OK, here's one.
One of our housemates ran into a buddy of his from HS that he hadn't seen in years, turns out the guy was a VT Trooper. So they got together and planned a little prank on us. One night we were heading back home from a night out in Burlington and just as we turned on to our road, WHAMO!! Cop lights start flashing
Immediately, without hesitation, all four windows in the car go down and we start chucking beers/weed out the window (obviously wouldn't do any good but hey we were drunk). Once we came to a stop and the trooper car pulls up behind us we see 2 cops get out. Next thing we know it's our buddy Ricky sticking his head in the window of the car yelling "GOTCHA"!!!!!! And the Trooper was laughing his balls off. Ricky said, hey guys meet Kevin, he's a VT State Trooper and a good buddy of mine from HS. We would've beat the shit out of Ricky for that but we were able to find our beers and bag so all was good
We still talk about that night to this day.