The Heart of Saturday Night

Sessions took place in April and May 1974 at Wally Heider's Studio 3 on Cahuenga Boulevard in Hollywood. David Geffen wanted a more jazz-oriented producer for the second album and chose Bones Howe, who went on to produce and engineer every Waits record until he left Asylum. Waits conceived the album as a sequence of songs about American nightlife, and wrote the title song as a tribute to Jack Kerouac.

The cover is based on Frank Sinatra's In the Wee Small Hours, with an illustration by Lynn Lascaro and art direction by Cal Schenkel. Janet Maslin of the Village Voice found the lyrics vague and the puns ill-advised, while Buddy Seigal of the Los Angeles Times later called it perhaps his most mature, ingenuous and fully realized album. Rolling Stone ranked it 339th on its list of the 500 greatest albums. Deusner of Pitchfork described a small band of session musicians who had played for Ella Fitzgerald and Count Basie, and called San Diego Serenade his most bittersweet break-up ballad.