10 Best Political Comedians Of All Time

When the airwaves and home pages are flush with story after story of injustice and social discord — as they have been in the days following the announcement of George Zimmerman's acquittal — Americans often turn, desperately, to humor. Humor can contain rage and it can encompass grief. These days it almost always comes with a degree of cynicism. Good comedians can provide us with an outlet for our strongest emotions and when they are politically engaged, their humor can be part of the broader political discussion — even a vehicle for change.

For the millennial generation, political satire has been a prominent component of pop culture since Jon Stewart started hosting the The Daily Show in 1999. The Daily Show, with 18 Primetime Emmy Awards, and its spin-off The Colbert Report have become news outlets in their own right.

However, politically engaged comedy is not a new phenomenon. From the 1950s onwards comics have been vital in breaking down barriers to free speech, fighting for civil rights, and capturing the absurd in our political process. Here are the 10 best (some of the following clips contain NSFW content):

1. Lenny Bruce

Lenny Bruce died nearly penniless in 1966 of a morphine overdose. At the time of his death, Bruce had been left bankrupt by fighting several obscenity charges. Public apologies for getting caught crossing the line aside, it is hard to imagine many comics worry anymore about what they say on stage at a comedy club. However, before Lenny Bruce, comics could be slapped in handcuffs for uttering obscenities in front of an audience. By the end of his life Bruce found himself blacklisted at almost all of the comedy and night clubs around the country and had been barred entry into Britain and Australia. He was a tireless defender of the First Amendment, an opponent of racial inequality, and a critic of what he deemed the moral hypocrisy of organized religious institutions and law enforcement agencies. Though his material was not usually overtly political, Bruce is number one because he led the way for all of the shock jocks and provocateurs to come after him.

2. Dick Gregory

Beginning his stand-up comedy career while serving in the military in the 1950s, Gregory worked his way through the black nightclub circuit to become the first black comic to headline the Playboy Club in Chicago, when Hugh Hefner heard his set and immediately offered him the job. Gregory broke down barriers and performed in front of diverse audiences all over the country. His comedy drew attention to issues of racism and poverty throughout the United States, the American South in particular. He was a fierce critic of the Vietnam War and a prominent participant in the Civil Rights movement, marching with both Malcolm X and the Rev. Martin Luther King, Jr., and participating in several hunger strikes and protests that led to his arrest. He continues to perform stand-up and to speak and write as an activist. 

3. The Smothers Brothers

In the late 1960s, Tommy and Dick Smothers channeled the political and social consciousness of the counter-culture into their Smothers Brothers Comedy Hour on CBS, much to the irritation of the network's censors. When they began in 1967, the Smothers Brothers came off as affable and gentle satirists, palatable to a national audience. But their material would become more and more critical of the U.S. government, leading to the show's sudden cancellation in 1969. The Smothers were talented musicians who pushed the envelope by satirizing politicians in comic songs and inviting anti-war activists such as Pete Seeger and Joan Baez onto their show. Their comedy hour also featured many of the most famous musicians of the time including the Doors and the Jefferson Airplane. 

4. Bill Maher

The host of HBO's Real Time with Bill Maher has been in the game for a lot longer than both Jon Stewart and Stephen Colbert, attacking both sides of the political spectrum with a combative and sarcastic style of satire. Needless to say, he has made himself some high profile enemies over the years. A 2005 bit on Real Time got Alabama Republican Spencer Bachus so angry that he accused Maher of treason. In addition to hosting two of his own programs, Maher's resume boasts a staggering number of comedy specials and appearances on political talk shows. He is also the author of several books. Often dismissed by his victims as a blowhard, after 20 years in the business, Maher still seems to be pissing off all the right people. 

