This chapter explores the beginnings of stand-up comedy and the success of renowned comedians such as Jay Leno, Jerry Seinfeld, Pee Wee Herman, Billy Crystal, Robin Williams, and Sandra Bernhard. It also delves into the impact of David Letterman's show on comedy clubs and shares anecdotes about working with Pee Wee Herman and the creation of Pee Wee's Big Adventure. The chapter concludes with a discussion on the importance of failure in a comedian's career and the progress of women in comedy.