He is the creator and executive producer of the Emmy Award-winning television series Monk on the USA Network and is co-host of WFMU radio's long-running conceptual comedy program Seven Second Delay.

One of his most well-known vignettes was a Saturday Night Live sketch called "White Like Me" (which he also directed), in which Eddie Murphy disguises himself as a Caucasian for a day.

Breckman told New Jersey Monthly that he was a voracious reader of the works of Arthur Conan Doyle, John D. MacDonald, and other authors of “solvable” mysteries, as well as being a big fan of the TV series Columbo.

About the series, Breckman said, "Many cop shows feature dark and provocative material: psycho-sexual killers, twisted, grim, flawed detectives.

"[3] In October 2018, TBS announced it would be launching a new TV series, The Misery Index, starring members of the Tenderloins comedy troupe, based on Breckman's card game, "Shit Happens".

[8] Breckman lives in Madison, New Jersey with his wife, documentary filmmaker Beth Landau, whom he met on the dating pages of Nerve.com and who is nicknamed "Boo.

The premise of the program seems to be a never-ending series of dead-on-arrival concepts, with the comedic value hinging on Breckman's recurring acknowledgment of failure and his desire to go home as quickly as possible.

Breckman has described his co-host as "a sad, bitter little man and WFMU's fundraisers are a good time to humiliate him and exploit his willingness to do just about anything, including prostituting himself, to raise money for his adorable little public hippy noise radio station."

Guests on the program included Dick Cavett, Joe Franklin, Amy Sedaris, Peter Stampfel, Jules Feiffer, Andrew VanWyngarden (of the band MGMT), Dan Okrent, Nora Ephron, Wallace Shawn, Jim Downey, and numerous other celebrities.

[14] Early in his singing career, Breckman was given the opportunity to perform as opening act for "American Pie" singer Don McLean, with whom he shared management.