I was such a goody two shoes as a kid and throughout high school. I saved dumb stunts up for later.
Absolute dumbest: I was 22. Lived in Omaha, but was up in DesMoines on a business trip that just happened to coincide with the Iowa State Fair on the night that Chicago was playing in a concert there. Met friends at the Fair after work, we wandered around the fair until time for the concert, had a couple of beers which I totally detested but was the only choice of adult beverage at the fair. We all went to the concert, and instead of leaving right after the concert, I stayed with friends and partied some more.
Drove back to Omaha at 2am after the bars closed, not only tired, but alone and slightly intoxicated. 144 miles to the far east side of Omaha and I lived on 96th.
At one point, I pulled over, took my contacts OUT (

) cause they were bugging me, and I followed a semi quite closely, because I could see his taillights. He was not happy. He pulled off the interstate, so I would go on ahead, and then came right back on. He passed me, and I kept following him all the way through Omaha.
Got home, went into my apartment, went to sleep for a couple of hours. When I got up in the morning I couldn't find my contacts. Found them laying on the console of my car.
Never did see a cop, the whole way home. But I must have had an army of Guardian Angels watching over me.
That stunt far surpassed stupid.