Influenced by the reigning icons of the day, Elvis Presley and Buddy Holly, the Furies toured southern California colleges and coffee houses, releasing one single in 1957, "Rockin' Anna," which was a minor, regional hit.

Stewart was selected by the remaining members Nick Reynolds and Bob Shane as Guard's successor, bringing with him his respected skills as a musician, composer, and performer.

Reynolds, Shane, and Stewart recorded a dozen albums together, taking the music of the Trio into new directions, including more original material, and performing songs by relative newcomers Tom Paxton, Mason Williams and Gordon Lightfoot.

The pop-folk era began to wane as the music of groups such as the Beatles, the Rolling Stones, and fellow Californians the Beach Boys increasingly dominated the charts, and in 1967 the members of the Kingston Trio decided to disband.

[6] He later toured with Robert F. Kennedy's ill-fated 1968 presidential campaign and met and married in 1975 fellow folk singer Buffy Ford[5] (with whom he remained until his death).

Teaming up with Stevie Nicks and Lindsey Buckingham (then in Fleetwood Mac), Stewart recorded and released Bombs Away Dream Babies, which made it to #10 on Billboard's album chart and included the #5 hit, "Gold," in 1979.

[5] (Perhaps fittingly, considering the song's cynical attitude, Stewart later stopped performing "Gold" in concert, calling it "vapid" and "empty".

)[8] Two other tracks from Bombs Away, "Midnight Wind" and "Lost Her in the Sun", also hit the Top 40, making Stewart a sudden pop star at the age of 40.

Several of his songs were recorded by a number of popular acts, including Nanci Griffith ("Sweet Dreams Will Come"), Rosanne Cash ("Runaway Train", "Dance with the Tiger"), and Joan Baez ("Strange Rivers").

In 2005 and 2006 Bob Shane attended and performed a few songs with Stewart and Reynolds at the Trio Fantasy Camp, which is held annually in Scottsdale, Arizona.

The production team of CNN's 2019 film Apollo 11 heard the song while listening to archival footage of the flight and included a blend of the astronaut's tape with the original studio recording of the tune in the soundtrack as the craft approached the Earth's atmosphere.

[13][14] In addition to his wife, Buffy, he was survived by their son Luke, along with three children from his first marriage: Amy, Jeremy, and Mikael (a sound technician).