"Killin' Them Softly," Dave Chappelle (2000)
OK, right off the bat, there could be some controversy because this technically was an HBO special. However, I feel morally obligated to include it because that's just how hilarious and influential it was/is. It was the precursor to the comedian's groundbreaking and unfortunately short-lived "Chappelle's Show" and helped launch him into the ranks of other superstar black comics like Chris Rock.
Featured clip: Dave speaks the truth on what "Sesame Street" is really teaching our children.
"Shut Up You F'ing Baby," David Cross (2002)
You get not one but two discs of ranting, raving and ridiculous anecdotes from half of the "Mr. Show" braintrust and the man who brought Tobias Funke to life. He spends a solid chunk of time talking about New York City, and specifically what it was like in NYC in the days and weeks immediately following 9/11. Believe me when I say that you won't even feel bad about laughing about post-9/11 jokes because his stories come from a genuine place and seem to hit on every chord.
Featured clip: David lets us know how he feels about morning radio DJs.
"Conversations with Inanimate Objects," Gary Gulman (2004)
In 2004, I went to see a "Tourgasm" stop in Ames, Iowa. (Yeah, yeah, don't judge.) The headliner was Dane Cook, but his opener, a 6-foot-6 Jewish dude who some people might remember from "Last Comic Standing," absolutely blew the doors off Stephens Auditorium. The next day, I ordered this CD online and began spreading it to the masses. I think he cusses once in the entire 60 minutes -- a rare feat these days -- and riffs on sugar cookies, Pepsi and walruses, among others. Also, Gary Gulman is single-handedly responsible for my obsession with anthropomorphizing everything in sight.
Featured clip: Gary picks a fight with sugar cookies.
"Feelin' Kinda Patton," Patton Oswalt (2004)
Before he voiced Remy in "Ratatouille," Oswalt voiced his opinions on G.W. Bush and Stella Dora Breakfast Treats in this acidically addictive set. Hands down, he comes up with the best analogies of any comedian -- most of which are definitely NSFW.
Featured clip: Patton drops some midget knowledge.
"My Secret Public Journal Live," Mike Birbiglia (2007)
He's pudgy and awkward -- or pawkward, as he says -- and the man knows how to tell a good story. He named this CD after his blog, Mike Birbiglia's Secret Public Journal, which itself is must-read material. A follow-up to the also hilarious "Two Drink Mike," Birbiglia seems to have come into his own as a storyteller with this set that details anecdotes ranging from his childhood to his burgeoning stand-up career.
Featured clip: Mike takes us on a trip down memory lane to Old Mill Pond.