Choosing only 10 stand-up comedians as the ‘smartest-of-all-time’ is like asking a parent to choose a favorite child – someone WILL get hurt. There’s obviously some very honorable mentions not here, but including everyone worthy of recognition would make this a top-500 list. Instead, I chose to choose a blend of ten classic & modern comics that drastically changed the medium, not by just making you laugh – but by really making you think.
(NOTE – most videos are NSFW.)
- #10 – Mitch Hedberg
Not since Cheech & Chong has an ambassador of stoner-dom gained such a cult following. However, whereas C&C were heavy on actual drug material, Mitch Hedberg simply seemed lit up. Known for his one or two lined non-sequiters, he was easily dismissed by critics as a “pun-jockey surrealist” – but his massive cult following heard a depth to his jokes.
Hedberg had a way of noticing the little things of life – ironies, word-play, inconveniences – by conveying them in such a likable way you felt like his drinking buddy by the end of the show. Outshining his “duuuude” image, he formulated his stage presence into a remarkably unique delivery, one that almost appears forced when seen for the first time. In reality, he severely struggled with both crippling stage fright (you can regularly see his microphone-hand trembling) & drug addictions, leading to his early death by overdose in 2005 at the age of 37.
THAT’S FACTED UP: Hedberg made an appearance on “That 70′s Show” as Frank, chef of the restaurant the characters frequent.
NOTABLE QUOTABLE: “I’m sick of following my dreams, man. I’m just going to ask where they’re going and hook up with them later.”
- #9 – Steven Wright
Comedian (also actor / writer) Steven Wright made his unique breakout in 1985 - striking extreme contrast half-way through the decade of excess. What defined the 80′s is exactly what his act defied. Almost an existentialist, his thought-provoking material delivers itself SO casually, you’re laughing too hard to realize that what he just said was a complete mindfuck.
Wright is the Mitch Hedberg for connoisseurs. Underneath a thick level of deadpan, Wright’s routine bordered on the philosophical – usually in increments of one-lined jokes. A master of the double-entendre, his routines were so languid HE almost seemed bored – which allows the incredibly insightful statements he peppers throughout the act to absorb slowly. His type of humor wouldn’t work well with an energetic, charismatic-type figure – these are dull, ironic & listless jokes – that are brilliant.
THAT’S FACTED UP: Wright lends his voice to Quentin Tarantino’s 1992 “Reservoir Dogs” as the voice of the DJ on ‘K-Billy Radio’.
NOTABLE QUOTABLE: ”I was born by Cesarean section, but not so you’d notice. It’s just that when I leave a house, I go out through the window.”
- #8 – Sam Kinison
Arguably the loudest & most vitriolic comic on Earth, Kinison made it known he was in the room. As a former Pentecostal Preacher, his transformation into comedy was distinctive – evangelical, literally-screamed punchlines became the cornerstone of his act. He moved to stand-up shortly after his first divorce (and subsequently leaving the Church), using his massive lifestyle change as fuel to the angry fire & brimstone of his set.
Having an open appetite for drugs, sex & alcohol brought an edge to his personality: here was once a man of the cloth, holy in behavior – now pissed off, hedonistic and loudly sacrilegious. This sort of duplicity helped make his image infamous – besides, it’s pretty hard to ignore the guy shouting in your face. Aside from the bad-boy infamy, Kinison brought angered reason to everyday-topics like marriage, life & religion in a way no one previously had. Kinison died due to a drunk driving accident in 1992 at the age of 38.
THAT’S FACTED UP: Kinison played Al Bundy’s guardian angel in an episode of “Married… with Children”. Ironically, Kinison was also the network’s original choice for the role of Al Bundy (which he turned down).
NOTABLE QUOTABLE: “I called a detox center – just to see how much it would cost: $13,000 for 3 weeks! My friends, if you can come up with thirteen grand, you don’t have a problem yet.”
- #7 – David Cross
If you’ve watched television between the mid-nineties and now, you’ve seen David Cross somewhere. Best known for his roles on “Mr. Show” & “Arrested Development”, Cross has transformed character acting into a crossover art – writing, directing, voicing or starring in over 35 shows and 40 movies as of 2012. Aside from Hollywood work, Cross’ biting stand-up routines have been an indie-favorite for almost 30 years.
His scathing reflections on religion, politics, sexuality and culture have solidified him not just as a left-leaning ‘hero’, but as a legitimate advocate of basic human & animal rights. Performing stage comedy since the age of 17, Cross’ notoriety includes a famous public dispute with fellow stand-up Larry the Cable Guy, multiple lawsuits and even a scandal involving him snorting cocaine at a White House Correspondence dinner near President Obama (just to say “he did it”). Despite his apparent political angle, Cross continues to be a cross-party, crowd-pleasing figurehead for an entire nation of American life.
