Meet Jonathan Stuart Leibowitz (aka Jon Stewart)

By high school, Stewart was already conversant in politics. He has recalled that he was “left-leaning” and “very into Eugene Debs,” the perennial Socialist Party candidate for U.S. president in the early 20th century. For a mock debate, Stewart was assigned to play another presidential candidate whose politics were light years away from those of Debs’: Ronald Reagan. “I had to defend increased military spending,” Stewart told George magazine in 2000.

Stewart graduated in 1980, reportedly third in his class, and was voted “best sense of humor.” “He was very funny, not funny in the sense that he would tell funny stories, more quick, witty,” says Larry Nichol, Stewart’s 12th grade English teacher. “He’d always be saying something on the way out the door as the bell was ringing.”

“I came to William and Mary because as a Jewish person, I wanted to explore the rich tapestry of Judaica that is Southern Virginia,” Jon Stewart joked as he accepted an honorary doctorate at the College of William and Mary’s 2003 graduation ceremony, wearing a gray sweatshirt beneath his academic robe. “Imagine my surprise when I realized ‘The Tribe’ was not what I thought it meant.”

“The Tribe” refers to the school’s athletic teams, and that Tribe indeed drew Stewart to this historic southern school, not an altogether obvious choice for a Jewish kid from New Jersey. In the 1980s, North-South tensions could still be felt on this conservative campus, which boasted traditions such as the Yule Log Ceremony, where the president dons a Santa outfit and reads How the Grinch Stole Christmas to the student body.

Stewart hoped to play professional soccer and joined the school team. “Jon was very feisty as a player, very high-energy sort of guy,” says Al Albert, the coach at the time, who is also Jewish. “He played out wide. He worked very hard.” After a stint on junior varsity his freshman year, Stewart moved up to varsity, playing midfield.

As in high school, Stewart was acknowledged as a funny man, although no one imagined that his future held a career in comedy. “He was always the locker room cut-up, but we’ve had other locker room cut-ups who haven’t gone on to be comedians,” Albert says.

Between traveling for matches and a rigorous academic load, there wasn’t much time for soccer players to get into trouble. Beers at local delis, MTV, video games and occasional concerts provided their primary entertainment. “Jon was very popular with girls and dated some very attractive women in college,” recalls John Rasnic, Stewart’s college roommate and soccer teammate.

Rasnic remembers at least one incident in which Stewart bumped up against anti-Semitism. During a game against Randolph-Macon College, a liberal arts school in Virginia, Stewart was called a kike. “Jon was a little upset, I think, perhaps a bit surprised, but he didn’t let it bother him,” Rasnic says.

In 1983, Albert recruited Stewart for the Pan American Maccabi Games in São Paulo, Brazil, a lead-up to the World Maccabiah Games, the Jewish version of the Olympics. Stewart started for the U.S. team and, as usual, established himself as the locker room joker. “He created a little bit of levity,” says David Coonin, one of Stewart’s Maccabi teammates, “but everybody was always a little afraid of messing with Jon because he was so quick-witted.”

The 10-day trip included a Shabbat dinner, parties, Brazilian and Israeli dancing and skeptical Latin American Jews. “When we walked out on the soccer field, they called us ‘gringos,’” says Fred Schoenfeld, co-chair of the Pan American Games that year. “They wanted to know if we knew how to play.” The U.S. team proved itself by winning four games, losing only to Brazil in the finals. “After that, they no longer called us gringos.”

On the surface, Stewart seems to have been well integrated into college life. But, as an adult, he would describe his William and Mary days as “miserable” and himself as “a lost person.” Stewart pledged to a fraternity but dropped out, reportedly over objections to the hazing. Having started as a chemistry major, he switched to psychology after two years. “Apparently there’s a right and wrong answer in chemistry; whereas in psychology, you can say whatever you want as long you write five pages,” Stewart quipped to 60 Minutes in 2001.