Talk hippie era San Francisco and the average listener will start thinking of Grateful Deads, Jefferson Airplanes, and, possibly, Quicksilver Messenger Services, but there was an active music scene in San Francisco and Dan Hicks has been part of it since he took up the guitar in 1959. He started off on the folk music coffeehouse circuit before joining seminal SF band The Charlatans in 1965. Hicks took over the drummer's stool after founder member Sam Linde's percussive skills were felt to be substandard.
With a tendency to dress after the fashion of Victorian dandies or Wild West gunslingers the outfit were a significant influence on the emerging counter-culture, with a sound that leaned towards jug band, country and blues influences, though their recorded output was minimal and their self-titled first album didn't appear until 1969, by which time Hicks had flown the coop.
In the meantime Hicks had moved to rhythm guitar, which allowed him to sing his original material as he ended up as a front man for the band but left in 1968 to form Dan Hicks and his Hot Licks with violinist David LaFlamme and two girls allegedly recruited more for their looks than their ability to sing harmonies (though the latter was decidedly helpful).
The Hot Licks were originally the opening act for the Charlatans, but LaFlamme didn't last too long. He ended up going on to minor fame after forming It's A Beautiful Day, and Hicks recruited jazz violinist "Symphony" Sid Page to take his place after sighting him in action when when Hicks took his mother out for lunch on her birthday.
The Hot Licks’ eclectic combination of folk, jazz, country, western swing, bluegrass and gypsy music came heavily laced with a healthy dash of acerbic humour, as evidenced by the title of How Can I Miss You When You Won't Go Away? After 1973's Last Train to Hicksville Hicks chose to disband an outfit that had morphed from hippie jug band into a fairly distinguished bunch of jazzy virtuosos that I’ve seen described as a nimble five-way juggling act (here).
From that point Hicks seems to have been happy to work around the Bay area in a variety of settings, though a glance at the discography will reveal increasing activity as the man hit his sixties and found an anachronistic niche in the twenty-first century. Throughout his decidedly eccentric career, however, the Dan Hicks blend of folk, gypsy jazz and western swing has produced a distinctive body of work that resulted in a devoted cult following.