1. While Jon Stewart may be the highest paid entertainer in late night (at about $25-$30 million a year), he has a brother who may be just as wealthy. Larry Leibowitz was the Chief Operating Officer of the New York Stock Exchange, and prior to that, he was the chief operating officer of Americas Equities, at UBS Investment Bank, and the co-head of Schwab Capital Markets.
2. Meanwhile, Stewart — who often mocks the wealthy — actually makes more money per day than Mitt Romney, and by some accounts, is worth $30 million more than Bill O’Reilly. Last year, Stewart also sold his Tribeca combo for $17.5 million (or more than three times what he paid for it). His LLC, by the way, is called the Stanley Monkey Trust, named after his pets (Stanley is his cat, and Monkey is his pitbull terrier).
3. A production assistant on a Jon Stewart and Drew Barrymore film that no one has ever heard of, Wishful Thinking, set Stewart up on a blind date with his future wife, Tracey Lyn McShane, who he proposed to using a custom crossword puzzle designed by Will Shortz, the crosswords editor of the NYTimes. His wife is Catholic, and they have two children.
4. Jon Stewart is estranged from his father, who divorced his mother, remarried, and had two other children (Stewart’s half-brothers) with his second wife.
5. Jon Stewart graduated Lawrence High School third in his class, and was voted “Best Sense of Humor.”
6. Stewart had at one point ambitions on being a professional soccer player. In fact, in college (at William and Mary), Stewart started for the U.S. team in the Pan American Maccabi Games in São Paulo, Brazil, a lead-up to the World Maccabiah Games, otherwise known as the Jewish Olympics (his team finished second, behind Brazil). Stewart’s professional soccer playing aspirations were cut short, however, when he blew out his knee.
7. During college, Stewart pledged in a fraternity but dropped out over objections to the hazing.
8. Jon Stewart, whose real name is Jonathan Stuart Leibowitz, was prompted into changing his name after an emcee mispronounced his name during one of his early stand-up gigs (he also decided to change it, in part, because he resented his father).
9. Jon Stewart once played Andy Dick’s twin brother on Newsradio.
10. An asteroid discovered in 2004 is named after Stewart: 116939 Jonstewart