San Francisco's principal entertainment district for white people had always been the North Beach area, the heart of which was on Broadway and Columbus. The Beat Poets had found a home at City Lights bookstore in the 1950s, and cutting edge jazz was the order of the day. The jazz musicians themselves played (and often lived) in the Fillmore district, but North Beach had the best paying gigs. By the early 1960s, the happening music in North Beach was Latin jazz, where San Francisco was a critical outpost. While a very distant second to New York City, of course, San Francisco had played a surprisingly important role in Latin music, and a very important role in jazz as well. While the jazz scenes in New York, Los Angeles and Chicago (and probably Detroit) had more great players, San Francisco was a great incubator for new jazz talent. Throughout the 1950s, San Francisco had been a source of new entertainment for the country, with comedians, folk musicians, jazz and Latin musicians breaking out of the North Beach clubs.
For reasons that aren't entirely clear to me, the early 1960s North Beach club scene came to be dominated by Topless dancers. The most prominent of these (haha) was Carol Doda, the first and for some time only Topless dancer to use silicon implants, who appeared nightly at The Condor. Soon almost all of North Beach had followed suit with topless revues of different types. By 1965, except for a few jazz clubs, almost all the North Beach establishments featured topless dancers.
Topless clubs were an evolution of the existing circuit of Burlesque clubs, which had existed on the West Coast but in a sort of underground fashion for many years. In the 1960s, they came out into the mainstream as Topless clubs. While the attraction of a Topless club was women dancing with their tops off--just to be clear about it--they generally featured a floor show with some combination of musicians, comedians and costume to go with the dancers. Topless clubs were considerably less raunchy than today's Strip Clubs, although it was a somewhat more innocent time. By the 1960s, going to a Topless club was a racy thing for urban adults to do, like going to an R-Rated movie today (which did not in fact exist at that time), but still respectable.
When the Jefferson Airplane started The Matrix in 1965, some blocks away from North Beach, they were establishing a very different kind of entertainment than what was currently available (as I have discussed previously). By 1967, while Topless clubs still ruled North Beach, there were Topless clubs up and down the El Camino Real and San Pablo Avenue on both sides of the Bay, so suburbanites hardly needed to drive into the City for it. San Francisco is always looking for the next thing, and by 1967 what was happening was psychedelic rock. What had been an underground phenomenon in 1966 was wide out in the open by the next year, and the North Beach clubs immediately picked up on it.
The ad above is for a club at 807 Montgomery Street (one block from Columbus and two from Broadway) called The Roaring 20s. Their calling card was a naked girl on a swing who, indeed, swung over the entire building. The club had briefly gone away from Topless in 1966, but had rapidly returned. From looking at the ad (in the May 6, 1967 San Francisco Chronicle) its clear that they have borrowed the iconography of the Fillmore posters, with the wobbly letters and the promise of a light show. Their house band at the time was a group called The New Salvation Army Banned, a Haight Street group who had been playing there almost every night since at least March.
On Sunday, May 14, The Roaring 20s had a special event, promoted in that day's Chronicle (above), The Artists And Models Bal Masque. The blurb helpfully points out that tickets will be available to the public. Another listing says that the Jerry Hahn Trio (a jazz group) and Notes From The Underground (a Berkeley Folk-Rock group) would also be playing.
The New Salvation Army Banned eventually released two albums on ABC, under the name Salvation. For struggling rock bands, Topless clubs were fairly good gigs, if not exactly something to write home about. A band who wanted to work out on "Smokestack Lightning" with some modal jamming was free to do so as long as the drummer kept the beat going, and no one in North Beach cared if your hair was long or if you smoked pot (well, as long as you shared). In cities like Los Angeles, San Francisco and Vancouver (that I know of) many psychedelic rock acts got their start keeping the beat behind topless dancers, and then cheerfully left that out of their resume when they got better known. I'm fairly certain that a band like NSAB, with a seven-nights-a-week gig, could skip out for a Fillmore gig when it was available, and show up later in the evening to finish out the night, so it didn't impede any progress.
Goman's Gay 60s invokes a whole series of images, all of which are in fact incorrect, since "Gay" as a metonymy for homosexuality was not in common usage (if at all). the club was purposely inverting the previous name, and borrowing the psychedelic motif with the light show. No doubt many light show operators got their starts at Topless joints like these as well, although the half-life of light shows was very brief. Goman's Gay 60s did not advertise bands, so whatever combos played there were probably pretty raw, but with musicians moving to San Francisco every day, it was a paying gig. For the club, it gave visiting tourists a chance to get both of San Francisco's entertainment attractions with no cover charge.
Ironically, however, another effect of the Fillmore and Avalon was to reduce Broadway's role in the San Francisco entertainment spectrum. Up until the mid-1960s, entertainment in The City equaled Broadway, but afterwards it was spread all around downtown and the nearer neighborhoods. Broadway remains an important neighborhood for nightlife in San Francisco, but hardly the only one.
update: it appears that soon after the New Salvation Army Banned moved on from The Roaring 20s to greener pastures, their residency was taken up by a band called West Coast Natural Gas, newly arrived from Seattle. For a description of the experience, see here.
(807 Montgomery became the rock club The Orphanage for awhile in the 1970s. Currently neither 807 Montgomery or 345 Broadway appear to feature entertainment venues)