Born as a coffeehouse in the fifties and boomed with folk music in the early sixties. Through the late sixties and into the seventies, the "Troub" was where everybody who was anybody played.

The Troubadour played an important role in the careers of Neil Diamond and other performers, who played engagements there establishing their fame. On August 25, 1970, Diamond introduced Elton John, who performed his first show in the United States at the Troubadour. In that same year, John Lennon and his friend, Harry Nilsson, were ejected from the club for heckling the Smothers Brothers. Randy Newman started out at the club and comics Cheech & Chong were discovered there. In 1975, Elton John returned to do a series of special anniversary concerts.

Other alumni include Lenny Bruce, James Taylor, Bette Midler, Bruce Springsteen, The Pointer Sisters, Sheryl Crow, George Carlin and Rickie Lee Jones.

The Troubadour would also feature New Wave and punk in the late 1970s and early 1980s, and became virtually synonymous with heavy metal bands like Mötley Crüe, Guns N' Roses and W.A.S.P. in the 1980s and 1990s. There are a variety of styles of music played at the Troubadour to the present day.