King Nerd with an original Late Night with David Letterman shirt in the mid-late 80's.
David Letterman was truly the late night voice of my generation during his NBC run from 1982-1993. Having watched The Tonight Show with Johnny Carson as a very young child, I was familiar with the talk variety format. When Letterman debuted, he was the anti-Carson and he quickly separated himself from the status quo with bizarre bits and the 4-piece house band.
My friends and I watched Late Night religiously and dissected the shows the next day. Viewer Mail, Stupid Pet Tricks, Wacky Suits, great guests (Andy Kaufman, Teri Garr, etc.), Chris Elliott's Guy Under the Seats, contemporary musical guests... and he made it ok to wear sneakers when dressing up.
Coincidentally, we both moved in 1993, him to CBS and me to Nashville. I stopped following the show soon after but would pop in occasionally. Conan O' Brien has been the most successful at capturing the spirit of the Dave's NBC tenure but... Dave was the first and he was our king.