Plymell got jobs working on post-war "infrastructure" projects across the American West, building roads, pipelines and dams. He also fell into the jazz/R&B club scene in Wichita, a place fueled by Benzedrine, brimming with new fashions and a new sound. A night in jail with artist friend Bob Branaman led Plymell to take classes at Wichita University, which connected him to a new set of cohorts who later became part of the San Francisco art and poetry scene. When he moved to San Francisco in 1962, Plymell took over the lease on a seven-bedroom flat on Gough Street, previously home to a series of Wichita writers and also the place where Allen Ginsberg had written "Howl". A house party, some meth, some LSD, and Plymell soon found himself welcoming Ginsberg and Neal Cassady into his world as his new roommates, as they set about writing out Cassady's memoir "The First Third" under the supervision of Lawrence Ferlinghetti.

Plymell's knowledge of printing led him to create a series of underground magazines while he was in San Francisco, including Zap Comics with R. Crumb and Now with Philip Whalen, and Glenn Todd.

At the same time, Plymell was making himself known as a writer, with David Haselwood's Auerhahn Press publishing his poem "Apocalypse Rose" in 1967. While working on the docks in 1969, Plymell was recruited by two students of Eliott Coleman's to go to Coleman's famed writing seminars at Johns Hopkins University. After arriving in Baltimore, Plymell began work on Last of the Mocassins as his Masters' thesis. His degree led Plymell into a teaching career, where he provided guidance on literature and writing at various East Coast colleges and prisons, while also collaborating with John Giorno to produce The Trashing of America, a now rare and much-sought after poetry collection.

A road trip to Cherry Valley, New York, to the northeast of Cooperstown, led Plymell to buy property there in the early 1970s. After settling into the store buildings where Samuel Morse first created his code, he continued to print and publish underground magazines featuring the work of his friends and visitors, including Roxie Powell, Charles Henri Ford, Joshua Norton, Carl Solomon, William Burroughs, James Grauerholz, Gerard Malanga, and Mary Beach. Today, at 88, Plymell still lives in Cherry Valley with his wife, Pam, and a menagerie of feral cats. He stays in contact with people around the world, and encourages independent thinking, daily, by email.