Breckman was born in Philadelphia, Pennsylvania to a middle-class Jewish family. He grew up in Haddonfield, New Jersey and attended Haddonfield Memorial High School. Breckman dropped out of Boston University in his freshman year, and despite an admitted lack of musical ability, he launched a brief career as a satirical folk singer. He released two albums, Don't Get Killed and Proud Dad.

Breckman wrote for Late Night With David Letterman from 1982 to 1984, and contributed sketches to Saturday Night Live from 1983 to 1996. 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. In 2003, he took part in a USO tour to US military war zones, contributing material for comedian Al Franken. That year he was served as a jokewriter for comedian Steve Martin's stint as host of the Academy Awards.

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." They have two children. As an engagement present, Breckman applied his fiancee's name (spelled "Beth Landow") to the murder victim in Monk's season two (2003) premiere, Mr. Monk Goes Back to School.

Breckman has three children from a previous marriage. His brother David has worked on Monk in various producer roles.

Since 1992, Breckman and WFMU station manager Ken Freedman have co-hosted a weekly one-hour comedy call-in radio program, Seven Second Delay. 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 acknowledgement 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."

In 1998, Gadfly Records released Death-Defying Radio Stunts, a CD of outrageous moments from Seven Second Delay broadcasts.

In 2009, Seven Second Delay began monthly broadcasts from the Upright Citizens Brigade Theater, in Manhattan.

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. The two did not get along, and a feud developed, which has persisted to the present day. Breckman and McLean have penned competing renditions of the origins of their mutual dislike, both of which are available online.

Movies

• Moving (1988)
• On the Rocks (1988)
• Hot to Trot (1988)
• True Identity (1991)
• I.Q. (1994)
• Sgt. Bilko (1996)
• Rat Race (2001)

TV and video

• Hot Hero Sandwich (1979)
• Late Night with David Letterman (1982)
• Saturday Night Live (1983—1985)
• Tourist Trap (1998)
• TV Funhouse (2000)
• Monk (2002-2009)
• The 75th Annual Academy Awards (2003)