THAT’S FACTED UP: Cross lost the role of Dr. Gregory House on “House M.D.” to Hugh Laurie.
NOTABLE QUOTABLE: “I don’t think Osama bin Laden sent those planes to attack us because he hated our freedom. I think he did it because of our support for Israel, our ties with the Saudi family and our military bases in Saudi Arabia. You know why I think that? Because that’s what he fucking said!”
- #6 – Eddie Izzard
English actor / comedian Izzard has confused almost every critic with his short-listed bio: he’s a sexually-straight (but) cross-dressing, dyslexic, atheistic, trilingual, award-winning, accomplished theater / film / television actor; with one hand in British politics & the other in professional athletics. Boosh.
Best known in America for his roles in “Ocean’s Twelve”, “Ocean’s Thirteen” & ”The Riches”, Izzard has been called “the Lost Python” by John Cleese himself (even appearing on-stage with Monty Python in 1998). His multi-faceted biography mirrors his act - rambling / erratic observations colorfully paint his interesting portrayals of world history, religion and culture in a way that makes even anti-intellectuals listen. If the education system was more like this, graduation rates would skyrocket – his routines are study guides with a sense of savvy sarcasm.
THAT’S FACTED UP: Izzard ran almost 30 miles a day, 6 days a week – for 2 months straight – to help raise money for charity in 2009.
NOTABLE QUOTABLE: “I grew up in Europe, where the history comes from. ”
- #5 - Louis C.K.
Widely heralded as the “comic’s comic” – Louis C.K. brings unashamed, unfiltered honesty to the stage that America hasn’t seen in decades. Taking a no-gimmick approach, C.K. has perfected an “everyman” persona – publicly evaluating his life, love, children, work & society in a way that makes almost every demographic relate. Treating his audience like a personal therapist, his act routinely outs his shame, guilt, struggles & hardships, all without asking for sympathy.
C.K. uses a technique that seems blatantly obvious – truth. The difference between himself & current peers, however, is his quelling of ego. This is a self-realized man in his mid-40′s, dealing with the same problems John Doe down the street has. Despite the centralized personal theme to his material, his reflections of society are fundamentally how it really is. Starting his professional career as a writer for A-listers like Letterman, Conan, Ben Stiller & Chris Rock – he’s successfully transitioned into television & film (screenwriting and directing for others & even independently creating 2 auto-biographical primetime shows). Insightful yet modest – tragic yet empathetic – Louis C.K. is one of our greatest modern voices.
THAT’S FACTED UP: Despite popular belief that he is fully Irish, C.K. has partial Mexican ancestry – even living in Mexico City until he was 7 years old. English is actually his second language.
NOTABLE QUOTABLE: “There’s a reason it’s called Girls Gone Wild and not Women Gone Wild. When girls go wild, they show their tits. When women go wild, they kill men and drown their kids in a tub.”
- #4 - Lenny Bruce
Lenny Bruce (born Leonard Schneider) was the Elvis Presley of comedy. He came at a time, like Presley, when this type of public-spectacle just didn’t happen. These were the 50′s: clean-cut, wholesome, willingly-sterilzed times. Bruce was approximately the exact opposite. Earning himself an infamous obscenity conviction during his trial in 1964 blew the doors open for an entirely new brand of humor: black comedy in a bright, white world.
Bruce’s social satire & unflinching, free-associated honesty portrayed a darker American image than it’s public was used to. His routines were philosophic – light years ahead of their time. Appearing on national television only 6 times, Bruce encountered constant court battles and was blacklisted by almost every American club by the end of his life. Later in his career, drug addiction & close-to-public-breakdowns affected his fame and fortune, leading to a morphine overdose in 1966 at the age of 40. The legacy he left behind has continued to influence the genre, with most comics citing him as the “original visionary”.
THAT’S FACTED UP: Apart from his comedic influence, Bruce’s likeness appears on the cover of “Sgt. Pepper’s Lonely Hearts Club Band”, has been mentioned in-song by R.E.M. and Simon & Garfunkel, and is the first case in New York state history to be granted a posthumous pardon in 2003.
NOTABLE QUOTABLE: “All my humor is based upon destruction and despair. If the whole world were tranquil, without disease and violence, I’d be standing on the breadline right in back of J. Edgar Hoover.”
- #3 – Richard Pryor
Richard Pryor did for African-Americans in comedy what Rosa Parks did for political & civil rights. His racially-driven, controversial material helped usher in public (read: White) awareness of social & civil rights. Throughout the course of his (officially, but not in total) 19 live albums, Pryor touched not just the subject of race; but amusingly & profanely tackled culture, politics, sexuality & drug use in a way that completely captured an all-too-unheard-from demographic. You can say he found a way to expand and improve upon Bill Cosby’s live act – with many, many more F and N words.
