Ben Stein Also Sings

He has not ordered his food yet, and Ben Stein is already crying. It is terribly discomforting to hear a voice so famously monotone disintegrate into squeaky phonemes. But as he talks about his father, the noted conservative economist who died two months ago, he loses it. The late Herbert Stein forced the Watergate to install a satellite dish in his apartment so he could watch his son's Comedy Central game show, Win Ben Stein's Money. "After every show, I'd call my father and ask him the questions," Stein says. "He'd always say he didn't know the ones I got wrong, even if he did."

Stein's father understood the depths of his son's neuroticism. Although he wins more than three-fourths of the $5,000 trivia contests on the Emmy Award-winning game show, Stein is tortured by his losses. That mix of shock, disbelief and self-hatred isn't rehearsed; he says he sees a $250-an-hour psychiatrist to deal with his fear of losing. Stein's wallet is stuffed with affirming notes from the psychiatrist that say things like "This game does not measure your real intelligence, which no one would ever question" and "You are a star, and they can't take that away from you."

They can't as long as he keeps working so hard to be one. With his hip-nerd uniform of a dark gray pinstripe suit and skateboarding sneakers, Stein, 55, basks in being recognized and, when that fails, in introducing himself to the wait staff by his full name. This week he hopes to up his recognition factor with Turn Ben Stein On, a talk show that airs on Comedy Central Thursdays at 10:30 p.m. E.T., right after his game show. The new show gathers, with mixed results, a small group of culturemakers to discuss a single topic, like high school or growing up in Hollywood. And Stein is trying to develop a sitcom and launch a trivia website called Ben Stein's University. He also sings the theme song to his talk show. He has a full, bluesy, gravelly baritone.

Stein is not a performer by training. A fallen hippie Yale law graduate (with Hillary Clinton), Stein used his father's connections to get a job as a speechwriter for President Nixon (with Pat Buchanan, David Gergen and John McLaughlin), who was then under siege from, among others, Carl Bernstein, Stein's childhood next-door neighbor and Maryland public high school classmate (with Sylvester Stallone, Goldie Hawn and Connie Chung). Although some have posited him as Deep Throat, Stein has always remained a Nixon loyalist. Tapes of Nixon's resignation show Stein crying, and he insists that he was asked to quit the Ford Administration after a few weeks because his loud weeping was distracting the staff.

So Stein became a columnist for the Wall Street Journal, where a rant about racist writing on The Jeffersons led to a job as a creative consultant for Norman Lear. Stein left D.C. for L.A., where he continued to write columns for publications ranging from Penthouse to Barron's, along with screenplays. John Hughes hired him when he was 40 to play a teacher in Ferris Bueller's Day Off, asking him to speak extemporaneously on economics to a class. When Stein received applause from the crew members, he figured it was for successfully explaining the Hawley-Smoot Tariff Act, but they were just impressed that he could act so boring. Thus a career was made, leading to parts on The Wonder Years, Murphy Brown and Seinfeld.

Though he maintains his role as a Pepperdine law professor, an author of 17 books and a contributor to Slate, The American Spectator and the Washington Post, the smartest man on basic cable is most animated when talking about Hollywood and its beautiful women. Perhaps Stein's oddest avocation is being a financial guru to hookers. "Aside from practicing pimps, nobody knows as many call girls as I do," he says. It began when Stein was a columnist for the Journal, spending his afternoons by the pool in his West Hollywood apartment building, which was populated by call girls. "I think I put a couple of them in Berkshire Hathaway and made them a lot of money," he says. His skills are so well known, he boasts, that pros he's never met spot him at bars and ask about mutual funds.

But Stein is an avowed, if preachy, family man. He cries when talking about his dog, Puppy Wuppy, which has a large role on episodes of the already taped talk show and, having been run over, is being stuffed. Stein, who remarried his entertainment-lawyer wife in 1977, has an adopted son. Of all Stein's desires, perhaps the strangest is his Kennedyesque hope that the 12-year-old will be elected to Congress when he grows up. So Stein continues to sweat over the $5,000 each night, hoping to stockpile enough to make his son independently wealthy and complete the surreal version of the American Dream that has shaped Ben Stein's life.

And, no, we are not related.