Right now Sony seems to be phasing out the original PSPs, and IS literally forcing people to rebuy every game over their site when they get a PSP GO if they're switching from UMD to the new PSP for whatever reason. Basically this means that games will be placed on a memory stick, and UMD is being made obsolete.
I personally would probably still get an older version, the generation 3000. It will be cheaper, and I have a feeling that since Sony seems to be giving up on UMDs, that there may be a major blow out down the road and you may get some decent deals on games and maybe movies.
So a bundle
1 : PSP 3000; this should come with headphones, a battery charger, and several other accessories.
2 : Check the box before you buy this as the PSP may come with one, but a decent memory card, memory stick pro duo type (at least that's what mine uses).
3 : A game or two! Maybe he'd like Gran Turismo? It's a decent driving game from the reviews I've seen. There is another game called Rock Band Unplugged that he may like. It really depends on him.
4 : A plastic screen cover, to protect the screen from scratches. (Trust me, this is more important than it seems)
Take care!