The kind of political comedy I do is not exactly rare. In fact, it is everywhere. From Jay Leno to Dennis Miller, Al Franken to Bill Maher to Don Imus, our culture is awash in political comedy. Many Americans, it’s often remarked, who don’t read the papers get their news from the likes of Jon Stewart and David Letterman. Comedy needn’t have a political purpose. It can just be funny. But at its best, political humor can be subversive, pushing the world in at least a different direction. Rush Limbaugh, a former deejay, who is as much a humorist as polemicist, had this effect 10 years ago, though probably not any more. But, in general, because political comedy is so pervasive, it may have lost much of its ability to be persuasive.

With political comedy now 24/7, it’s startling to be reminded that the art form, as we know it, didn’t exist until about 40 years ago. The early days of stand-up political comedy is the subject of Gerald Nachman’s book, Seriously Funny: The Rebel Comedians of the 1950s and 1960s.

A longtime newspaper critic, Nachman has put together a couple of dozen mini-biographies of what he calls the “rebel comedians” of the 1950s and 1960s, famous angry men like Lenny Bruce, Mort Sahl, and Dick Gregory; intellectual wits with New Yorker sensibilities like Tom Lehrer and Nichols and May; and a slew of TV favorites like Bob Newhart, Bill Cosby, and Steve Allen who it’s hard to think of as rebels at first glance.

For Nachman, as for many historians, the ’50s weren’t an era of Eisenhoweresque consensus. He focuses on the roiling waters beneath the surface of American life–more Rebel Without a Cause than “Ozzie and Harriet.” “Nearly every major comedian who broke through in the 1950s and 1960s was a cultural harbinger: Sahl, of a new political cynicism; Lenny Bruce, of the sexual, pharmaceutical, and linguistic revolution (and the anything-goes nature of comedy itself); Dick Gregory, of racial unrest; Bill Cosby and Godfrey Cambridge, of racial harmony; Phyllis Diller, of housewifely complaint; Mike Nichols, Elaine May, and Woody Allen, of self-analytical angst and a rearrangement of male-female relations; Stan Freeberg and Bob Newhart, of the encroaching, pervasive manipulation by the advertising and public relations culture; Mel Brooks, of the Yiddish-ization of American comedy “

Before the ’50s rebels, Catskills culture dominated American comedy. It was a time, Nachman writes, “in which comedians, clad like bandleaders in spats and tuxes, sporting cap-and-bells names like Joey, Jackie, or Jerry, announced themselves by their brash, anything-for-a-laugh, charred-earth policy and by-the-jokebook gags. Catskill refugees, they were tummlers and shpritzers incubated in resorts, supper clubs, casinos.” The old comedians did mother-in-law jokes; the new ones did JFK. The Catskillians wore suits; the new guys dressed casual. And the new ones often worked “blue,” cursing. It’s hard to imagine how staid sensibilities were at the time. Allan Sherman, who recorded G-rated comedy albums and song parodies–he’s probably best known for “Hello Mudder, Hello Fadder”–was denounced by composer Richard Rodgers as “a destroyer.” The Smothers Brothers’ famed ’60s TV show got canceled because of its long string of anti-war jokes but the proximate cause of their dismissal came when network censors freaked out over David Steinberg’s bit about WASPs tossing Jonah to the whale.

What’s interesting, after reading Nachman’s book, is reflecting on how much political comedy today is essentially content-free. Leno or Jon Stewart may devote 15 minutes a night to a stand-up that’s almost all politics and it’s very funny, but it’s essentially nihilist: “Those guys, what a bunch of idiots,” is the subtext. There’s nothing wrong with that, of course. Comedy shouldn’t have to have a message. Art isn’t propaganda, and most of the political humorists whom we admire from the past, Mark Twain or Will Rogers, for example, were in a similar vein–essentially mocking everything, albeit with a gentler mien. Still, what’s notable is that we have more political humor and less rebellion. Dennis Miller’s “rants” are curse-laden and hysterical, but there’s nothing essentially dangerous or subversive about them.

The same can’t be said for Mort Sahl or Lenny Bruce, who were considered outsized rebels at the time. Sahl faded into obscurity; he started, weirdly, to devote huge portions of his act to debunking the Warren Commission and came to be seen as a kind of conspiracy nut. Bruce, as anyone who’s seen the Dustin Hoffman film Lenny knows, descended into an abyss of drugs, alcohol, and self-indulgence. His comic act became boring recitations of his troubles with police who would bust up his act as “obscene.”

