Dont go for an iPod, overpriced and overrated.
I did some research, tried out a few MP3s in shops and finally broke the mould and went for this:
ttp://www.amazon.co.uk/Sony-NWZA818-Video-Walkman-Battery/dp/B000VD2130/ref=sr_1_1?ie=UTF8&s=electronics&qid=1210377299&sr=8-1
Its a Sony Walkman MP4 player.
Fantastic little gadget:
-Very small, very light and very thin (weighs as much as a nano) and easily gets lost in your pocket

-BRILLIANT sound quality (the default headphones are worth £40 alone)
-Great colour screen for watching videos.
-Brilliant value for money.
-No need for software! you can do a simple 'drag and drop' to transfer your music, pictures and videos. If you like your playlists then just use Windows media player and sort out our library as you would with iTunes.
-35 hours of battery life....you barely need to charge the thing.
I would seriously recommend it, picked mine up a few months ago and I havent looked back since. You've got to see and try the thing out in person to really appreciate it though.
p.s: The model ive shown you is an 8gb model, of course there are 2gb, 4gb and 16gb (with bluetooth headphones

) variants.