The Greatest Comedians of All Time

In Medieval times, people would jabber in a flop sweat to prevent being beheaded, and before that during the cave-age, people would whack each other for cheap yucks in the nuts. However, the concept of getting on the podium in front of total strangers and talking until the crowd cracks up is relatively new. At most, comedy is about a hundred years old. Some of the greatest comedians of all time are still alive or have not been in the ground for a long time. In its evolution, the genre has given rise to political satirists, one-liner artists, social-taboo tweakers, did-you-ever-notice observational comedians, and many more. From the comedy bubble of the 80s to the boom of the 90s, comedy usually features a relatively simple setup. A woman or man walks into a theater, arena, club, bank, or bar. As they make their way from the podium they usually leave the coed laughing in their wake.

So you would think that compiling a list of the greatest comedians of all time is an easy task right? Ha! This list is based on an evaluation of artistic merit, quality of written material, technical skills, sense of timing, delivery, and overall influence. This list contains the names that have inspired what is expected of a contemporary humorist: A person who can wake us up to the wonderful and weird possibilities of the world around us, and inspire us to see our lives differently–and most important of all, make us laugh like blithering fools.

Richard Pryor

Just like many of the great comedians on this list, Richard Pryor underwent a series of transformations in his work and life. Pryor’s childhood was disturbing with colorful and scary personalities which influenced his early act. He then made his way through a clean-cut Cosby stage, found cocaine, and later burst out a staid Vegas lounge performer, moving to San Francisco and becoming the unfettered, outspoken spirit that made stand-up comedy so much better. At his Prime, Pryor was “King”–so to speak–of comedy. He had the ability to transition effortlessly between puerileness to provocativeness, the humorist might admit to shooting his car’s tires as an act of revenge on his spouse, broaden his lens and talk about police brutality, then talk about what getting a monkey’s penis in your ear is like. Vulnerable and swaggering, confessional and boastful, all-too-ordinary, and superheroic, Pryor put all aspects of his being on display. Even Pryor’s darkest moments were fodder for the comedian’s high-wire humor. Although his personal life wasn’t perfect, he was hypnotic, versatile, and fluid. If George Carlin is the conscience and brain of comedy, Richard Pryor is its heart and guts, and it is highly unlikely that the person referred to as the “Picasso of comedy” by the likes of Jerry Seinfield will ever be topped. 

George Carlin

The First Amendment Activist, the MIT-level linguist, the hippie sage, and perhaps the undisputed champion of comedy, George Carlin was many things. Just like Richard Pryor, George Carline went through various transitions in his life. He grew a beard and got into drugs before finding his voice and crafting witty polemics that prodded and poked audiences out of their socially complicit comfort zones. Watch Carlin at Carnegie or Jamming in New york–hell, listen or watch any of his specials–and you will witness virtuosic and rapid rants filled with potent hypotheticals and sophisticated wordplay. George Carlin was the ideal thinking man’s humorist, asking his listeners to battle from the heap of bullshit placed on them by advertisers, clergymen, and politicians. Carlin’s contempt for any person who would abuse words and his advocacy for free speech gave rise to legendary bits such as, 7 Words You Can Never Say on Television, which remains relevant today.

Lenny Bruce

Even many years following his death, it is difficult to separate between Leny Bruce the icon, and Lenny Bruce the comedian. During Lenny’s days as a comic act, he broke several obscenity rules, battled the police, and fought for his right to speak freely in the courts. What’s more, Lenny Bruce transformed comedy into an outlaw profession. Matching the vernacular and rhythm of jazz with a filthy imagination and feverish wits, Bruce would improvise based on whatever was going through his mind at the time. This ranged from touring, JFK, Jesus, and when he sought to offend those censoring him, the fantastic tits on Eleanor Roosevelt. Lenny Bruce was courageous and would pursue his moment’s truth. His act was sometimes ungainly, meandering, messy, and lacking the ideal punchline. However, it was unlike anything that had ever been witnessed in the history of comedy. This is where the revolution started. Lenny Bruce was both Jesus Christ and John The Baptist of Modern Comedy.

Louis C.K.

For decades, Louis C. K. worked in comedy clubs across America, creating a name for himself alongside other comedians. But somewhere between the time when he imagined his spouse as giving the saddest handjob in the country and calling his 4-year-old son an asshole, a new comic was born with a vengeance. In Louis C.K.’s 2007 show Shameless, he transformed from a comedian slinging absurd one-liners and dick jokes, into a comedian slinging dick jokes and deeply honest stories of the lives of those around him and his own. It was during this time that C.K. started to deliver on a never-before-seen level: The self-deprecating social critic created several new materials every year, and let it go after recording. In the specials, Louis C.K. not only mapped the mind of a gluttonous, horny, lazy, man who is also a father but a tradition of entitlement where everything is excellent and no one is happy. This is the epitome of comic genius.

Chris Rock

Chris Rock comes across like a poet, a boxer, and a preacher all in one when he is on stage. When he begins to pace the stage grinning like a maniac and whining the mic cable, listeners can anticipate what’s coming next. Chris Rock is a comedian who has perfected the art of punching premises for substance as well as rhythm and crafting punchlines that are contrary to conventional thinking. Chris Rock’s technical prowess in terms of working an idea or a crowd is near perfect. More importantly, his ideas on politics, race, and relationships have challenged his audiences to rethink issues that more often than not take for granted: To platonic women, a man is no more than a “dick in a glass case”; In the presence of “bullet control” there would be no need for gun control; Black men are “born suspects.” Some of Chris Rock’s most daring jokes will forever be controversial but impressively humorous for years, and even decades to come.

Dave Chappelle

One thing is clear after taking a glance at Dave Chappelle’s career before and after the Chappelle’s Show: Comedy is Chappelle’s first love. After some fantastic early specials, a much-ballyhooed trip to Africa, and his popular Comedy Central Show, Dave Chappelle made a name for himself as one of the top names in the game. The comic talks about politics, race, and celebrity in a manner that belies the ferocious and incisive nature of his experiences. He is also known to be precocious and finds a hard time staying away from his signature punchline “pussy juicy”. Dave Chappelle treasures the fuzzy line between fiction and truth and loves keeping his listeners on the hook to a point where they scratch their heads to the idea of how a person could masturbate to their own sex video, and whether a child could sell Cannabis Sativa.

Bill Cosby

While it is impossible to separate the man from the performer, scrubbing Bill Cosby’s name from the history of comedy is nearly impossible. As a storyteller and comic, Bill Cosby took the art of comedy to new heights and inspired so many future acts in his wake. Bill Cosby’s long-winded yarns about his marriage, fatherhood, and childhood created impressive images with perfect punctuation with bits of mimes, silly mouth sounds, emphatic proclamations, idiosyncratic speaking patterns, and mugging. Bill Cosby managed to be funny without being controversial and was the champion of comedy in the 1960s and 1970s. Bill Cosby: Himself and his excellent collections of albums put him at the top of comedy’s hall of fame, making him one of the greatest comedians of all time. Although his legacy has since been tarnished, there would be no Louis C.K., Dave Chappelle, or Richard Pryor without Bill Cosby.

This list of the greatest comedians of all time is not meant to be exhaustive, but rather highlights some of the names that have been written on the books of comedy with indelible ink. Many other acts have made significant contributions to the field of comedy, and it is impossible to name them all in one sitting. However, regardless of your take on what makes good comedy, you will find the acts mentioned on this list irresistibly humorous.