If he doesn’t have one already, a portable MP3 player is a great way to bring your dad into the noughties. They can be bought quite cheaply now, and you can readily get 4GB capacity devices for under $100. Apacer, in particular, makes cheap, high capacity devices – but they’re also deeply ugly.
We recommend Creative’s Zen Stone Plus because it strikes the right balance of capacity, features and price, without looking like it came out of a 70s industrial design shop. In addition to having 2GB of storage capacity, the Zen Stone Plus has a radio tuner, voice recorder and stopwatch. It serves as a portable flash drive, has a decent battery life and doesn’t require him to install any software on his PC. Later, you can buy him the armband and keychain extras for carrying it around. (Really, one of the great things about portable MP3 players is that they create a handy ecology for future gifts, so you won’t have to think too hard about them.)
Of course, the downside to giving him a portable MP3 player is that the gift often has to come with a lesson on ripping CD collections and downloading new tracks. Depending on his technical nous, this can take minutes or hours.