Life Is Worth Losing was recorded simultaneously with the live broadcast of the HBO special of the same title, his thirteenth HBO stand-up comedy special, and was his final special recorded from the Beacon Theater. It is the first project Carlin had undertaken since completing drug rehabilitation in 2005.
Early on in the program, Carlin proudly announces that he was 341 days sober at the time of the recording, and that 2006 will be his 50th year in show business.
