If there is one overriding takeaway from Kliph Nesteroff’s sweeping The Comedians: Drunks, Thieves, Scoundrels, and the History of American Comedy, it’s that it confirms Shakespearean actor Edmond Kean’s immortal deathbed observation that “dying is easy, comedy is hard.” 

It is hard in so many ways, Nesteroff’s meticulously and painstakingly researched first book relates: vaudevillians had to work under miserable conditions; television killed many the radio star; nightclub entertainers were in thrall to the mob; old school stand-ups found themselves out of date aside the so-called “sick” comics of the 1950s and ‘60s who created material culled from their own lives and neuroses rather than from joke books. And then there’s the primal ineffable hardness of making a career out of making strangers laugh.

The Comedians is an outgrowth of essays Nesteroff, 35, contributed to the website of New Jersey independent radio station WFMU as well as talent interviews. “I wrote, say, about (comedian) Joe E. Ross,” Nesteroff says. “I interviewed Sherwood Schwartz (about Ross), but we would end up veering off-topic to talk about writing for Bob Hope, getting fired by Red Skelton or creating Gilligan’s Island, things not relevant to the article at hand but to me at least were quite fascinating, and as it turns out, to a lot of other nerds as well.” 

He posted the interview transcripts on his own website, Classic Television Showbiz, and between these and the WFMU material, a fledgling following was born. 

Nesteroff was not compensated financially for his essays, but WFMU’s hip cachet (the name is “like a secret handshake among a certain tastemaking cognoscenti,” the New York Times once observed) proved to be invaluable. “WFMU paid by reputation and exposure, because everything good that followed is because of what I wrote for them for free,” he says. “People I have admired my whole life [contacted me to tell me they] are fans of mine. In the past year alone I’ve done shows with Mel Brooks, had dinner with Albert Brooks and received a nice letter from Steve Martin.”

Not bad for someone who grew up in remote Canada in a comedy-deprived household. His mother, Nesteroff says, liked Hee Haw and nothing else. When I did the show with Mel Brooks, I thought I finally would impress her. I said, ‘I’m doing a show with Mel Brooks’ and she said, ‘A friend of yours?’ ” 

Spoken like a stand-up comedian, which Nesteroff was for eight years before moving to the United States. His interest in comedy and its more obscure practitioners was piqued during his years as a teenage record collector and constantly coming across albums by the likes of Woody Woodbury, Vaughn “First Family” Meader, and Rusty “Knockers Up” Warren. “I had no context,” he recalls. “I was curious as to who they were and why they were so popular at some point.”

The reception to Nesteroff’s lengthy, incisive, and informative essays that plumb the arcana of classic show business and pop culture affirmed Nesteroff’s tireless work ethic. “You should treat whatever you’re writing for the Internet as if you were publishing it in a book,” he says. “Fact check, spell check, rewrite. You never know who’s looking at your stuff.”

One person who was looking at his stuff was Marc Maron, host of “WTF,” the essential podcast primarily about comedians and comedy. Nesteroff’s appearance on the podcast three years ago brought calls from a slew of agents and the eventual offer to write “The Comedians.” Nesteroff initially envisioned it as a book about nightclub comedians and the mob. The publisher, Grove Press, wanted a more comprehensive history.

The Comedians spans vaudeville to podcasts, seminal vaudeville monologist Frank Fay to Maron. But for Nesteroff, “comprehensive” was not as important as context in engaging young readers who avoid black-and-white movies, let alone know of Jack Benny, Shecky Greene, or even Lenny Bruce.

“Dual themes of my book are struggle and influence,” Nesteroff says. “Everybody struggles and one generation influences another. Even if they are near and dear to your heart, it’s almost impossible to tell somebody of my generation or younger that a Lenny Bruce, Mort Sahl, or Jack Benny were funny. That’s because generations change and (generally; there are exceptions), a comedian speaks to their generation specifically. If you play a Lenny Bruce record for the same people who like Louis C.K., they may not get the big deal, but if you explain that Louis C.K.’s biggest influence was George Carlin and that George Carlin’s biggest influence was Lenny Bruce, then there’s a greater context for all of this.” 

The Comedians is a summation of Nesteroff’s work to date. And now the punchline: among other projects he’s got lined up (including being hired by Fox to do research for a Bob Hope bio-pic in early stages of development), he’s working on a novel, which, he wonders aloud, is “a terrible career move to change tracks just as you’re becoming known as the guy who does a thing.” 

The novel is based on his “very bizarre summer” running a Death Valley roadside motel. There was a serial killer on the loose at the time. “Across the street there was an abandoned café that was featured in a 1961 episode of The Twilight Zone and that a hillbilly guarded at all times with a shotgun. It ended up destroying my relationship with my girlfriend. I have to go back there and interview people for a piece I’m doing for This American Life. I also have some stuff still sitting there in the middle of Death Valley.” 

Such as?

“A bicycle with a flat tire that I wasn’t able to bring back,” he says. “It’s a bicycle Albert Brooks lent me.” He makes a perfectly-timed pause. “I’ve got a weird life.”

Donald Liebenson is a Chicago-based writer who has been published in the Chicago Tribune, The Los Angeles Times, Roger Ebert.com and the Chicago Sun-Times.