20. Firesign Theater
Don't Crush That Dwarf, Hand Me the Pliers (1970)
Like jazz musicians, comics prize the serendipity of the live performance. Not so this L.A. comedy troupe, who instead manipulated studio effects to create artifacts impossible to enact in real time, much like their acid-rock contemporaries. Ironically, they updated the old-time radio show format in the process. This album-length sketch, in which former child actor George Tirebiter endures a dystopian post-America by channel surfing past surreal TV commercials, game shows, and televangelist spiels to watch reruns of his old Pudgy and Mudhead movies, captures pothead dementia at its most fertile, profound, and spooky. K.H.
19. Louis C.K.
Chewed Up (2008)
Louis C.K.'s jokes about fatherhood are piercing, heartfelt, cathartically funny; he writes about being a parent like Bill Cosby blessed with Lenny Bruce's compulsion to say the unthinkable: Pretty sure the Cos never compared the contents of his daughter's diaper to "a 48-year-old alcoholic man's shit." But he's the standup every other standup wants to be right now because he writes that well about everything, approaching even the observational bits about deer or Cinnabons or underwear as opportunities for dangerous truth-telling. Pick hit: "I Enjoy Being White," as transgressive in its own way as onetime C.K. collaborator Chris Rock's routine about the two types of African-Americans. A.P.
18. Jonathan Winters
The Wonderful World of Jonathan Winters (1960)
Winters begins his debut LP by stating that he was tossed in a mental institution after announcing his true extraterrestrial origins. That anecdote might seem a zany comic's mere braggadocio, if not for the free-associative whirl that follows. His impersonation of Ohio hick Elwood P. Suggins and his expert dissections of TV western cliches are evident products of a hyperactive brain — you can hear how Winters' manic improvisatory style would later impact the motormouth coke-shtick of Robin Williams. Don't hold it against him. K.H.
17. "Weird Al" Yankovic
In 3-D (1984)
Before In 3-D, music's greatest parody artist still sounded like he was cranking out basement demos, an accordion-spill of low-budget sound, creatively cobbled arrangements, and jokes your goony pals might have suggested if you were a hell of a lot funnier. The not-as-difficult sophomore album, In 3-D was the birth of the true Al, a man who puts far more ambition and artistry than necessary into songs about sandwiches. With parodies that sounded (almost) as slick as their source material, In 3-D took Al mainstream: It's still hard to hear "Beat It" without unconsciously hearing the faint echo of "Eat It," a testament to Al's preternatural talent for reclaiming hooks and the pinpoint mimicry of his spookily precise band. J.H.
16. Mitch Hedberg
Strategic Grill Locations (1999)
Deep into Strategic Grill Locations, the laconic Hedberg laments that, as a comedian, he's also expected to act and write screenplays. He never got to do much of either before his death in 2005, but no one else ever got so close to standup's pure, raw ideal. You don't notice that perfection at first, since Hedberg spends much of his set announcing his mistakes and bad punchlines, but his economical one-liners ("I used to do drugs. I still do, but I used to, too") make up for any sloppy editing. The result is a messy, brilliant album that reflects the messy, brilliant Mitch. J.S.