As far as player goes likely something from Fisher-Price or another toy manufacturer would dbe the most durable...

I know FP made a cassette player a few years ago, that a young 2nd cousin of mine had, and it was damn near indestructible...

Except that a CD player needs a fairly well focused laser to do the reading... even small bumps can mess them up...

How about a minidisc player? They are *in his best Tick voice* "nigh-invulnerable"

and well, headphones eh? -I- even manage to go through ear buds, and standard 'walkman' type headphones like there's no tomorrow... They all pretty much suck... I think that's the plan so we have to keep buying more...