Throughout the course of history, standing in front of a hundred strangers and trying to make them laugh for 30 minutes has never been easy. Brain surgery is harder, yes, but you wouldn’t click on the 25 Best Brain Surgeons of All Time. Or would you, you surprisingly well-rounded reader? Doesn’t matter. We’d choose to have brain surgery before we’d write that mess.
So we’re paying homage to the legends of stand-up by naming the best of the best. With two-drinks (minimum) in our bellies we gathered ‘round to discuss the criteria, boiling it down to not only who was the funniest, but also giving ample weight to originality and the size of the footprint they left on America’s comedy scene in the 20th and 21st centuries. In whittling our list down, some greats were left in the green room, but come on; if there’s anything a comedian knows, it’s rejection. And now, for our money, the masters of the tickled rib: the 25 best stand-up comedians of all time, in no particular order (kinda).
George Carlin is the greatest stand-up comedian of all time. Between his brilliant social and political commentary, genius-level observational skills, and legendary command of the English language, Carlin was a true master of the craft. No stranger to obscenity (his “seven dirty words” routine reverberated all the way to the U.S. Supreme Court), Carlin could be crass and juvenile one minute, then deeply philosophical and wise the next. His five decades worth of A-level material will likely never be matched.
No other performer courted controversy with comedy and courage like Richard Pryor did. After having a self-described epiphany in the late-60s about the content of his relatively tame act, Pryor began dropping N-bombs in rapid fire as he simultaneously started speaking bluntly about blacks, whites, and his own personal demons. One of the most influential comics of all time, regardless of race or style, Pryor’s body of work is beyond reproach.
Full of frenetic energy and an almost otherworldly ability to improvise, Robin Williams had more comedic talent than perhaps any other comedian to grab a mic. His stand-up specials in the late-70s and 80s were fast, furious, and full of hysterical impressions, and they paved the way for a hugely successful film career. We’re also gonna call him the funniest talk show guest in the history of the medium.
The definitive groundbreaking counter-culture comedian, Lenny Bruce’s penchant for saying whatever came to his mind on stage earned him genius status and a career-wrecking level of controversy in the 50s and early 60s. While not exactly a laugh-a-minute kind of performer, his fearless choice of material and the language he delivered it with made him one of the most influential performers of any type ever.
Bill Cosby is one of the true legends of stand-up comedy, a pioneer in fact, even if his legacy appears doomed to sink substantially under a startling stack of sexual assault allegations. A master storyteller, Cosby’s humorous recollections of his childhood and his family-friendly musings on life crossed racial and age boundaries at a time when it was extremely difficult to do so, influencing everyone from Richard Pryor to Jerry Seinfeld. Moral lessons were always a huge part of his standout creations, Fat Albert and The Cosby Show, but was he morally bankrupt all along?
Of course most stand-up comedy can be categorized as observational, but Jerry Seinfeld elevated the art form to new heights through his decades of dedication to the craft. Can anyone say “What’s the deal with…” in anything but Seinfeld’s classic nasal tone? Even now in his 60s, with a sitcom-fueled fortune underneath his fanny, Seinfeld is still doing sets, some 40 years after first he grabbed the open mic at New York’s Catch a Rising Star.
The greatest insult comic of all time, Don Rickles made America laugh for roughly 50+ years with his trademark brand of zingers. “Mr. Warmth” spared no one from his jabs, whether it was his buddy Frank Sinatra, women, or minorities, but his lightning quick jokes somehow never rubbed people the wrong way once the chuckle smoke cleared. To Rickles, every performance was a roast.
Bob Newhart has always been one of a kind. With a deadpan delivery, that trademark stammering and stuttering, and those painfully good pregnant pauses, he’s always done more with silence and a stare than most comics can do on full blast—the rare case of a straight being also being the funniest man in the room. His debut album, The Button-Down Mind of Bob Newhart, famously went to #1, knocking Elvis Presley out of the top spot, but that was just the beginning as both of his long-running sitcoms are among the funniest in TV history.
For 30 years, Johnny Carson was America’s warm glass of milk before bed. That may sound tame, but it’s simply a testament to his enduringly irresistible charm and poise in front of The Tonight Show curtain. The Nebraska-born king of late night made millions laugh on a daily basis-—a feat much more difficult than he made it look. He also represented the ultimate goal for any comic: get booked on Johnny, and you’re gold. His kooky characters and celebrity interviews rounded out the package, but it was Carson’s nightly monologue that we’ll always remember and miss.
An Eddie Murphy disciple, Chris Rock’s crackling voice, energetic stage presence, and stinging social commentary helped carve out his own unique path in the 90s. Bring the Pain, his 1996 HBO special, was one of the decade’s finest. Even though his movies have been hit and miss, he still makes you stop what you’re doing and pay attention when he grabs the mic.
Look up “deadpan” in the dictionary and you’ll see a picture of Steven Wright (at least in our dictionary, since we sketched it in). With a tortoise-like delivery, Wright’s brilliant one-liners (“Curiosity killed the cat, but for a while I was a suspect.”) earned him modest fame in the 80s and 90s, and though he’s still tours, we think he’s one of the most underrated comics of all time.
