Conan O'Brien:
TV's quirkiest late-night host says the best humor "creates an uneasiness."

By Jeffrey Zaslow  --  USA Weekend  --  September 13, 1998

 As Aug. 17 approached, Conan O'Brien expected a red-letter day. President Clinton was set to testify in the Monica Lewinsky case, so on his late-night show, O'Brien labeled the day like a movie rating: "NC-17." His audience laughed, some of them nervously, all of them knowingly.

This is the most fertile period ever for the melding of political and blue humor. It's uncharted territory, and O'Brien is a leading practitioner. When he jokes that Lewinsky always makes sure her shoes match the spot on her dress, he sets the tone for jokes that crisscross the country. There's no exact line he won't cross. "Audiences let you know. You quickly find out who they're willing to laugh at and who they're not."

Scorned by critics when he took David Letterman's old job at NBC's Late Night in 1993, the former Simpsons writer has since crafted his show into a quirky hit. This week, his first prime-time special highlights the topical humor that now has critics calling his show the smartest hour in late night.

The best humor, O'Brien says, "creates an uneasiness" -- but it needn't be mean. Is it OK to make fun of Linda Tripp's looks? Jay Leno says yes, because she's "a backstabber." O'Brien holds back; he's killed jokes. He may be sensitive about physical-appearance humor because he's not stereotypically telegenic. As a kid, "I thought Bob Crane from Hogan's Heroes looked the way men were supposed to look: black hair, handsome. My only role models were Howdy Doody and Ralph Malph on Happy Days."

The best jokes aren't about things beyond people's control, like looks, O'Brien says. He targets people who ask for it "through their actions." That makes Clinton fair game. Did he wear Lewinsky's tie as a secret signal the day she testified? Maybe not, says O'Brien, "but he still can't explain why he was also wearing a beret."

Give the positive spin:
O'Brien was almost a footnote in TV history. "I used to tell myself that even if the show was on for just five days, I'd still be in the TV encyclopedia with Johnny Carson and Petticoat Junction."

"If you apply the must-succeed-every-time standard to a creative thing, you ruin it."

Don't be awed by Harvard grads:
"I met brilliant people when I went to Harvard and I met stupid people who couldn't tie their shoes. When they caught the Unabomber, everyone said, 'Oh, my -- and he came from Harvard.' I'm surprised there weren't more Unabombers from Harvard."