The Birth of the Cool

San Francisco’s original scenester looks back on a half century of bohemian life with Colleen Hubbard.

“All night parties, free love, I’m up for it.” Diamond Dave Whitaker marvels at the memory of reading a 1957 report in The Nation that convinced him at age 19 to position his Minnesota hometown in a rearview mirror as he set off for the magical west to determine what San Francisco had to offer.

Whitaker has been hip to every scene that breezed through town since the Beats. He met Ferlinghetti, Kerouac, and “Father of the Beats” Kenneth Rexroth back in the late ’50s when Whitaker arrived in the city and picked up work he describes as “bike messenger by day, Beatnik by day and night.” He’s in the background of photos of protests and punk shows from the 1960s through the present day.

Of late, he serves meals with Food Not Bombs, lives in a collective that he describes as a “paradise for cats,” has worked with the Occupy movement, and frequently quotes his own poems in conversation. He has nine children. Now approaching 80, he’s one of the few remaining bohemians from the 1950s who did not move, die, or put on a suit.

Diamond Dave Whitaker. Photo by the author.

Scuffed black paint coats the walls and floors of the pirate radio station where he hosts a weekly variety show; “Happy Chakakhan” declares a holiday poster overlaid with construction paper latkes and dreidels alongside a photo of the funk singer.

Before his show, Whitaker stops at a nearby café; the clerk rings up a $5 tab for a cup of joe, an Arnold Palmer and a canister of coffee to share with guests of the show, a group which includes his musician son Ubi and someone named Rockstar whose birthday is today, an occasion that Whitaker advertises to the café clerk, the pirate radio staff, and acquaintances he passes on the sidewalk.

Of the surprisingly low price, the café clerk shrugs. “There’s some kind of arrangement.”

Whitaker and his son, Ubi. Photo by the author.

Whitaker’s half-century in the city saw the transformation of the New York Giants, the assassination of Harvey Milk, the Summer of Love, and members of Jim Jones’ Peoples Temple abandoning their Geary Street headquarters for an agricultural plot in Guyana. Diamond Dave remembers it all.

He remembers the price of weed in the ’60s ($10 per ounce, Mexican), Richard Brautigan’s Blabbermouth Night reading about pissing into the sink of a dank weekly-rate hotel, Ferlinghetti arranging copies of Howl in the window of City Lights, and the early days of white flight in the Haight when all you had to do to land a prime piece of real estate was jimmy open the window of an abandoned flat and unlock the door to let the party in.

“I have a magnet for folks, a gift for gab, a certain type of…what do you call it? Do I have charisma?” Whitaker wonders aloud.

Among his many claims to fame is introducing fellow Minnesotan Bob Dylan to marijuana and Woody Guthrie, which seem like the unverifiable assertions of someone invested in his own legacy, except that Dylan credited Whitaker in his memoirs.

“Look me up!” Whitaker shouts later across a creaky cell connection punctuated by the pings of a municipal bus that he seems always to ride during phone conversations. “Diamond Dave and Bob Dylan: Google it!”

Read more about the culture of San Francisco in Colleen’s “To Have and Not Hold”: a hippie, an anarchist, and a start-up define freeness and sharing in a time of excess.


Colleen Hubbard is a San Francisco-based writer of fiction and nonfiction. Her work has appeared in Meatpaper, CHOW, The Billfold, and elsewhere.

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