The album contains the audio of Giraldo's first (and ultimately from his death) only one-hour special; filmed at the Union Square Theatre in New York City during June 2009 and aired on Comedy Central on August 16, 2009. Released to DVD by Comedy Central Home Entertainment on October 20, 2009.
Midlife Vices was subject to mixed reviews, receiving slight harsh comments from mainstream outlets such as Allmusic's David Jefferies who commented on Giraldo's performance saying it was a "slight step down from his excellent debut album, Good Day to Cross a River" while still speaking highly of his bravado claiming, " Midlife Vices is comedian Greg Giraldo in fine form, ranting and raving about despair and depravity" and "sometimes gross, and sometimes downright mean, but always funny with that cocksure, New York state of mind. On that front, Midlife Vices satisfies, and anyone who appreciates grisly humor or "Kangaroo F***ing" will be laughing." More comedy-depth type publications such as Punchline Magazine raved the album to high praise stating, "A great stand-up comedian will, after 45 minutes or so on stage, leave his audience spent— spent from laughing, spent from thinking, feeling. Midlife Vices does this masterfully." The same publication named Midlife Vices as its #1 comedy album of 2009.