Combining psychedelic and garage rock components, their sound was marked by David Aguilar's lead vocals, songwriting, as well as proto-punk musical arrangements.

By 1969, with Mark Loomis dropping out in the middle of the recording sessions, the band released a final album, One Step Beyond, however it did not include David Aguilar on vocals and was not as highly regarded or indicative of their past work.

The two were joined by Rick Young (bass guitar), Pete Curry (drums), Jo Kemling (organ), and Danny Phay (lead vocals) to form the first version of the Chocolate Watchband, a name that was originally meant to be taken as a joke.

Within a week, the band began performing at local clubs in San Francisco's South Bay, playing a range of songs that included obscure British import tunes that hadn't been released in the USA,[5] so that unlike other local bands who were covering the latest hits from the Top 10, the Chocolate Watchband played songs few people had heard before.

Six months later, after opening for the Mothers of Invention at the Fillmore Auditorium, San Francisco music producer Bill Graham urged the Chocolate Watchband to sign a management contract with him.

Roupe, having secured a recording deal with Green Grass Productions in Los Angeles, introduced the band to producers Ed Cobb and Ray Harris.

Released in December 1966 by Tower Records, the B-side featured the group's cover of Bob Dylan's "It's All Over Now, Baby Blue", another song the band regularly played live.

[5] Frontman Aguilar began writing material for the band, including originals like "Right By My Side", "Gone & Passes By", "Don't Need Your Lovin' Anymore", "No Way Out" and "Sitting There Standing.

They decided to enlist the services of Tim Abbott, Mark Whittaker and Chris Flinders, members of the San Francisco Bay Blues Band.

They managed to secure a place as the opening act for The Doors, and also performed at the KFRC Magic Mountain Festival—the first rock music festival in the United States—among thirty other bands in June 1967.

[11] The group played several dates, including the Oakland Coliseum until late 1967, when Abbott and Flinders had a disagreement with Tolby and manager Ron Roupe over financial matters, which ensured the indefinite break-up of the Watchband in December 1967.

After their dissolution in 1970, a revival of interest in psychedelic and garage rock in the late 1980s and 1990s brought the group to public attention, and their original vinyl releases became collectors' items, selling among private sellers for over USD$100.

[5] Rhino Records issued a best-of release of the band in 1983,[7] while Sundazed and other labels re-issued the original albums on compact discs, including bonus tracks.

[15] Continued interest prompted the band to reunite in 1999, with Dave Aguilar, Tim Abbott (replacing Mark Loomis, who backed out of the reunion), Bill Flores, and Gary Andrijasevich; Michael Reese was added as guitarist in place of Sean Tolby.

The resulting album (This Is My Voice) was released in 2019 to critical acclaim; the lead off single 'Secret Rendezvous' was featured as 'Coolest Song In The World' on Little Steven's Underground Garage program in February 2019.