Where do I begin?

No, but, really—where do I begin? The original show hadn't been off the air long when I was a kid so that's where I started. The Next Generation went on the air when I was a teenager. But I'm not sure where to start with a savvy youth of today.

Does it makes sense to present him with the originals or will they seem to hokey? Should I try with one of the later series? I've never actually seen Enterprise or Voyager (though I quite like Mulgrew.) Should I avoid starting with the shows altogether and try movies first?

What would you do?