My husband used to use a portable DVD player often. Now he has his Kindle and uses that. He also has a few thumb drives with movies on them and they watch them on the computers.
Send him with a nice set of sheets, a cozy blanket and a couple of decent towels. There are not too many comforts of home over there, nice linens help make it more comfortable. Plus, he'll think of you when he snuggles into his bed. Also, send him with a few non-aerosol air fresheners. Even when it is cold over there, dudes are stinky.
When y'all are packing his things, use Space bags. Those things have helped make packing so much easier for my husband. We label every bag. He knows where everything is and it keeps him so much more organized. He has a ton more room in his personal space, as well.