5. Jon Stewart

Since Jon Stewart took over as the host of The Daily Show in 1999, he has been the face of American political satire. In contrast to Maher, Stewart is often earnest and unabashedly passionate about the issues. Stewart's coverage in the wake of the September 11 attacks was a source of comfort to many Americans and for many liberals, The Daily Show was a much-needed outlet for frustration during the Bush years. However, as Esquire's Tom Junod has pointed out, Stewart has held a place in the political peanut gallery for so long that he has nearly lost the right to call himself an outsider. Because he's been given so much legitimacy as a newsman by his loyal legion of viewers, he can no longer ingenuously retreat to the status of comedian. Still, Stewart remains a force to be reckoned with, and nobody has done more for the blending of comedy and politics than he has.

6. George Carlin

Like Lenny Bruce, George Carlin pushed the envelope whenever he could but was not an explicitly political comedian. He never took the side of a single politician or political party. He fought censorship and was a consistent critic of American society as a whole, especially corporate America. To listen to his more than 20 comedy recordings is to hear a brave and irreverent voice rail against the inequities and absurdities of American life from about 1960 through the early 2000s. Carlin was also a humanist, and his comedy tackled the forces- political, social, and corporate — that he felt were holding back human potential.

7. Stephen Colbert

While Jon Stewart essentially hosts The Daily Show as himself, Stephen Colbert morphs every night into a hilariously unaware caricature of a conservative political pundit. Trained in improve at Second City in Chicago, Colbert wrote for the short-lived Dana Carvey Show and SNL before joining The Daily Show as a correspondent. A democrat in his personal life, Colbert is remarkably adept at staying in character. He almost never breaks from his persona as the arrogant but ignorant host of The Colbert Report. However, his digs at politicians are never subtle enough to escape notice. He caused a major stir with his performance at the 2006 White House Correspondents' Dinner. Because Colbert does not bear the weight of liberal spokesman in the way his colleague Jon Stewart does, he can continue to mercilessly savage right-wing pundits and probe the absurdity of our televised political discourse

8. Dennis Miller

Dennis Miller, the only conservative leaning comedian on the list, began his career satirizing the Bush senior presidency on SNL and then hosted his own show on the HBO network where he often covered political topics. Miller has suggested that the U.S. response to the September 11 attacks changed his political outlook and made him an outspoken conservative. He now has a devoted following as the host of his own radio show, The Dennis Miller Show, and often contributes to The O'Reilly Factor in a segment called "Miller Time." At this point, Miller has pretty much abandoned the offbeat, pop-culture laden performances that made him famous on HBO and has taken to delivering angry, and frankly, unfunny rants on Fox News and on his own radio show. If conservatives want to show that they can produce a counter-weight to the Jon Stewarts of the world, they might want to look beyond the current iteration of Dennis Miller. 

9. Janeane Garofalo

Garofalo began her career as a stand-up comic, gaining a reputation for deadpan and witty observational humor. She became a symbol of Generation X apathy in Ben Stiller’s Reality Bites (1994) but later in the 1990s began to introduce her more progressive, left-leaning politics into her act and her on-screen persona. She was a co-host of the Majority Report on the now defunct Air America Radio Network from 2004-2006 and regularly appears as a commentator on Real Time with Bill Maher. Though she can certainly come off as dour and uncongenial, Garofalo is always unequivocally, herself and she has become a champion for gender equality and other issues often left out of the mainstream comic dialogue. 

10. Lewis Black

If Jon Stewart is the affable, down-to-earth guy in perpetual disbelief and Stephen Colbert is the imperious buffoon, Lewis Black is the guy in the post office who has just completely lost it. A regular contributor to The Daily Show, Black was trained as a playwright and only began performing stand-up in the 1990s. However, nobody can angrily contextualize the current state of things quite like Lewis Black. His signature style of rant, which builds in volume and indignation to a great crescendo of madness, is one of the most incredible and impressive spectacles in comedy today, especially because he is an articulate and very thoughtful observer of the modern condition. Let's just hope he doesn't do what we all fear will happen and have a massive heart attack during a performance.