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 has stated that he is most relaxed when doing stand-up and that he considers stand-up to be his first true love, preferring it to acting. He stated in 2012 that stand-up comedy is “still the most important thing I do from an artistic standpoint.”
Friedlander has cited comedians Steven Wright, Sam Kinison and John Mulrooney as influences. He also says that Dave Attell is one of his favorite comics.
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.
One of his claims include being an expert in karate, having achieved an “extra-dark black belt” in the sport. In 2010, he authored the humor book How to Beat Up Anybody: An Instructional and Inspirational Karate Book by the World Champion. Friedlander’s claims provide comedic irony when contrasted against his nonchalant attitude and physical appearance. Friedlander wears large, thick-rimmed glasses, is often unshaven and is generally unkempt. His physique has also been described as “doughy”.
The look that Friedlander employs during his stand-up has also carried over into some of his television and film roles, including his 30 Rock role as TV writer Frank Rossitano. Frank is however much lazier than Friedlander’s “World Champion” persona.
In 2007, Heeb magazine included Friedlander in their list of “100 people you need to know about”.