If you hopped on the Dave Chappelle bandwagon only after his show on Comedy Central was hailed as genius by critics, then you seriously missed out on a back catalogue that consisted of hilarious standup specials, movie appearances and co-starring duties. Ever since witnessing his Ahchoo character in Mel Brooks’ Robin Hood: Men in Tights, put a beating on hold so he could squeeze some air into his Reeboks Pumps, it was evident that this dude was bound to make his mark in the comedy genre. But it wasn’t until he released Half Baked, and gave life to Thurgood Jenkins, that audiences really started taking notice of what this blue chip prospect brought to the game.

Gifted with a talent for taking everyday curveball situations and hitting them out the park for the sake of humor, D.C. from Washington D.C. knows how to tickle people’s souls. This scene from Half Baked is the perfect example of an embarrassing everyday situation that Dave turned into gold (Gold, Jerry! Gold!). They say that the brokest men are the most romantic, right? I mean, it’s no surprise that 99 Cent stores in the hood (where else would they be?) are packed to the brim with men shopping on Valentine’s Day.

 

 

Faking it till you make it, is a way of life in some cultures, and Chappelle’s character doesn’t just seem to be a student of the philosophy—he’s probably added a chapter or two to the scriptures. Starting off with a mere $8, he didn’t only demonstrate how to ball on a budget, he showed you how every cent was spent and how to fake the funk while spending it. You can’t be blatantly cheap; there’s an art to it. A style you have to front if you want to come across as romantic, yet, adorably broke.

Transportation? Why waste a beautiful day for a stroll in a cab? Let’s take a three-hour walk and get to know each other. Hungry? Here’s a hotdog. Whatever you have to do to keep the good times going, and your chances of consummation at a high rate while walking around with rabbit ears, you do it and run with it.

Whether or not you co-sign the methods this man used to get by, you know that It takes a certain kind of cat to front like he’s this thoughtful. He steals from the penniless and lies about his way of life in order to ensure a visit to the fountain of youth. Even when a greedy hotdog vendor bled him for an extra dollar, Dave kept his composure (kind of) and played it cooler than Yeti. Say what you will about the mischievous techniques Dave uses to stretch a buck, but you can’t help but respect the lengths he’d go through to be the ideal date. It’s better than one of those “let’s split the bill” boys, or even worse, “you got this?” birds that try to live off of working women. Only a man dedicated to putting something in a woman’s stomach (double meaning) would steal $3.18 from a homeless man to make that happen, and with that final act, take the phrase, “by any means necessary” to an entirely new comedic level. Not only was it understandable, it was damn near admirable. Dave Chappelle, where art thou?