Tom Ruprecht was a writer for The Late Show with David Letterman for 12 years before he jumped ship to pursue a career in looking for work. Also, he wanted to write some books, which he did! His latest is called “This Would Drive Him Crazy: A Phony Oral History of J.D. Salinger” and it’s exactly what it sounds like. After leaving The Late Show, Tom also wrote an episode of How I Met Your Mother and worked as a writer for The Goodwin Games. In this episode, Tom and I discuss the rigors of writing for a daily comedy show, and the slighty-to-very different rigors of writing a book on your own time. We even discuss writer’s block! As usual, this episode has everything an aspiring comedy writer could ever want… except a job offer. Sorry about that. Listen on iTunes.