I think my favorite would have to be my first walkman, less because of the walkman but the circumstances behind it. My parents had just gotten divorced (I was 15 at the time) and things were really ugly, between the lawyers and the overall bitter vibe that was going around Christmas was barely spoken about. I had chosen to live with my dad and he was really struggling.
One night he asked me what I wanted for Christmas and I told him not to worry about it, finally he pryed it out of me and told me he couldn't make any promises. So sure enough Christmas morning it was there, but I realized the sacrifice it must have taken for him to get that for me. That Walkman lasted me ten years I took such good care of it and I cried when it died