I had the same problem - especially as it holds so many !!
Me and a friend (after a few drinks) started (with a bit of paper and a pen) thinking of our earliest memories (of being a kid) through school then first job, first everything else!! and all that.
It's amazing the ones you forget !!
You can try them out (for 30 seconds) no charge in the i pod store
My fav's
David Bowie - Life on Mars
Paul Weller - long hot summer & Living on a wire
Nirvana - Smells like teen spirit
Joan Armatrading - Love and Affection
Vicky,
There's a very good little book you should be able to get in Waterstones/ Ottakers etc. called �The Rough Guide Book Of Playlists� (Rough Guide 2005). It divides music into genres & headings, and recommends 10 or so songs under each. Of course, it's only someone else's opinion, but is quite interesting anyhow. Hope this helps!