Released in 1959, this album captures the underground comedians at their early best and manages to both lampoon and accurately encapsulate the difference between hip and square society at the time. Unlike other mean-spirited comedy takes on the beatnik craze (Allan Sherman's "The Rebel" springs to mind), Close and Brent's satire was close to the truth because they truly were bohemian spirits. John Brent wrote poetry and honed his "Geets Romo" character (also known as "Huey the Hipster") while acting in a Jules Feiffer play. Del Close was an actor and poetry director at the Gaslight. And they both became well-known as being early members of Chicago's Second City.

Even though Del Close plays the square reporter on How To Speak Hip, he went on to live one of the most exciting (and hyperbolic) lives in comedy history. He befriended, worked with, and quite often did copious amounts of drugs with the likes of Lenny Bruce, Wavy Gravy, Frank Zappa, Tiny Tim, the Grateful Dead, and the Merry Pranksters. Hear the album here: