5. Patton Oswalt – Werewolves And Lollipops (2007)
In the comedy world, cynic laureate Patton Oswalt is our Biggie or Em figure, a new-school workaholic landing on the exact point where staggering chops don’t overshadow emotion. A former English major, every Patton line on this, his tightest set to date, seems like it was constructed on a granular level, each word picked over microscopically to find the most efficient way to take down KFC or George Lucas. This, of course, makes for astonishing moments, like when Oswalt freestyles a corrosive splatter poem taking the voice of an idiot heckler intent on ruining the recording: “When my body returns to the loam and the cities are but dustâ€¦ the Neuromancers walking the wastelands will carry high my standard of douchebaggery!” C.R.W.
4. George Carlin – Class Clown (1972)
In the early 1970s, when Carlin flipped from clean-cut club act to campus cult hero, he blazed a dual path of success and subversion. Starting by tickling that immature spot that makes us all giggle (farts, etc.), Carlin stealthily unmasks religious bullshit, punks the war machine, and ends on the legendary “Seven Words You Can Never Say on Television” (for which he was arrested that summer). Today it’s amazing how “un-dirty” it sounds, but it’s still the funniest first amendment closing argument of all time. Lenny Bruce may have skeched the blueprint, but Carlin was the master builder, a stunning verbal contortionist who endures today as comedy’s most eloquent motherfucker S.C.
3. Eddie Murphy – Comedian (1983)
While Murphy’s self-titled debut, released a year prior, is easily its equal in terms of material, Comedian is untouchable as a document of an artist’s supernova moment, arriving between Trading Places and Beverly Hills Cop. (At the time, the title scanned as a mastery of understatement, like Rolls-Royce: Car, yet he’s never released a comedy album since.) That this set considers a warning to “faggots” staring at his ass to be an icebreaker says as much about 1983 as it does Murphy (age: 22); and while the bit may not age well, the swagger does. Fifty minutes of pure star-power, grounded in humanity that would soon be swallowed and devoured by that leather suit. S.K.
A.k.a. “The One After Nearly Burning to Death After a Rum-Soaked, Freebasing-Related Likely Suicide Attempt.” Yet from sticky odes to fucking (“Women”) to “Prison” riffs (“Don’t fuck with the double Muslims”), hellish near-death only deepened Pryor’s singular rhythms. He famously asks his pipe permission to leave the room on “Freebase” and goes head-on into his accident (“You can really tell when you fucked up when the doctor goes, ‘AAAAAHHHH!'”). And it’s impossible not to tear up and crack up in equal measure as he relates his trip to Africa. He’s the king of ’em all. J.G.