In 1960, I read my first issue of Mad Magazine, a bit late in the game actually, as I was 9 and many people discover Mad even younger. I think it had been described to me earlier, specifically the Dave Garraway Today Show parody that featured the famous "Vootie!" That came from 1955, but since Mad readers were avid collectors, that could have been from almost anytime afterwards.
The piece that sticks was "My Fair Ad-Man," a My Fair Lady parody, where a couple of Madison Avenue types make a bet as to whether or not one of them can turn a Beatnik into an advertising man. A couple of recent episodes of Mad Men, a truly fine show on AMC, had encounters between the advertising executive protagonist Don Draper and several bohemians (owing to Draper's affair with a painter) touches on the same dynamic, albeit for dramatic rather than comic purposes. But the contrasts are still there.
The two ad men in the Mad parody find a suitable scruffy beat, and convince him to join in the experiment by promising to get his manuscript published. They then clean him up, to the song parody "With a Little Bit of Soap" (to the tune of "With a Little Bit of Luck), and set him loose on the advertising world. The experiment is highly successful, to such an extent that the beatnik decides he like the ad world ("I've Grown Accustomed to the Pace"). When asked about his manuscript, he tells them "Burn it."
The manuscript was a sequel to On the Road, entitled, Son of On the Road. You also see other beatniks carrying similar manuscripts, On the Road Returns, Daughter of On the Road, Again with the On the Road, etc.
The so-called Beat Generation was a dramatically small group of writers and poets, with only a few of those becoming really famous. The nucleation site was clearly Allen Ginsberg, whose Howl, first performed in 1955 and published by Lawrence Ferlinghetti's City Lights Booksellers and Publishers (it helps to have a publisher who has a bookstore) in 1955. Ginsberg was also instrumental in getting Kerouac's On the Road published, and assisted in the compilation of William Burroughs' Naked Lunch. Ginsberg and Kerouac are sometimes called the Beat Movement's "leaders," a label that neither of them ever accepted. There was also apparently a joke amongst the group about the term "Beat Generation": "Three friends does not make a generation." Among the group that self-identified as Beats, writers like Gregory Corso and Peter Orlovsky are largely unread, outside of college courses.
I'll also interject my own minority opinion that Burroughs is outside of any category except possibly the grand sweep of Surrealism in the 20th Century. It was certainly convenient for him to know Ginsberg, and the Naked Lunch obscenity trial did his reputation as much good as the earlier, similar trial did for Ginsberg's Howl, but if you try to read Naked Lunch back to back with On the Road, you run the risk of explosive decompression.
The other nucleation site for the Beat crew (re-labeled "Beatniks" by San Francisco columnist Herb Caen in the wake of the –nik-ification of all things post-Sputnik), was Neal Cassady. Cassady was a failed writer; his most available work is his posthumously published autobiography, and there are two collections of his letters, also published posthumously.
Cassady has, on the other hand, appeared in at least 12 books, sometimes as a roman a clef character (without Cassady there is some question as to whether or not Kerouac would have had anything to write about), other times as himself. Additionally, there are 4 biographies (one in two parts), plus short stories, articles, and mentions in poetry. And Nick Nolte has played Cassady twice, once in "Who'll Stop the Rain?" based on Robert Stone's Dog Soldiers and "Heartbeat," based on Carolyn Cassady's bio of Neal.
All for a guy who died at 42, from causes that were never fully disclosed. But let's say that it's not a good idea to do massive amounts of amphetamine for years, then take some barbituate, drink a wedding toast, then go for a walk on the railroad tracks and lie down in the cold night when you get tired and sleepy.
Alan Harrington once wrote an article for Playboy, later expanded into a book, Psychopaths, where he used Cassady as an exemplar of the beast, a psychopath, or, as would be said today, a sociopath. My reaction at the time was "Huh? Then what was Charles Manson?"
Cassady was certainly a thrill seeker, a con artist, and a tweaker, more or less addicted to speed, both the drug and bodies-in-motion. Trickster gods are not trustworthy, after all. But I don't see much evidence that he lacked empathy; his behavior was more a matter of always feeling like he was just passing through. There's a reason for traveling salesmen jokes, and there's a reason why kids want to run away to join the circus, whatever the current version of the circus might be.
Cassady certainly joined the circus. He inspired novels, poetry, short stories and movies. He not only hung out with the Beats, he was a major source of inspiration. By all reports, his most significant artistic talent, the speed rap monologue, was lightning that could only be partly bottled. Later, when his attempts at straight life fell apart completely, he joined the next circus to come by, the Ken Kesey's Acid Bus, Further, as driver, mechanic, and whatever else was needed, including, yet again, serving as a character template for others' fictions. Ye gods what a burden to bear.
Cassady appears in the Grateful Dead video that I recently posted, which is obviously why I've been ruminating here. There's a web site from the Cassady family, which claims to be trying to recapture the man from the cage of myth that's been constructed around him.
I wish them all the luck.