Tom Waits began his musical career in 1969, performing every Monday night at The Troubadour in West Hollywood, California. His setlist during these "hootenanny nights" mainly featured Bob Dylan covers, along with songs that would later appear on Closing Time and The Heart of Saturday Night (1974). Notable performances included "Ice Cream Man," "Virginia Avenue," "Ol' '55," "I Hope That I Don't Fall in Love with You," "Shiver Me Timbers," and "Diamonds on my Windshield."

During this period, Waits worked as a doorman at The Heritage, a coffee house in San Diego. In November 1970, he performed his first paid show there, earning $25. In summer 1971, while performing at The Troubadour, he was discovered by Herb Cohen, who became his manager. Through Cohen's contacts, Waits recorded demos in Los Angeles in late summer 1971 with producer Robert Duffey, which were later released as The Early Years in two volumes, despite Waits' objections.

To focus on his career, Waits moved from San Diego to Los Angeles in early 1972 and performed more frequently at The Troubadour, where David Geffen discovered him singing "Grapefruit Moon." Geffen was impressed and negotiated with Waits' manager, Cohen, leading to Waits signing with Asylum Records within a month.