Since pretty much every choice in this game is from a list, my friends and I have been messing around with randomization of Apocalypse World games. So far, we've done it twice. (Using random.org for random number generation)
The first time, I ran it for two players. I laid out all the playbooks and had them each choose up to two playbooks they didn't want to play, then choose randomly from the rest. Then we chose names randomly, looks randomly, stats randomly, starting moves randomly, and starting gear. Randomly. They asked, what's the climate like? So I rolled some fudge dice and got -3. "Fucking cold". Turned out Heron the Skinner's random art of making fur and leather clothes was an awesome choice! Then we played a session; it was pretty cool.
The second time, another player ran it for me and someone else, and we followed the same path, only randomizing even more stuff. We chose a random latitude and longitude (wound up in Suriname) and did fudge dice for random climate again (+3). This time, though, not only did we randomly generate our characters, we chose random Hx options, random highlighting of stats, and every improvement we chose was chosen randomly! (Throwing out the options at each step that were mechanically terrible; e.g. replace a stat with a worse stat)
Wound up with some seriously interesting characters, though it might have just been that we were very drunk. I had a Brainer whose first advancement was, randomly, "take a move from another playbook" and wound up with Reputation. Pretty sweet!