Smartcuts: The Breakthrough Power of Lateral Thinking

by Shane Snow

Jimmy’s goal since childhood, he explained to Siegel, had been to join the cast of Saturday Night Live. He was endearing. After a two-hour call, Siegel offered to represent him. She had one question, however. “Why don’t you stay and graduate?” Jimmy was a semester shy of a degree. Siegel suggested that they get started in the summer, so he’d have a bachelor’s degree to fall back on, just in case. “No, no,” Jimmy insisted. “I need to get on Saturday Night Live, and you’re going to make it happen, because you know Adam Sandler! I don’t want to do anything else.” Siegel knew this was a long shot—and a long-term endeavor—especially for an out-of-town kid with zero acting credits. But for some reason, she couldn’t turn him down; she had never met someone as focused and passionate about a single dream as this grinning bumpkin from the tiny town of Saugerties, New York. And though his skills were rough, given some time in the industry, she thought he might just make it. “OK, let’s do this,” she said. So, in January 1996 Jimmy quit college and moved to Los Angeles. For six months, Siegel booked him gigs on small, local stand-up comedy stages. Then, without warning, SNL put a call out for auditions; three cast members would be leaving the show. Having worked with one of the departing actors, David Spade, Siegel pulled a few strings and arranged a Hail Mary for the young Jimmy Fallon: an audition at The Comic Strip. SO HERE HE WAS. Fresh-faced, sweating in his light shirt, holding h...