Friedlander has performed stand-up comedy regularly throughout his entertainment career. He continued to perform stand-up several nights a week in New York City while working on the sitcom 30 Rock.
Friedlander's comedic performances often feature him making outrageous and bombastic claims about himself with a deadpan delivery. Many of these claims are reflected in slogans displayed on the many trucker hats he wears - the most common being "World Champion", a slogan he has worn in various languages.