I think you randomized the crosshair on the joke a bit poorly, it can be too slow sometimes. It got so slow that it took around 3-4 minutes to reach the center of the target. I also got Vinny as a guest as my first encounter and his Speen line kept reappearing in dialogue even after the encounter was over, while Leno was making jokes in front of a crowd. Then my second encounter was Vinny again and this time the "Today's guest: Vinny" screen got stuck on the screen.
Cute game overall though.