Two things:

I was working in Aspen in the winter of 2003 as the Iraq war was ramping up. One afternoon, locals had organized a "protest" in the town center and were wearing plastic "make snow, not war" ski bibs. I thought the anti-war message (that I believed in) was neutered by the ridiculous statement (and I was a malcontent punk rocker and, whatever). I went back to my hotel room and scrawled on a t-shirt, in giant black and red block letters with a marker, "MAKE METH NOT WAR." I had a fun time wearing it around the protest while people asked me about it. Then, to my surprise, it was announced that Hunter Thompson, a long-time Aspen resident, would be speaking. After he growled into the mic incoherently for 20 minutes, I fought through the crowd to find him. I had the black marker with me that I had used to make the shirt and I handed it to him. So, the first coolest thing I own is a shirt that says, in giant, hand-scrawled red and black letters, "MAKE METH NOT WAR" signed by Hunter Thompson.

A couple years before, I was drunk outside of a bar in NYC (probably around 2000). I noticed somebody making noise on the sidewalk and it was Ol' Dirty Bastard. He was with a couple homeboys and he was shouting about how he wanted to get some pussy. He kept yelling, "I'll fuck anything that moves." This was before cell phones with cameras so it wasn't drawing a ton of attention, just a few of us on the street being highly entertained by the site of Dirty being dirty. Eventually, I started digging around in my pockets for something for him to sign and I discovered my social security card and realized that I had never signed it. I haven't seen it in years but, somewhere, buried in a desk drawer, I have my social security card, signed by Ol' Dirty Bastard.