35. Mike Nichols and Elaine May
An Evening With Mike Nichols and Elaine May (1960)
"Alternative" comedy from an era when anything slightly to the left of Ozzie Nelson's starched suit jacket was considered out-there, Mike Nichols and Elaine May were a surprise mainstream hit that lit up Broadway, earned a Grammy, and found their way into millions of pretty starchy American homes. Nichols and May looked like nice enough kids and struck a chord with a lot of other bright young things who wondered why they couldn't just be honest (and funny) about their families and their relationships, at a time when honesty was kept behind closed doors. More playful and less political than the humorists of the day, but weirdly more subversive for their scrim of button-down respectability. JESS HARVELL
34. Redd Foxx
Foxx was the godfather of "blue" humor, taking frank sex talk out of the clubs and into American living rooms on dozens of his gleefully profane "party records." That wasn't all of Foxx, though, and Uncensored is a document of the don't-give-a-fuck freedom that African-American comedians were exploring in the'70s, where politics and anger bounced against unrepentant ribaldry and old-fashioned yuks. Recorded during Foxx's post-Sanford & Son transition from "adults only" icon to beloved institution, and lo-fi enough to make you feel like you're listening to someone's private bootleg of a particularly classic club set, Uncensored plays out like The Many Moods of Redd Foxx: a little funky nastiness, some plain silliness, and a lot of wry ruminating on America as it was then (and still is sometimes today). J.H.
33. Stan Freberg
The Very Best Of (1998)
More than a comedian, Freberg was an author, musician, voice actor, puppeteer and, yes, even ad man. The multi-talented Freberg wore all of those hats starting in the late '40s (and still wears them today) and this smartly compiled hodgepodge naturally runs the gamut between song parodies and sketches, hitting Tin Pan Alley, Broadway, Elvis, vaudeville, and plain nonsense with razor-sharp chops. When radio was king and television was in its infancy, Freberg was the right man at the right time, a flawless mixture of variety showmanship, theater-of-the-mind scene-building, and childlike silliness. H.O.
32. Dick Gregory
In Living Black & White (1961)
If you had to point to one comedian who had the TNT that blasted down the door for Foxx, Pryor, Murphy, Rock, Chappelle and, er, Sinbad, that man would be Dick Gregory. In a time when comedy was as segregated as the clubs that hosted comedians, the politically charged Gregory shared stages with Lenny Bruce and inspired George Carlin's future direction. An inspiring document of Gregory's everyman hard-thinking, this set at the Playboy Club in Chicago skewers the duplicitous media for calling him the "black Mort Sahl," continues on about JFK (calling him "my president" in present tense), and discusses his newly inherited right to vote. Possibly the comedy equivalent of the "I Have A Dream" speech. H.O.
31. Sam Kinison
Louder than Hell (1986)
On which the most notorious fallen Pentecostal preacher of the '80s (save Jimmy Swaggart) pokes holes in the story of Jesus's resurrection, critiques Charles Manson's logic, and wails like he's already roasting in Hell... which he figures won't be half as bad as the institution of marriage. His eventual forays into novelty-metal seemed redundant because he was already a rock star, with enough cackling, demonic charisma to make repugnant ideas funny, even compelling. Axl Rose circa "One in a Million," let's say, but with a sense of irony and a brain. A.P