My first anime was Cardcaptors or Pokemon but at that time they were just some cartoons on TV. The first anime that I watched knowing what anime was, was probably Shuffle. Can't remember why I picked that one to watch but its been all downhill since.
I watched Naruto a long time ago, but didn't start seriously watching anime until Angel Beats!. Though I acknowledge now that it wasn't very good, I thought it was great when I first saw it.
Pokemon and Dragon ball, many many years ago. Then I didn't watch anime for about a decade and a half and one day just decided that I need to start watching it again.