American Comedy Superstars
Comedy occupies a peculiar position in American cultural life-simultaneously frivolous and essential, entertainment and social commentary. The great comedians don’t merely make us laugh; they process our anxieties, challenge our assumptions and force us to examine uncomfortable truths. Since 1960, America has navigated civil rights upheaval, Vietnam, Watergate and political polarisation and comedians have frequently served as truth tellers.
My own education in comedy came through Second City in Chicago, where I started attending revues in my mid 20’s and kept going regularly for 15 years, catching virtually every show. It was a feeder system for Saturday Nite Live. Second City’s improvisational approach taught me to appreciate the comedic arts- the craft behind the laughs, the intelligence required to create humour and the courage to experiment and sometimes fail in front of a live audience. An added bonus is I come from an extended family that competes to amuse; we are sometimes lighthearted, frequently ironic and occasionally biting and sarcastic. In terms of self evaluation, I can self report that am a funny fellow and have keen and sophisticated sense of humour. I know good comedy when I see and hear it so listen up.
This essay examines modern American comedy’s masters, focusing on those who commanded live performance- the most demanding form of the craft. Stand up offers no second takes, no editing, no ensemble to share the burden. Just a comedian, a microphone and an audience. This framework produces a special type of excellence. I have applied no restrictions on the artistic medium- performances in concert, on radio, by tape, on TV or streaming platforms are all “live.” Who are the best- the legends- the Hall of Fame?
1. RICHARD PRYOR: He was a comic revolutionary and any honest assessment must begin with him. I didn’t love him instantly because his raw confessional style initially made me uncomfortable, but I adjusted pretty quickly. Pryor essentially invented modern standup by making the stage his therapy session, processing addiction, racial trauma and personal dysfunction in real time. His concerts were loud, raucous and intimate. His willingness to show weakness and uncertainty set the tone for the generation of angst ridden comedians who followed him. Watch “Live in Concert” or “Here and Now” and you are witnessing someone who refused the safety of setup-punchline comedic formulas. He embodied characters- the wino, his own father with an actor’s commitment and a comic’s timing. His exploration of race was neither didactic or safe. He made white audiences laugh at their own prejudices while making black audiences recognise uncomfortable truths. Pryor proved comedy could be art, autobiography and social commentary simultaneously. Every comedian who treats the stage as an opportunity to explore their personal demons is working in the house Pryor built.
2. GEORGE CARLIN: I first listened to Carlln in my good friend John Iberle’s rather tight basement bedroom. It was the early 70’s. John was cool THEN- ahead of his time and he quickly recognised George Carlin’s talents. I was sold immediately and listened to all his records from that point forward. Carlin was a serious guy- a philosopher really- who happened to be gut busting hilarious. His career tells the story of America’s comedy evolution. He had been as a clean cut observational comedian in the 60’s, then transformed into the counter- culture prophet who gave us “Seven Words You Can Never Say On Television” and then spent his final decades as an angry social critic. Carlin’s late work, including “Jammin in New York” moved beyond joke telling into sustained cultural critique. His routines on politics, religion and American hypocrisy were comedic lectures by a furious humanist. He trusted his audiences, challenged them on tough topics and still made them laugh.
3. BILLY CRYSTAL: He represents something increasingly rare- a complete entertainer who excels across multiple formats. Unlike Pryor and Carlin, he is warm and fuzzy. Crystal’s career demonstrates that mastery of craft and likeability are not mutually exclusive. You can be technically brilliant without becoming cold, distant or cynical. Crystal’s standup work, particularly his HBO specials like “Midnight Train to Moscow” showed someone who could command the stage alone. He combined observational humour with character work and impressions. His Fernando Lamas character on Saturday Night Live (“you look marvellous”) became a cultural catchphrase. His Sammy Davis Jr impression was brilliant. His hosting work at the Oscars showed the entire country how he could improvise, read and hold an audience and make scripted material feel spontaneous. His opening monologues became a highly anticipated event. His film work showed range beyond pure comedy and his one man show”700 Sundays” confirmed that he could still fill Broadway theatres in his 60’s.
4. ROBIN WILLIAMS: A true improvisational genius. He approached comedy like a jazz musician, following inspiration wherever it led, trusting his technique and wits to keep up with him. His stand up specials, “An Evening with Robin Williams” and “Live on Broadway” were basically unguided comedic missile attacks, with Williams riffing on everything from politics to Shakespeare to the voices in his head. His speed was extraordinary- generating amazing material in real time He also had range. He could shift from childlike innocence to dark cynicism, from gentle observation to savage political commentary, from highbrow literary references to lowbrow and slapstick physical comedy within the same routine. Unlike comedians who maintained ironic distance, Williams wanted to connect, His vulnerability was different from Pryor’s, but it was there. His film career was also noteworthy. “Good Morning Vietnam” let him improvise radio sequences that captured his comedic genius. “Moscow on the Hudson” revealed his ability to play a Russian defector with manic energy and general pathos. His suicide shows there is often despair behind the laughter. He was sui generis.
5. EDDIE MURPHY: He arrived on Saturday Night Live in 1980 and essentially saved the show during its most precarious period. His signature characters were Gumby, Buckwheat and Mister Robinson and his routines became water cooler chatter at the office on Monday. His standup specials “Delirious” and “Raw” broke box office records and definitively established that a black comedian could command massive mainstream audiences. Murphy’s comedy worked across racial lines. His impressions of James Brown, Bill Cosby and Stevie Wonder captured the world of black celebrity and his routines about family and relationships had universal appeal. He then maintained his mojo in films that could not have existed without him: “Trading Places”, “Beverly Hills Cop” and “Coming to America.” His ability to create unique characters showed extraordinary range.
