[5][6][7][8][9][10] Earlier in his career, he was recognized as "the hug guy" from the music video for the 2001 Dave Matthews Band single "Everyday".

[4][5][11] 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.

[22] Friedlander's comedic performances often feature him making outrageous and bombastic claims about himself with a deadpan delivery.

Over the 2000s Friedlander held guest roles on several television shows, including Spin City, Curb Your Enthusiasm and Flight of the Conchords, as well as providing voices for characters on the animated series Wonder Showzen and Xavier: Renegade Angel.Friedlander made regular appearances on the entertainment and pop-culture program Best Week Ever.

[8][19] He appeared as the online co-host of the 2009 TV Land Awards, alongside main stage host Neil Patrick Harris.

[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][16][28] Friedlander has stated that Frank Rossitano is based on at least two writers with whom Tina Fey used to work at Saturday Night Live.

[31] He has appeared on MSNBC's Last Word with Lawrence O'Donnell and provided personal commentary on The World Cup and soccer in general.

[1] In 2003 Friedlander played Toby Radloff in the biopic American Splendor, a role that received favorable reviews — his performance was deemed "unforgettable"[1] by The New York Times and "pitch-perfect" by both Nick A. Zaino III of The Boston Globe[8] and Dan Dinicola of The Daily Gazette.

[7][13] He has also appeared in films such as Duane Hopwood, Chapter 27, Southern Belles, Live Free or Die, and Feast.

[7] Friedlander has lived in the New York City area for most of his career, with the exception of two years spent in Los Angeles.