Tosca Cafe
242 Columbus Avenue
San Francisco

The Bay Area is known more for its Haight-Ashbury hangouts than for haughty hard-to-get-into nightclubs. Exclusive doesn't really fly in this town, for the exception of the tiny pool room in the back of this North Beach landmark, on the scene since 1919. The place is so legendary, in fact, that late gonzo journalist Hunter S. Thompson used to drink here regularly. Rumor has it he even ran the bar once when current owner and good friend Jeanette Etheredge was out getting a root canal. But these days you're more likely to see people like Sean Penn, Nic Cage and Bono sipping the bar's signature house capuccinos from the vintage espresso machines. "The pool table in the back room is the hardest table to get on in California," one industry insider says. "It's generally understood that you have to be invited to get back there and...no one gets invited." The main room is a real throwback to a 1920s-style speakeasy with dark red vinyl booths, a long mahogany bar and a jukebox loaded with opera classics. Down the street from Francis Ford Coppola's offices, it's often rife with film industry types and used as a location for shoots.

Behind the velvet rope: There is no velvet rope. But good luck getting on that pool table.

VIP privileges: You'll have no problem getting into the main bar, but again, that damn pool table....

Photography by Jason Bennett