Comedy Central Presents: Nick DiPaolo

Nick Di Paolo builds his 2002 half-hour around the physical and mental irritation of getting older. He complains his way through the indignities of aging, focusing specifically on the granular, uncomfortable details of his first prostate exam. When he isn’t detailing his bodily decline, he shifts his aggravation toward early-2000s pop culture, spending a chunk of the set explaining exactly why The Sopranos resonates with him.

Filmed at the Hudson Theatre in New York City for the sixth season of the network’s flagship stand-up series, the 21-minute set caught Di Paolo as a working club comic making a jump to a broader cable audience. He was already an established, easily annoyed presence in the Northeast comedy scene. This tight showcase captures the baseline cynicism that would carry him into later hour-long specials and an Emmy-nominated writing stint on The Chris Rock Show.