Richard Pryor -- Jimi Hendrix
The average guitarist will quote Jimi Hendrix as being the very best. The serious comedy fan will often pick Pryor as being the very best. Both are known for innovating an industry, as well as some outrageous substance abuse. Hendrix's infamy was for soaking a bandanna in LSD so that the drug would enter his pores during his performance; Pryor's for setting himself on fire while free-basing cocaine. Both died prematurely. Age 65 was not a bad run for Pryor all things considered, the heart problems that caught up with him are probably not entirely unrelated to his drug use. And Hendrix's notorious drug overdose and subsequent asphyxiation is one of the reigning rock-star deaths in the halls of entertainer mortality. They both inspired a generation, and led quintessential rock-star lives.
George Carlin -- John Lennon
Also known for inspiring a generation, these two men are just about the biggest heroes existing in their respective fields. These philosopher-poets, are known for periods of angry and political creativity. They're both prolific. Lennon had 13 albums if you only count his solo-work. Carlin released 19 comedy albums. Virtually everybody who came after them cites them as an inspiration.
Lenny Bruce -- Bob Dylan
Bill Cosby -- B.B. King
These larger than life masters are decorated performers, champions of philanthropy and veritable African American folk heroes. While King is the living king of blues, Cosby is a living legend from standup comedy's dawn. Plus, Cosby's unique drawl is not unlike a minor third getting pulled in a nice slow mid-register blues scale. Right? [editor's note: this was written in 2010]
Woodie Allen -- Paul Simon
The archetypal New York Jewish intellectuals, these auteurs of the 60's, 70's, 80's and henceforth rarely take breaks from producing comedy or touring pop music. They are both known for producing culturally reflective works for the respective decade, and are celebrated most highly for their early work, post-hippie and New York City themes.
Bill Hicks -- Jim MorrisonCelebrated for being more or less the farthest 'out there on the edge' among the larger-than-life comedy and rock stars, these party-poets have a reputation for battling with censorship, as well as doing anything necessary to experiment with their 'doors of perception'. They valued integrity and were often criticized by the mainstream for keeping it too real on stage. Vulgarity, drugs, and a somewhat aggressive message for peace and goodwill tie these two legends, and tragic deaths during the primes of their careers unite their destinies as patron saints of self-destructive artists everywhere.
Mike Birbiglia -- Bruce SpringsteenEveryman personalities with endless talent for story-telling, these east-coast heavyweights appeal to crowds with likability, charisma, and good old-fashioned writing chops. Their timeline isn't exactly synchronous, but their occasionally political campfire styles and--going out on a limb slightly on Birbig's behalf--inevitable sharing of A-list fame makes them suitable brethren in the comedy-rock multiverse.
Dane Cook -- James Hetfield
If there is heavy metal in comedy, and it can be characterized by loud speedy riffs, then Dane Cook is the Metallica of stand-up. These former gods lost a lot of their original fan-bass during the 2000's with cheesed-out contrivances, but they still reign supreme in terms of career record sales, household-name-sake, and undeniable hero-worship amongst a new generation of metal bands and comedians. In addition to big arena antics and over-the top personalities, they have a very similar career arch: Harmful If Swallowed is Ride the Lightening, they hold up as seminal and (dare I say?) ground-breaking works... the Comedy Central Presents special is the Black Album, which was the last essentially decent product which due to pop-cultural over-saturation, was clearly the toppling point into commercialized ruination. Vicious Circle was St. Anger... yikes. [editor's note: It's 2016 and the new Metallica album is surprisingly awesome.]
Dave Chappelle -- PrinceNeither of these performers are most famous for they're best skill. Prince is best well known as a sex-drenched singer, and Chappelle is best recognized for his funny impersonations on his (Chappelle's) show. However, it hasn't always been commonly known that these men are standup-comic and technical guitar virtuosos. Chappelle's standup specials are among the best of the late 90's / early oughts and Prince's innovative guitar playing has been called by Eric Clapton one of his top five favorites. They both paid their dues with one talent and then earned millions on something else.
Doug Stanhope -- Tom WaitsThese anti-commercialization troubadours are sub-culture icons with a knack for chain-smoking, uncomfortable stories about all kinds of binges, and sometimes complete disregard for performance convention of any kind. Perhaps challenging the Hicks/Morrison duo for most 'out-there on the edge-ness', they are not just known for chemical mood alteration but also for emotional health concerns and disconcerting intellectual priorities. The exciting thing is they're still alive and kicking, and seem to have developed some sort of equilibrium with the world around them. Also, their work seems to attract the same types of people.
Mitch Hedberg -- Kurt Cobain
These men can be credited with almost single-handedly creating a renewal of popular interest in standup comedy and hard rock. While grunge was a reinvention of mainstream-accessible heavy music, Hedberg's popularity practically began what some are calling the second comedy boom. Failed drug battles and tragic deaths at the height of their popularity are just the unfortunate icing on otherwise industry-changing cakes.
