I have two:
1. At my high school, I still hold the record for most hit-by-pitches in a season (42) and in a career (140). We averaged 30-35 games per season, so better than one per game. I played 1st base, started all 4 years, and my "thing" was that on any pickoff attempt to first I would smash the tag onto the runner HARD. I dunno why I did it, it started off to be funny I guess. My goal was to pop the runner in the back of the head and make their helmet pop off if they dove back to the bag. This earned me lots of hate from opposing teams, so I got plunked on purpose a ton. It got to the point that if we were the visitor, I'd get plunked in the 1st inning before I'd even taken the field because the other team knew me. I'd get warned by the umpire at least every game, but I learned how to do it hard, but not look malicious, and never enough to get ejected.
2. Pretty sure I still hold the record for most prizes won at one of our local radio stations. Every morning one of the local pop/rock stations would do Movie Trivia. Caller #7 wins a prize type thing. I figured out the timing, which was pretty simple actually. At 7 AM, they'd play a promo sound, DJ reads the question, then play a song while they "go to the phones" and find a winner. But they didn't actually take the 7th call, they would just take whoever was on hold first. So I'd have their phone # queued up, wait for the promo sound, then hit dial. I won 3 days in a row before they recognized my name back to back. So then I started calling in and giving my buddies' names. Then my neighbors. Then my cousins'. Etc. Over the course of my junior year of high school I probably won 50+ prizes. CD's, movie tickets, concert tickets, restaurant gift cards, etc.