In fact, it is that later event (the sleeping Rastafarian) that really makes the show itself enjoyable (which is really a shame considering the event wasn't planned and wasn't a part of his act). Towards the end of the show, Giraldo points out to the audience a man who is asleep, and while his buddy next to him quickly wakes him up, Giraldo doesn't let that stop him for messing up his mojo. Quickly dropping into a Jamaican accent, he goes through a whirlwind of stereotypical jokes, but ends on a story about his own trip to the tropical island where he gets on a glass-bottom boat. This really was the highlight of the event, and like I said, that's a shame since it is a complete tangent to whatever he was planning on covering.
As for the rest of his show, Giraldo's focus (as you might be able to guess from the DVD's title) is covers everything from gay marriage (as well as some gay bestiality involving kangaroos and koalas), to the belief that you should only start drinking when you're old and need the beer goggles because "old people are ugly," to steroid and drug use in sports figures (particularly Olympic Swimmer, Michael Phelps).
Giraldo's early jokes talk about life in NYC and how unusual the collection of people are. He talks about seeing everything from a homeless acapella group to a bachelorette party taking place just after 9/11. But it isn't long before he talks about the last Presidential Election (focusing, of course, on Obama) and even getting a last few digs in at George W. Bush.
Greg Giraldo has been seen most recently in the series of Comedy Central Roasts, but he has been around a good bit longer than that (even if that is where most casual stand-up fans know him from). Included on the Midlife Vices DVD is the comedian's first Comedy Central Presents special from back in 2000 where he talks about the obesity epidemic, edible underwear, diets, the Taco Bell Chihuahua and even Who Wants To Be a Millionaire? (with Regis Philbin). The only other additional feature is an unaired pilot to (what appears to be) an unaired series called Adult Content that has Giraldo talking frankly about sexuality in America. Seeing as both of these additions to the Midlife Vices DVD clock in at just under a half hour, this particular special has a bit more added content than most Comedy Central stand-up DVDs.
While Giraldo isn't my favorite comedian, I did find the overall set amusing and I enjoyed pretty much the entire show. But unless you are a big fan of his shtick, I don't really see the need to watch Midlife Vices multiple times and can only really recommend this DVD as a rental.