Maria Bamford -- BjorkWhat more needs to be said about these odd, risk-taking ladies other than: Good for them for proving that men aren't the only people who can turn batshit crazy into successful careers. Before they came around, ladies needed to be either sexy vixens or big strong matriarch types. These wonderful freaks are neither and proved that women could achieve and maintain a strong presence on the male-dominated nerd market using weirdness and strong writing alone.
Marc Maron -- Beck Hanson
Jerry Seinfeld -- Chris CornellThese early 90's icons were at the right place at the right time to enjoy huge mainstream success, but are struggling to re-invent their careers in the 2000s. As standup audiences are getting younger, Seinfeld is losing relevance, and is clinging to his original fans--now married 40 somethings--with projects like, "The Marriage Ref". Cornell, who enjoyed a pretty successful run with the former members of Rage Against the Machine in the super-group Audioslave, would love to forget his latest efforts with producer Timbaland, and has yet to out-do his creative output during the days of Temple of the Dog and Soundgarden. They're once-great masters who are still young enough to make magic happen again.
Patton Oswalt --Thom YorkIf any man can be called the Radiohead of Comedy, it is Patton Oswalt. Thom York and Patton Oswalt Share similar artistic pathways from Great to Better to Amazing to "What's Trail's Left to Blaze--I guess I'll have fun just being myself for the next decade." They showed that comedy and rock music can sound similar to the classics in delivery but still come from completely unheard-of places emotionally and conceptually. The sheer power of expression for these guys to transmit an idea to the brain is somewhere on the level of literary giants like Orwell, Keroac, Palahniuk, Vonnegut, etc. And they also share that flair for the dystopian to boot.
Chris Rock -- Michael JacksonEven though Chris Rock wasn't part of the 'original kings of comedy' tour, I think it's self-evident that Chris Rock is just as much the King of Comedy as Michael Jackson was the King of Pop. These superstars managed to be the best there was at what they did during the height of their power, with hardly anyone in the rear-view worth footnoting. They also are infamously questionable role-models--Jackson for obvious reasons--and Rock both for controversial language use as well as publishing in his memoirs about the unfair double-standard that black entertainers are demanded to set a good example. Although, not wanting to set a good example is not quite the same as actually setting a bad example, and in this regard--as well as in monumental career achievements--Jackson wins out.
Sara Silverman -- Joan JettThese two sassy bad-asses managed to be standout women during respective era's when males dominated their industries (as they still do, generally speaking). But when female singers were usually more famous for pop music than Rock, and female funny-ladies were more famous for acting than stand-up, these two stayed true to their roots, earning glory for the fundamentals. Also, for better or worse, they have undercurrent reputations for benefiting from personal relationships they've had with people in the industry. However, they are both generally regarded as talented and not undeserving of success.
Louis C.K. -- Van MorrisonProlific, transcendental, easily accessible by mainstream America, worshiped by creative folks... they have huge singles ("Brown Eye'd Girl" and "Moondance"... "Daddy, Why?" and "Best Technology for Worst Generation") as well as genius albums (Astral Weeks, Live in Huston). Van Morisson and Louis C.K. share a yearning for and reflection of the innocence of youth. They seem to use time on-stage as a search for redemption. Louis C.K.'s comedy is a man confronting his struggle with the paradoxes of modern adulthood. His jokes are fluid, contiguous, musically expressing shame, fear, wonder and--as Lester Bangs famously wrote about Morisson's Astral Weeks--"the great search, fueled by the belief that through these musical and mental processes, illumination is attainable, or at least may be glimpsed."
Zach Galifianakis -- Les ClaypoolThere is a similar experience when these two performers do their thing. For starters, fusion. I don't just mean the fusion of music and comedy, as Zach plays the piano and Les drops one-liners or sings some amusing songs. I mean that their styles are amalgamous and far-reaching within their own medium. Zach's unique delivery combines Stephen Wright nonsense with Michael Ian Black conceptualization. Les' bass-heavy music is part funk-metal, part jazz, part psychedelic polka. Additionally, improvisation is a heavy element of their shows, which further obscures their performances from categorical convention. Most importantly, these two share a strict sense of postmodernism. At no point in the show do we feel we know the performer personally, we are only given a facade of absurdity, which allows us to really sink our teeth into the meat of their craft without any personal context getting in the way. In this way, they are the opposite of Bruce and Birbigs, but still effective because mysteriousness can be just as engaging.
Demetri Martin -- Stephen Malkmus
Dave Attell ~~ Tom Morella
Sam Kinison -- Janice JoplinThey're known for their shrill screams, homely appearances, passionate performances, drug-use, tragic early death, and demigod roles during the points where their industries started turning psychedelic, personal, rebellious and WTF-inspiring.