Pryor’s fame as a stand-up was parallel to his success in cinema – he appeared in over 40 films between the years of 1967-1997. Starring in, supporting or writing classics like “Silver Streak”, “Blue Collar”, “The Toy”, “Superman III” (and an often on-screen pairing with Gene Wilder) helped attain mainstream attention, earning himself a diversely massive fan base. Both during & after his life, Pryor (and the Pryor estate) was awarded an Emmy, 5 Grammys, 2 American Academy of Humor Awards, a Writer’s Guild Award & several Life-Time Achievements. Suffering from lifelong heart problems & multiple sclerosis, Pryor passed away in 2005 at the age of 65.
THAT’S FACTED UP: Sheridan Road in Peoria, IL (Pryor’s hometown) was renamed to Richard Pryor Place in 2002.
NOTABLE QUOTABLE: “When I was in Africa, this voice came to me and said, ‘Richard, what do you see?’ I said, ‘I see all types of people.’ The voice said, ‘But do you see any niggers?’ I said, ‘No.’ It said, ‘Do you know why? ‘Cause there aren’t any.’”
- #2 - Bill Hicks
Counter-culture’s most pertinent voice, Bill Hicks took the microphone like a sword and the stage like his horse. Hot-tempered, politically incorrect & irreverent to the bone – Hicks barked prophetic genius to unsuspecting audiences everywhere. Leaving nothing taboo; Hicks tore into religion, politics, consumerism, drug opponents and basically anything stigmatized – with fury. Contempt for culture and superficiality have never been criticized so lucidly by anyone since.
Starting his live career in the early 80′s, Hicks’ controversial social commentary was the subject of extreme censorship battles – but by 1990, his audience had significantly grown. Striking a friendship with alternative band Tool, he joined the 1992 Lollapalooza tour, opening their shows. His comedic impact can be seen on most modern comics, but more notably, musicians – with names like Radiohead, SPA, Super Furry Animals and Tool immortalizing him either in song or on album artwork. Hicks was diagnosed with pancreatic cancer in 1993, tragically passing away at home in 1994 at the age of 32. His iconic and prolific performances are regarded as some of comedy’s finest moments.
THAT’S FACTED UP: In 1993, comedian Denis Leary (then close friend of Bill) took a significant amount of Hicks’ previously recorded material – line for line – and recorded it as his own on his 1993 special “No Cure For Cancer”. The incident caused an abrupt ending to their friendship. When asked about the matter in an interview, Hicks said, “I have a scoop for you. I stole his act. I camouflaged it with punchlines, and, to really throw people off, I did it before he did.”
NOTABLE QUOTABLE: “It’s all about money, not freedom, okay? Nothing to do with fucking freedom. If you think you’re free, try going somewhere without fucking money, okay?”
- #1 – George Carlin
The one and only George Carlin – master of human condition & singular comedy icon of the 21st Century. A Carlin show was not just a comedy set – it was a lecture. A lecture from a professor dead-set on teaching you everything parents & authority didn’t cover. Astronomically intelligent and devoid of any sugar-coating, Carlin’s act was a lightning-fast account of every aspect of life. His wildly controversial, yet instantly accessible finesse found a place in society that most comics can only covet: wholly independent thought on a mainstream level of success.
Carlin first reached the public eye in the 1960′s on both The Ed Sullivan Show & The Tonight Show with Johnny Carson. Shedding his clean-cut, inoffensive image on-stage by the 70′s, he began to develop his unique styling – dividing his material into 3 categories (as described by Carlin himself): ”the little world” (observational humor), “the big world” (social commentary), and the “peculiarities of the English language”. Carlin was able to articulate hyper-detailed evaluation like an over-clocked computer – frequently using fast-paced, alliterated lists to punctuate his point. In 1978, his “Seven Dirty Words” routine was responsible for one of the biggest cases in censorship & broadcast history – a 5-4 win allowed the government to regulate “indecent material on the public airwaves”. Appearing in 14 films and 20 television shows, Carlin continued his show business career off the stage as well – ironically including the ‘Mr. Conductor’ character on children’s show “Shining Time Station” (!). Carlin has been awarded 5 Grammy Awards (among several others) for his 14 HBO specials, 19 albums and 5 books. Infinitely unique & completely unprecedented, George Carlin enjoyed over 50 successful years in show business before passing away in 2008 at the age of 71.
THAT’S FACTED UP: Carlin was the first-ever host of “Saturday Night Live”.
NOTABLE QUOTABLE: “The reason they call it the American Dream is because you have to be asleep to believe it.”