Still, in their day, they were rebels. Sahl took on political topics. Of Bobby Kennedy’s wiretaps, he said: “Little brother is watching.” He had the Borscht belt sexism and made it modern-day: “There are no women in the beat generation,” he said, “just girls who have broken with their parents for the evening.” Asked by Eddie Fisher on TV to say something funny, Sahl replied: “John Foster Dulles.” His trademark sweater and loafers were considered shocking, and NBC forced him to wear a suit and tie on the “Colgate Comedy Hour” before later relenting. And there was an elitism about his act: Peppering his shtick with pop culture from Motor Trend to Time, he’d get laughs by uttering a trendy phrase–communal guilt, group needs, or standard deviation–even if the audience wasn’t quite sure what it meant.

Bruce was edgier. The police would bust up shows for phrases like “cocksucker.” His 1964 New York trial became a cause clebre, with the likes of Irving Howe, Lionel Trilling, and Reinhold Niebuhr signing petitions for him. Still, he was about more than shock. He helped make Jews seem cool and hip before Woody Allen. One of his signature shticks was “Jewish and Goyish”: “Dig: I’m Jewish. Count Basie’s Jewish. Ray Charles is Jewish. Eddie Cantor’s Goyish. B’nai B’rith is Goyish; Hadassah, Jewish. If you live in New York or any other big city, you are Jewish. It doesn’t matter even if you’re Catholic. If you live in Butte, Montana, you’re Goyish even if you’re Jewish. Kool-Aid is Goyish. Chocolate is Jewish, and fudge is Goyish. Fruit salad is Jewish. Lime Jell-O is Goyish. Drake’s Cakes are Goyish. Pumpernickel is Jewish. Balls are Goyish, titties are Jewish. Baton-twirling is very Goyish. All Negroes are Jewish.” As Nachman notes: “He saw humor in everything–in racism; in asking men in the audience if they’d rather sleep with Lena Horne or Kate Smith; in the Holocaust (holding up a fake newspaper with the headline “Six Million Jews Found in Argentina”); in marital relations (husband begging his wife to “touch it just once”).

What Nachman gets is that the seemingly safe comedians could be just as dangerous. The idea that Bob Newhart was as much a rebel as Lenny Bruce seems odd at first. But Newhart–the original Dilbert as Nachman puts it–offered a more comprehensive critique of society. Before his 1970s and 1980s TV shows, Newhart’s comedy albums were huge. His “Button-Down Mind of Bob Newhart” hit number one for a time. His shticks like Abe Lincoln’s PR agent trying to get him to change the Gettysburg address are gentle but knife-edged stabs at a PR culture that waters everything down. In one, he captures everyman’s helplessness when he plays Superman calling the dry cleaner trying to get his cape back: “Yes, the leotards are kind of an off blue.” Who’s to say which is edgier, that or Bruce’s self-conscious rebelliousness?

The same was true of black comedians. When Dick Gregory was out doing edgy racial humor–before he became a long-in-the-tooth activist, a mainstay at save-the-Ukrainian-sea-turtle political rallies–he was funny: “In my home town, they make us take a test to vote–nuclear physics in Russian.” But was it really any edgier than Godfrey Cambridge, the safe Negro from TV who did a great act about liking watermelon but being too embarrassed to buy one? “That big squash over there. Wrap it up. And put handles on it.” Bill Cosby was pushed by his agents and handlers to do racial jokes but rarely did. “I’d do guilt material sometimes,” he said years later. He and Cambridge caught hell for not being black enough in their acts. (He’d do the racially neutral Fat Albert riffs about his childhood and timely jokes about the fast-growing sport of karate but not the explicitly racial.) But Cosby’s color-blindness was, arguably, more revolutionary than Gregory’s doting on race–a point made time and again when Cosby, in the 1980s, became NBC’s biggest moneymaker. In time, Cosby came to be seen as having more racial edge. He gave money to black colleges and seemed less “I Spy.” He worked a little more blue. But he was still essentially the black man all of America loved.

Nachman could have done more to weave the stories together, to offer more analysis and less biography. But this is a smart book and well-timed. Comedy’s become an industry in American life, another corporate product. Nachman reminds us that comedy at its core is rebellious and mischievous, but that the most subversive comics aren’t always the loudest.

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Follow Matthew on Twitter @mattizcoop. Matthew Cooper is Executive Editor Digital at the Washington Monthly. He is also a contributing editor of the magazine and a veteran reporter who has covered politics and the White House for Time, The New Republic, Washingtonian, National Journal and many other publications.