Twice with cars and alcohol.
I tore up the under carriage of my 67 2-door Chevy Impala because I was stupid drunk and I did a Dukes of Hazard turn jumping over something(still don't know what it was I hit). It was a Sunday night and no cops were on the interstate so I drove my car home as fast as it would go(20mph). I had to sell it because it never worked right after that.
Almost got a DUI because I let someone who I thought was less drunk than me drive my car, but he got reckless on a 2 lane country road with ditches on both sides(while it was raining). He ran my 2000 Buick custom(that I was making payments on)into a ditch and then fled the scene. I fled the scene to but some CAC called the police on me, so I had to talk my way out of it while a CAC pig was f**king with me. After that incident, I slowed down my drinking(25 years old)and now I have completely given up drinking(gave it up about 2 years ago).