Chris Elliott's involvement with David Letterman's show produced an array of colorful characters on both NBC and CBS. For me, his crowning achievements on the show were often the short films created to fill time between the guests.
Poolside Ecstasy, from 1994, is hilarious for content and it's uncanny ability to perfectly mimic the washed out vibe of a generic mid 80s porno. 1993's short The Traveling Poet teams Elliott with Paul Dooley and provides insight into a character type that Elliott would nurture further with 1994s Cabin Boy movie.
The Traveling Poet