30. Eddie Izzard
Dress to Kill (1998)
Eddie Izzard grew up in Europe, “where the history comes from,” which is why he can get away with being more raconteur than traditional standup. Also why he can do an act in make-up, heels, and a sort of kimono/leather pantsuit. Ultimately, it’s not how he’s dressed that kills, it’s his performance that’s encyclopedic in scope and kaleidoscopic in spirit. The act is part Python, part Carlin, part BBC documentary, but still a wholly original way for one man — or “executive transvestite” — to entertain a crowd. STEVE CIABATTONI
29. Lily Tomlin
This is a Recording (1972)
Once upon a time, AT&T was an omniscient, omnipotent monopoly, and Tomlin’s Ernestine the Telephone Operator embodied its cruel power. At the height of Nixon-era paranoia, her snorted amusement at customers’ privacy concerns and her officious manner (“Is this the party to whom I am speaking?”) reminded us that the most faceless bureaucracies are staffed by ordinary, error-prone human beings just like you, me, and G. Gordon Liddy. In the age of Google Street View and the Patriot Act, that fact remains equally terrifying and reassuring. KEITH HARRIS
28. Neil Hamburger
Great Phone Calls (1992)
The prank phone call is the lowest of the lowbrow; but even the most debased art form occasionally churns out a masterpiece. Circulated anonymously for years before alt-comedy legend Neil Hamburger’s name was finally (and vaguely) attached, Great Phone Calls is the apex of telephonic pranking. No one has ever kept a straighter face or taken a premise further into the realms of the uncomfortable than the perpetrator(s) herein. Tormenting hapless call-center operators, vexed take-out joint proprietors, and customer-service victims of all stripes, the longer they hang on, the more it becomes a journey into the deadpan, surrealist, skin-crawling, and just plain creepy. J.H.
27. Robert Klein
Child Of The ’50s (1973)
Take the brainy observations of Woody Allen and the improvisational characters of Jonathan Winters, drape them in a tweed jacket and give it all an Ivy League education and you’ve got this ground-breaking debut. As far as the comedy class of ’73 is concerned, Klein was probably the least jokey, while keeping a unique lean towards the most boyish and silly. Multi-character on-air radio bits, topical monologues about politics and everyday life happenings in New York are the lion’s share of Klein’s most popular and best-selling album. H.O.
26. Monty Python’s Flying Circus
Another Monty Python Record (1971)
More famous bits were still to come, but Monty Python’s most biting satire appears on their second album. Here, classics like “The Spanish Inquisition” and “Spam” run second on a record dedicated to brutalizing middle-class cultural pablum. From the graffiti that adorns its fake Beethoven sleeve, to the BBC announcers whispering non sequiturs between tracks, to the Gumbys shouting Chekhov, to a sketch where a violinist boils in fat during a concert, Another Monty Python Record defaced British cultural pretensions and institutions so completely that it helped the group become an institution in its own right. And no one expected a Python institution. JESSICA SUAREZ