From a Long Island teen interviewing his comedy heroes on a high school radio station to the producer, director, and writer behind The 40-Year-Old Virgin, Anchorman, Trainwreck, and more, Judd Apatow is a modern-day comedy icon. He sits down with Willie Geist at New York’s Gotham Comedy Club to trace his rise to fame, from the tough early years and the mentorship of Garry Shandling to how the cancellation of Freaks and Geeks ultimately helped launch a generation of stars. Apatow also talks about his new scrapbook-style book Comedy Nerd, his love of stand-up, and his deep dive into documentaries, including new films on Mel Brooks and Norm Macdonald. Along the way, he reflects on how setbacks shaped his success, and the persistence that’s kept him creating for more than two decades.