Since you mention Hofstadter, I simply have to bring up Godel, Escher, Bach. Especially for anyone who's interested in computers and artificial intelligence, this is a must read. It is brimming over with philosophical issues, and is very accessible even to someone without any previous exposure to philosophy.
I'd also recommend "The Cyberiad" by Stanislaw Lem. It's an anthology of hilarious science fiction stories, many of which deal with deep philosophical themes. Also, along those lines is Douglas Adams' Hitchhiker's Guide to the Galaxy trilogy, which is also hilarious and very philosophical.
These aren't exactly the first books most people think of when asked for intro to philosophy books, but I think books like these are quite perfect as very easy, gentle, funny and fun intros to many philosophical themes. Their humor and wit also put the vast majority of "real" philosophy books to shame.
A colleague of mine with a background in semiotics recently read Godel, Escher, Bach, and said it was, among other things, to his surprise a good introduction to something very similar to semiotics, but independently derived by Hofstadter from first principles.
I'd also recommend "The Cyberiad" by Stanislaw Lem. It's an anthology of hilarious science fiction stories, many of which deal with deep philosophical themes. Also, along those lines is Douglas Adams' Hitchhiker's Guide to the Galaxy trilogy, which is also hilarious and very philosophical.
These aren't exactly the first books most people think of when asked for intro to philosophy books, but I think books like these are quite perfect as very easy, gentle, funny and fun intros to many philosophical themes. Their humor and wit also put the vast majority of "real" philosophy books to shame.