Obi-Wan Kenobi
While the 80s were mostly a depressing time for him, he has tried to get more versed in the culture than he was at the time. He starts off with drinking wine, but ends up with a few Valley Girls and is quite drunk without meaning to. Yes, he could filter it but he's not interested in that tonight since there doesn't seem to be any danger at the moment.
He is hesitant to sing until he starts getting more alcohol, and then he sings Fast Car, Just like heaven, and if goaded into it could do Like a Virgin or Like a Prayer digging deep on Madonna there.