When Steve Martin was on TV in the 70s, people prepared to laugh their asses off. After writing for the Smothers Brothers and other stars he mastered his stand-up game, creating a hysterical persona that was part goofball, part ironic satirist. Whether he was establishing catchphrases (Excuuuse me!), playing some badass banjo, or dancing the King Tut, Martin totally earned his arena-filling rock star status and excellent film career.
Like Kobe Bryant going from high school to the NBA, Eddie Murphy was a teenage phenom. Inspired by both Bill Cosby and Richard Pryor, Murphy was performing in New York City as a teenager, landing a gig on SNL by age 19, and delivering one of the funniest stand-up specials ever (Delirious) at just 22 years old. After years of safe (Shrek) or sucky (Norbit) movie roles, it’s easy to forget how hysterical he was in the 80s, but there was no one hotter in the Reagan era.
Before he became one of the most respected directors in film history, Woody Allen had a stand-up career that was ahead of its time in the 1960s. With a distinct on-stage persona – nervous, neurotic, and whip-smart – Allen’s offbeat, Jewish New Yorker delivery was just as fun as his highly creative material.
A revered comic genius, Jonathan Winters, wove improv, impersonations, and a deep reservoir of oddball homemade characters into his stand-up routines and TV appearances for decades. Much like his protégé and devoted admirer Robin Williams, his creative energy often seemed to be from another galaxy. His career spanned more than 50 years and included many memorable roles, from It’s a Mad, Mad, Mad, Mad World to playing Williams’ dad on Mork & Mindy to handling the voice duties for Grandpa Smurf on TV and Papa Smurf in the movies.
Irreverent, offbeat, and entirely original, David Letterman’s ironic, everything-is-stupid style helped usher in a new approach to comedy that is the norm today. While you might not think of him as a stand up, that is how he first earned the attention of Johnny Carson, his mentor. With the groundbreaking Late Night and the comparatively toothless but still fun Late Show, Letterman was a late night institution, standing up in front of America each night for 33 years, the longest tenure in talk show history
“Can we talk?” In a field dominated by men – remember, stand-up in the 60s and 70s was quite a different beast – Joan Rivers made it in a big way. With her acid-tongued, Borscht Belt style, raspy voice, and self-deprecating jabs (“My best birth control now is just to leave the lights on”), Rivers rose to the elite rank of Johnny Carson’s permanent guest host for The Tonight Show and grew a multimedia empire based on her unique brand.
The two benchmarks any successful comic has to meet are 1) being able to write good material and 2) being able to deliver it well. Louis Szekely (now you know why he goes by C.K.) showed he had a knack for the former, writing for David Letterman, Conan O’Brien, and Chris Rock in the 90s, but in the 00s he also showed his delivery was more than good enough to carry his creative takes on modern human behavior. He was also the first comedian to succeed in bypassing the traditional distribution channels, as his straight-to-the-Web performance, Live at the Beacon Theater, was sold on his site for $5 a pop.
“When I was born I was so ugly the doctor slapped my mother.” Rodney Dangerfield wasn’t the most versatile of comedians, but the one note he consistently played, the self-deprecating loser who gets no respect, was unforgettable. With his bug eyes, head twitches, and a never-ending arsenal of one-liners that skewered his looks, sex life, and wife, Dangerfield was a guaranteed riot every time he took the stage.
You were never gonna finish watching a Bob Hope special with laughter-induced stomach cramps (at least anyone born after 1960 wasn’t), but he was unquestionably one of the elite icons of comedy in the 20th century. Whether he was performing for the troops, in the movies, on TV, or on radio, Leslie Townes Hope entertained America for an astounding eight decades, providing an always reliable source of laughs.
Most people will remember Jay Leno for his two decades behind The Tonight Show desk, with an asterisk that David Letterman and Conan O’Brien deserved it more. And they did. But as a rising star in the 70s and 80s, the Great Chinned One’s observational musings were always funny. Even after becoming a millionaire many times over, Leno’s love for stand-up persisted, as he still occasionally works on new material in clubs across the country.
Dark, jaded, and hyper-critical of popular culture, religion, government, and often his audience, Bill Hicks never had mainstream appeal, and he was fine with that. His shows were spiked by angry rants that, if they didn’t contain so much depth, you’d have sworn they were the work of a madman. His tragic death from cancer at age 32 cut short a career that was 100% unique and unapologetic.
“My friend asked me if I wanted a frozen banana. I said ‘No, but I want a regular banana later, so… yeah.’ Much like Steven Wright, Mitch Hedberg was a master at delivering absurd one-liners, often through closed eyes and shaggy hair. Was he shy? Was he high? It didn’t matter. His gem-to-dud ratio was insanely high, making his death at the age of 37 even more of a painful loss.
A former Pentacostal preacher, Sam Kinison brought fire and brimstone-style fury to each performance. With his trademark scream, Kinison pulled no punches when it came to his punch lines, crafting crass, raw, and X-rated material that was impossible to ignore with his ultra-intense delivery. A fatal car crash at 38 kept us from seeing if old age would’ve mellowed him at all.
A cerebral stoner, Dave Chappelle has always marched to the beat of his own drummer. While his stand-up shows in recent years have been plagued by too many bizarre meltdowns, his excellent earlier work and iconic sketch comedy show locked in his reputation as one of the greats.