Stein's unforgettable cameo as the sleep-inducing teacher in "Ferris Bueller's Day Off" (1986) made his face and voice readily familiar to moviegoers, and his mostly ad libbed scenes (painstakingly taking attendance and giving an amazingly boring economics lecture) would live on among the funniest movie moments of the recent past. This role, Stein's second feature appearance (following 1984's "The Wild Life") helped to jumpstart his acting career and led to dozens of memorable cameo performances in films like "Planes, Trains and Automobiles" (1987), "Soapdish" (1991) and "Honeymoon in Vegas" (1992). He also earned a credit behind the scenes, as writer of "Ludes", the novel that inspired the 1988 drug-themed film "The Boost".
A 1989-91 recurring role on the ABC nostalgia comedy "The Wonder Years" was among Stein's more memorable TV performances, but he stayed active on the small screen with guest roles long after his turn on that series was over. Still, it took "Win Ben Stein's Money", a unique game show that pitted successful contestants against the titular host in the final rounds of play, that truly made him a household name. Slightly brainier than "Jeopardy!" and significantly less stuffy, the irreverent "Win Ben Stein's Money" was a hit for the cable network, and the popular Stein additionally hosted his own talk show "Turn Ben Stein On" (also Comedy Central), which enjoyed a run from 1999.