After spending more than three decades defining humor on late-night television, David Letterman will retire from the Late Show on May 20th. To say goodbye, Rolling Stone met with the comedic legend several times for the magazine’s intimate and illuminating cover story and found the 68-year-old to be characteristically witty and earnest, as well as ready for what lies ahead. Throughout the story, the Late Show host openly discusses his rationale for walking away from his show, ranging from feeling out of place as his late-night rivals generate YouTube viral hits to personal reasons like wanting to raise his son, Harry, and spend time on his ranch in Montana. He also speaks seriously about the eye-opening turning points that shaped his life in recent years, from coping with the public embarrassment of admitting to affairs with staffers to embracing therapy or what he calls an “emotional tune-up.”
