I have a few signed LP and cds but most of what I have signed are my photographs of them. Without fail, if I see a musician that I have photographed before, I always give them a matted print. This generally jumpstarts a conversation on when/where it was taken, who they were playing with, why they are wearing what they are wearing, their hair style and so forth. I saw Russell Malone, John Clayton and Monty Alexander do a tribute to Ray Brown shortly after Ray died. I have some nice images of Ray from one of his final shows and gave each one of them a print. Each one of them also signed one print for me. I've seen Russell Malone a few times since then and the first words out of his mouth is usually, "Hey, where's my picture"!!!
Anyway, I have no qualms about asking for an autograph if the times right!
m~