Friedlander is known for his distinctive look, which includes oversized glasses, shaggy hair, and a t-shirt and trucker hat (both often emblazoned with slogans such as "world champion"), and a generally unkempt appearance.[1][3][10][11][12][13] It is a look he maintains as a stand-up comedian, during most of his public appearances, and which he has employed in some of his acting roles.[1][3][11][14]
Friedlander has performed stand-up comedy regularly throughout his entertainment career.[3][4][13] He continued to perform stand-up several nights a week in New York City while working on the sitcom 30 Rock.[3][4] Friedlander has stated that he is most relaxed when doing stand-up[11] and that he considers stand-up to be his first true love,[20] preferring it to acting.[21] He stated in 2012 that stand-up comedy is "still the most important thing I do from an artistic standpoint."[22]
Friedlander's comedic performances often feature him making outrageous and bombastic claims about himself with a deadpan delivery.[3][6][12][20] 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.[6][10][11][15][17]
One of his claims include being an expert in karate, having achieved an "extra-dark black belt" in the sport.[4][14][24] In 2010, he authored the humor book How to Beat Up Anybody: An Instructional and Inspirational Karate Book by the World Champion.[8][17] Friedlander's claims provide comedic irony when contrasted against his nonchalant attitude and physical appearance.[3][10] Friedlander wears large, thick-rimmed glasses, is often unshaven and is generally unkempt.[3][5][17]
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.[14][17] Frank is however much lazier than Friedlander's "World Champion" persona.[14][25]
In 2007, Heeb magazine included Friedlander in their list of "100 people you need to know about".[26]
Friedlander was a regular cast member of the sitcom 30 Rock throughout its entire run, from October 11, 2006, to January 31, 2013.[1][23] His character, Frank Rossitano, is a sarcastic and wisecracking writer on the fictional show TGS with Tracy Jordan[1][11][29] Frank is lazy, slovenly, and lives with his mother (played by Patti Lupone).[17][30] He is also sex-obsessed, which he often reveals by way of vulgar and sexually suggestive comments.[1][17][29] Friedlander has stated that Frank Rossitano is based on at least two writers with whom Tina Fey used to work at Saturday Night Live.[29] His ever-changing, slogan-bearing trucker hats also became a running gag on the show.[21][29] Friedlander makes his hats himself and created enough of them to be able to wear a different one in each scene of 30 Rock, which is about three hats per show.[12][18][29]
In May and June 2014, Friedlander narrated ESPN's Inside: U.S. Soccer’s March to Brazil six-part series in preparation for the World Cup in Brazil.[32]
In 2001, Friedlander played "the hug guy" in the music video for the Dave Matthews Band single "Everyday"; his character is seen hugging various people throughout the video.[6][12][13] Friedlander was recognized for his "hug guy" role for years after appearing in the video, causing complete strangers to offer him hugs.[6] The same year, he appeared in the comedy film Wet Hot American Summer.[1][2]
Friedlander has lived in the New York City area for most of his career, with the exception of two years spent in Los Angeles.[4] Currently residing in Queens,[11][22] he has stated that he prefers living in New York.[4]
Friedlander enjoys playing table tennis.[4][5][11][15] As a child, he had played the sport competitively, and he took it up again in 2008.[4][5] He is a big fan of professional wrestling, which is often used as subject matter for his trademark hats and shirts. He is also a fan of the New York Red Bulls, has attended games at Red Bull Arena and appeared in commercials for the team.[35]