25. Dennis Miller
The Off-White Album (1988)
Sure, he became a grand-mal, war-pig douchenozzle after 9/11 -- as Miller himself might have put it, we haven't seen anybody transform into a hawk so cheesily since they cancelled Manimal, babe. But this live set is a reminder that, much like Dubya, Miller was funny before the towers fell: snide, literate, able to make the most obscurantist word-clusters imaginable ("some bizarre B.F. Skinner hoedown," "Ansel Adams on peyote buttons," "Sao Paulo north-slope trip-weed") land like actual punch lines. Why anybody thought that made him Monday Night Football material, we'll never know. A.P.
24. Bruce McCulloch
Shame-Based Man (1995)
It's a shame comedy albums are expected to make you laugh, because you may not even crack a smile at McCulloch's debut collection of wide-eyed monologues and humiliation-intensive songs. That's due to the Kids in the Hall member's semi-autistic delivery and second-person-directed narrative, deployed in the manner of his best-known KITH character Gavin, which allows him to speak truths with knowing naivete. No matter his subject (fat people, bored housewives, closeted traveling salesmen), the object always seems to be you and your loneliness. J.S.
23. Spinal Tap
This is Spinal Tap (1984)
A loving parody of bare-chested rocker excess, This is Spinal Tap's, winking jokes about slobbering horndogs and blasts of bombastic heavy metal hooks isn't all that different from, say, Licensed to Ill. The Tap braintrust simply strip-mined two decades of rock history for its most over-the-top bits and moldiest cliches, provoking belly laughs even when they were playing it straight. But while the band was smart enough to not take the genre's mythologizing bullshit seriously, Spinal Tap never feels contemptuous of the good stuff. Especially the druids. J.H.
22. National Lampoon
Radio Dinner (1972)
Decades before sketch comedy was everywhere all the time, there was National Lampoon the magazine, the live show, and this slab of weird, Negativland-style radio-as-comedy art bites, written by Lampoon savants Tony Henrda and Michael O'Donoghue. It's very early-'70s (opening bit "Deteriorata" is a perfect slash at once-iconic hippie poem "Desiderata"), but it contains the roots of Saturday Night Live and therefore most humor that came after. Jokes ranged from tasteless-beyond-tasteless one liners ("Nagasaki: the art of Japanese body arrangement") to a parody of John Lennon so spot on it reminds you he wasn't always a deity by default. JOE GROSS
21. Chris Rock
Bigger & Blacker (1999)
Rock's hip-hop affinities may be somewhat cosmetic: Pen & Pixel album cover, Prince Paul-produced skits, Ol' Dirty Bastard cameos, fascination with titty bars. But they allow him to escape the just-another-live-standup-album trap. Bits from his HBO special that mock post-Columbine hysteria ("What the fuck was Hitler listening to?") and justify Bill Clinton's infidelity ("A man is as faithful as his options") are sharpened by proximity to the "Everybody's Free (To Wear Sunscreen)" takeoff "No Sex (In the Champagne Room)" and a Biz Markie "Brown Sugar" takedown that lusts after "white bitches" — including Meryl Streep. K.H.