I'll bust out my second biggest night of drinking, then:
Santorini's, discounted drinks that night (I dunno why, could have been the size of the group, most of us were regulars, dunno). Started off with Balvenie 21YO. So I'd remember it. Sometime during the night I got a free (comped from Santo's) a 32oz blue Long Island. GAD, but it was free, and I was sailin' at the time. $300 bar bill for my bro (who had about one drink per hour, since he was DD), my buddy, and me. My buddy and I, for the last 3 hours of the bar part of the night, had Jack shots delivered every 20 minutes or so, in addition to the VT's I was having.
The three of us went back to my apt for an afterbar, and killed 2 liters of booze, a twelver, and when the sun rose, we finally decided that we needed to crash, if only because we all worked the next day.
That's a night I won't do again. Unless MN wins the F4 in Mpls soon........