Too many times to count. A couple were more memorable:

1. Got in a fight in 5th grade. I tripped a kid as we were running in from recess and he started throwing on me. I got him to the ground and in full mount and slapped him a bit. His mom was an administrator at the school so I had to sit in her office for a week while she glared at me.

A slate of proud punishments (not exactly detentions):

1. I stopped showing up to classes in high school except math and wood shop. When I would show up to other classes I'd arrive considerably late. I got called into the dean's office and talked him out of it by being comically pious as two aides in his office laughed along with him. I bowed as I left his office. A couple years after high school, I met one of the aides at a party who was like "do you remember that?! that was me!" I was so glum during that period I didn't realize she was coming onto me.
2. I flunked most of my classes sophomore year (save math and CAD) and got kicked off the baseball team.
3. I was slated to retake sophomore english in my junior year, but my reading comprehension scores were the highest in the class so the teacher convinced the department to let me take two junior english classes instead (which was awesome because I really liked the speech class they put me in).
4. I didn't graduate from high school, but that summer I entered an advanced math camp on a recommendation later from my math teacher. During the math camp, the Principal of my high school starting calling me threatening to conspire to have me kicked out of math camp if I didn't return to high school to graduate. I told him "I know you get paid based on how many of your students graduate, so if you want me to come back you'll let me finish math camp." (I had a older peer at the math camp that told me how it worked.)
5. I already wrote about the time I alcohol poisoned myself on my way to high school (a different high school than 1-4).

I don't talk to my sister as much as I'd like and I didn't really grow up with her, but she might've been more naughty than even I was. She got kicked out of high school all together and wound up attending a continuation high school which, at least where we lived, was primarily reserved for kids in gangs and stuff.

a friend taped me to a chair with tons of tape

Well worth detention it sounds like.