6. STEVE MARTIN: His early standup work was radically different and insanely funny. He focused on the absurd and made it work for the masses. His late 1970’s performances and albums like “Let’s Get Small” and the “wild and crazy guy persona” were legendary. The audience frequently wondered whether they were in on the joke or whether the joke was on them. He ignored the traditional comedic structure of setup and punchline and instead did skits using, banjos, physical comedy and arrows through the head- all designed to highlight the world’s fundamental absurdity. He brought avant garde sensibility into mass culture. He advanced from small experimental theatres to large stadiums. He later took risks in films and became a mainstream, if amusing, film star. He evolved and wrote plays, art criticism and novels- showing he viewed comedy as just one form of creative expression. He was an innovator and a winner. I saw him in person multiple times in early career tour appearances in Chicago.
7. JON STEWART: I may get some pushback on this one, but I am a believer. He is a comedian who became America’s most trusteed news source. On “The Daily Show”, Stewart had a fifteen year run and used his comedic talent and timing to cut through partisan spin and corporate news timidity. He proved satire was not just about mocking the powerful but explaining complex issues in ways mainstream media either wouldn’t or couldn’t. The comedians who emerged from his show- Colbert, Oliver, Bee learned that comedy could actually provide public service. He was edgy, tough and funny.
8 JERRY SEINFELD: In an era where comedy increasingly meant revealing your personal demons or engaging in political commentary, Jerry Seinfeld committed himself to pure observation. No politics, no agendas- just a relentless focus on the absurdities of daily life. His stand up work and his sitcom both asked the same question- Isn’t life super strange? His comedy was deceptively simple. He had great timing. He was a craftsman who approached joke construction and delivery with a watchmaker’s precision. His insistence on a relentless focus on the mundane hit a home run with audiences. Remember 90% of life is mundane and the other 10% is ridiculous and absurd. Some think he was lightweight, but I believe he is exactly the opposite- most successful comedian for an entire decade.
9.JIM CARREY: Physicality is important and Jim Carrey was the master of physical transformation. Unlike comedians who rely on language, Carrey’s special gift was his rubber faced ability to contort his body and features in ways that seemed inhuman. His early standup work in the 1980’s revealed his talent, but he exploded in the 90’s. “Ace Ventura:Pet Detective”, “The Mask” and “Dumb and Dumber” established Carrey as a world renowned comedic force. He was versatile in these silly movies- displaying a bizarre physicality, vocal gymnastics, cartoonish faces and an animated elasticity. His willingness to commit to outrageously stupid characters made him a legend. Carrey’s physical comedy was athletic and he seemed to know what every muscle was doing and why. His later career took surprising turns with “The Truman Show” and “Eternal Sunshine of the Spotless Mind.” He then retreated from public appearances and is now seen as rather strange fellow.
10. BILL MURRAY: This is homer pick- Bill Murray is Chicago guy- Loyola Academy - Cubs and Bears fan. He is uber talented and his SNL work and film career show his terrific range and versatility. He specialises in playing characters who are simultaneously ridiculous and real. His best SNL characters were”Nick the Lounge Singer” and the “Shower Mike Guy“ and they worked because he balanced mockery with affection. His Weekend Update segments with Chevy Chase cracked with genuine tension that made the comedy sharper. His film work showed similar instincts. “Stripes”, “Caddyshack”,”Ghostbusters”, and “ Groundhog Day” gave him perfect vehicles to show his stuff. He represents comedy as a coping mechanism and humour as a survival strategy. His later success as a dramatic actor stunned me, but kudos to him.
One of the more remarkable phenomena in modern entertainment is how successfully standup comedians transitioned to film, despite rarely matching Hollywood’s leading man template. Messrs Murphy, Williams, Crystal. Martin, Carrey and Murray did not look or sound like conventional movie stars. If anything, they represent the opposite: regular guys, character faces and an unconventional presence. I can only speculate why. My gut is that comedians learn to read audiences in real time, adjusting delivery based on immediate feedback. They understand timing and have mastered the art of connection. These skills translate powerfully to film. The camera captures authenticity and comedians have the ability to genuinely connect with audiences. Plus, they are everyman- the opposite of elitists. They know how to make people feel something- laughter being just one emotion in their arsenal.
The list above is obviously personal and arbitrary. There are many other talented and influential comedians who deserve a shout out. Chris Rock, David Spade, Phil Hartman, Dan Akyroyd, John Belushi and Will Ferrell are world class. The foundational figures from an earlier generation also merit recognition. I am thinking Lenny Bruce, Jonathan Winters, Rodney Dangerfield and Joan Rivers. Finally, there is a scarcity of women on this list. I apologise, but it reflects the reality that comedy clubs were historically male spaces and women only recently began to appear as headliners. There was a double standard about appropriate subject matter- too sexual and you are vulgar and too feminine you are boring. Besides the pioneering work of Joan Rivers, there are several other women who are uber talented comedians and comedy writers. Gilda Radner, Tina Fey, Kristen Wiig, Amy Poehler, Wanda Sykes and Ali Wong should take a bow. The tide may be turning and the arrow is pointing straight up for female comedians.
I have gone on too long which isn’t funny. Let’s wrap it up. The best comedians diagnose culture while making us laugh. Comedy demands honesty and audiences detect inauthenticity immediately. The bar is high, but this creates curious situation where people dismissed as mere entertainers often tell harder truths than politicians or journalists. The comedians honoured above had vastly different styles. What unites them was a willingness to take risks and trust their audiences. They understood that the best comedy changes us- makes us more aware, more honest and more willing to examine ourselves. Their work endures because they grasped an essential component of the human experience; laughter isn’t frivolous- it is how we survive!
