I first saw this while on tour in 2001. We had about half of our crew quarantined in one hotel room, barfing the night away; the rest of us safe and healthy next door. We healthy few settled on this stand-up routine during a late night HBO showing. Chappelle wasn't yet the cultural phenomenon he would become four years later, thanks to his show on Comedy Central. I can't think of another DVD more commonly on people's shelves, this coming from a wanderer's POV. I've slept on more strangers' floors than I can keep track of, and I always peruse people's movie collections at some point; it's a nice conversation starter.
Anyway, we all went into this routine ready to switch the station. We knew Chappelle from supporting roles in Men in Tights, The Nutty Professor, and You've Got Mail, thus expecting nothing. Needless to say, we watched this in its entirety and laughed throughout... a lot. I can't think of a better glowing/speaking object to communally stare at and share than a great stand-up routine and this one, in my opinion, is the greatest. It solidified Chappelle as both a bizarre comic virtuoso and a celebrity worth rooting for. His comic style is prescient, strange, light, and unpredictable.
But I think at least half of a routine's success (probably much more) can be measured by the laughter it elicits. Laughter is subjective, but I don't know a single person who doesn't find a good portion of this funny. I also don't know of anyone who doesn't admire him both for his comedy and his trepidation for fame and fortune. He's not the loudest advocate in the room, but he's somehow saying more.
Chappelle is naturally funny, born for comedy. It's in his face, his voice, and his perception of the world and all of it's silly problems. He doesn't avoid touchy topics, but always approaches them with care. He's looser than most comedians, bits meld into each other carelessly but seamlessly. Killing Them Softly doesn't have the vibe of a script rehearsed ad nauseam, it's not tethered to narrative nor is it in a hurry to get somewhere or say something larger. And yet, it gets there and says a lot. I adore it.
Side note: the bit about his white friend, Chip, who races the police, is the most quoted standup bit amongst my group of friends.