Well, one that maybe went full circle for me is "bring the pain" by mindless self indulgence. At first, it just seemed like a really fun song that I loved. Then one day, a black dude was in my car listening with me, and he was like "wtf is this song about?". That's when it hit me that the song actually sounds REALLY racist. I looked up the lyrics and that just confirmed it for me. And then years later, I found out it was actually a cover of a method man song, and not really racist at all, I guess. But thats a weird one, maybe best not for white guys to be singing it...
I saw MSI sometime in the mid to late 2000s. It was at a club in DC and Jimmy Urine said, sorry I can't stay after the show and make-out with anyone because I got mono for some teenagers I made out with a few days ago.
It was very odd to announce in the middle of the set. I knew he was a year or so older than me and I found it very disgusting that he was talking about making out with teens so nonchalantly. Jimmy was probably about 30 at the time as I was late 20s.