart…I wish I had known that, I wouldn’t have done it, because that to me is a deal breaker. Death for free speech is a deal breaker.”