Fridays at Enrico’s

Starting in the late 1960s, a group of ­writers got together every Friday night at Enrico’s, a tiny café in San Francisco’s North Beach neighborhood. Sometimes they talked about writing, but mostly they drank, reminisced, and traded insults—the hallmarks of male bonding. The group’s personnel came and went, depending on who showed up to shoot the breeze and liquor up, but the core remained the same: Curt Gentry, the lesser-known coauthor of Helter Skelter; Evan S. Connell, who had risen to literary acclaim with Mrs. Bridge; Richard Brautigan, author of the cult novel Trout Fishing in America; and Don Carpenter, who would eventually mine a decade’s worth of these get-togethers for his final novel, Fridays at Enrico’s.

Brautigan was the de facto leader of the quartet. With his six-foot-four-inch frame, potent charisma, and celebrity, he attracted legions of hangers-on and beautiful women who might not otherwise darken Enrico’s door. Carpenter, on the other hand, was the wingman, whom Brautigan’s conquests turned to for insights into their lover’s mind. The supporting-player motif extended into Carpenter’s writing career: after initial success with his debut novel, Hard Rain Falling (1966), the seven novels, two short-story collections, and many screenplays that followed met with critical acclaim and commercial indifference, yet aspiring writers were eager to pick his brain on the craft of writing, the vagaries of Hollywood, and how to persist at putting words on the page when recognition continued to wait around the corner.

Born in 1931 in Berkeley, Carpenter spent his teenage years in Portland, Oregon, frequenting its pool halls and racking up, at most, an overnight prison stay on minor charges. A stint in Kyoto during the Korean war working at the Army newspaper Stars and Stripes (alongside a young Shel Silverstein, the paper’s cartoonist and an intermittent friend of Carpenter’s over the next two decades) cemented his desire to write. Several unpublished manuscripts and teaching gigs followed, as did marriage and two children, before Hard Rain Falling’s publication.

A year before Carpenter’s 1995 suicide, Anne Lamott dedicated her writing memoir Bird by Bird to Carpenter, a neighbor of hers in Mill Valley, California. He appears only a handful of times in the book—usually by last name—but Lamott brings him to life with a few sentences that betray a wicked sense of humor. In one anecdote, Lamott describes calling Carpenter up and asking his advice on how to ­handle a writer in the throes of envy. He said, “I just listen. They all tell...