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][2][9][10][11][12] 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][2][10][13]
Friedlander has performed stand-up comedy regularly throughout his entertainment career.[2][3][12] He continued to perform stand-up several nights a week in New York City while working on the sitcom 30 Rock.[2][3] Friedlander has stated that he is most relaxed when doing stand-up[10] and that he considers stand-up to be his first true love,[19] preferring it to acting.[20] He stated in 2012 that stand-up comedy is "still the most important thing I do from an artistic standpoint."[21]
Friedlander's comedic performances often feature him making outrageous and bombastic claims about himself with a deadpan delivery.[2][5][11][19] 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.[5][9][10][14][16]
One of his claims include being an expert in karate, having achieved an "extra-dark black belt" in the sport.[3][13][23] In 2010, he authored the humor book How to Beat Up Anybody: An Instructional and Inspirational Karate Book by the World Champion.[7][16] Friedlander's claims provide comedic irony when contrasted against his nonchalant attitude and physical appearance.[2][9] Friedlander wears large, thick-rimmed glasses, is often unshaven and is generally unkempt.[2][4][16]
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.[13][16] Frank is however much lazier than Friedlander's "World Champion" persona.[13][24]
In 2007, Heeb magazine included Friedlander in their list of "100 people you need to know about".[25]
His first Netflix special, America is the Greatest Country in the United States(2017), stitches together his shorter performances, mostly performed at the Comedy Cellar in Greenwich Village, to put his talents on best display.[26][27]
Friedlander was a regular cast member of the sitcom 30 Rock throughout its entire run, from October 11, 2006, to January 31, 2013.[1][22] His character, Frank Rossitano, is a sarcastic and wisecracking writer on the fictional show TGS with Tracy Jordan[1][10][30] Frank is lazy, slovenly, and lives with his mother (played by Patti Lupone).[16][31] He is also sex-obsessed, which he often reveals by way of vulgar and sexually suggestive comments.[1][16][30] Friedlander has stated that Frank Rossitano is based on at least two writers with whom Tina Fey used to work at Saturday Night Live.[30] His ever-changing, slogan-bearing trucker hats also became a running gag on the show.[20][30] 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.[11][17][30]
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.[33]
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.[5][11][12] Friedlander was recognized for his "hug guy" role for years after appearing in the video, causing complete strangers to offer him hugs.[5] The same year, he appeared in the comedy film Wet Hot American Summer.[1]
Friedlander has lived in the New York City area for most of his career, with the exception of two years spent in Los Angeles.[3] Currently residing in Queens,[10][21] he has stated that he prefers living in New York.[3]
Friedlander enjoys playing table tennis.[3][4][10][14] As a child, Friedlander had played the sport competitively; he took it up again in 2008.[3][4] 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.[36]