Paul Reubens is doing one of the things he does best: obsessing. "I am constantly hoping that, like, I'm still relevant at all," he says in a voice—higher than most men's, slightly nasal—that's still familiar, even after all these years.

Wandering around the Hollywood Museum, just a few blocks from his star on the Hollywood Walk of Fame, he has lingered over the red-and-white vintage bicycle that he rode in his 1985 movie Pee-wee's Big Adventure. He has appraised the display containing the skinny gray suit (with red bow tie) that was his uniform on his Saturday-morning TV show, Pee-wee's Playhouse, which aired on CBS from 1986 to 1991. But it's not the Pee-wee Herman memorabilia, which sits near W.C. Fields' top hat and Brendan Fraser's George of the Jungle loincloth, that sets off Reubens OCD. Instead, the trigger is Bob Hope's honorary Oscar. "When I was a kid, I'd always watch Bob Hope and go, like, 'I know he must've been funny, but is he past his prime?'" Reubens says. "What I'm trying to prove now is that I still have it, I'm still around—I still am Pee-wee Herman, and Pee-wee Herman is still funny. So I'm feeling very Bob Hope—hoping I don't see a parallel."

Yes, that's right: The 57-year-old actor, best known for embodying the oddball man-child with the puppet friends (and also for two tawdry scrapes with the law), is about to don the skinny suit again to perform as Pee-wee for the first time in 19 years. Starting in early January in Los Angeles, Reubens will star in an elaborate live show in which Pee-wee yearns to fly, gets his wish, and then gives it away. For anyone who likes allegories, as Reubens does, this one is a doozy.

Consider: Since the age of 5, when he asked his father to build him a stage in their Peekskill, New York, basement, Reubens wanted to entertain. After completing high school in south Florida, he went to art school in Los Angeles, where he joined the improvisational comedy troupe the Groundlings and developed a skit about a man-child who wanted to be a famous comic. He took the first name from Pee-wee-brand harmonicas. In a fit of pique, after he lost out on a role on Saturday Night Live—to Gilbert Gottfried, of all people—Reubens borrowed $5,000 from his parents to turn that skit into a stage show. It spawned an HBO special (The Pee-wee Herman Show), two feature films (Pee-wee's Big Adventure and Big Top Pee-wee), and ultimately the hit TV show. Then, while on a self-imposed hiatus from Pee-wee's Playhouse, the once-high-flying Reubens fell to earth.