Happy Sad

Recorded at Elektra Sound Recorders in Los Angeles and produced by Zal Yanovsky and Jerry Yester, it began Buckley's experimental period by bringing in jazz elements. The songs are far longer than before and several depart from the verse and chorus form. David Friedman's vibraphone gives the record a more relaxed tone, and Buckley stopped working with Beckett and wrote the lyrics himself. Strange Feelin' took its instrumental inspiration from Miles Davis's All Blues. Buzzin' Fly dated from his high-school days. Love from Room 109 at the Islander is built from several movements, written separately as Danang and Ashbury Park, and its ocean sound was overdubbed to muffle an electrical buzz. Gypsy Woman is a twelve-minute showcase for his vocal acrobatics. Dream Letter is an ode and apology to his former wife and their son.

The album debuted on the Billboard Top LP's chart dated 19 April 1969 and peaked at 81 during a twelve-week run, the best placing of his career. Trouser Press called it near-perfect and an album of moods, with the only electric instrument Underwood's quietly intense guitar. Friedman joked that the band was the Modern Jazz Quartet of folk. Pitchfork described it in 2016 as the spellbinding result of his fusion of folk and improvised jazz. His experimentation, though, alienated part of the fanbase he had won with Goodbye and Hello. In 2000 it was voted number 954 in Larkin's All Time Top 1000 Albums.