I was going to answer "4th edition, and he leveled up," but then I remembered I tried playing once with a friend when I was a kid. I think it was 2nd edition, or possibly early 3rd. I made something called an 'earth elementalist', which I thought sounded cool, but could only cast stone fist and everburning log. After about an hour or so of wandering around the woods fighting 'gibberlings', I had to go home for dinner. The game continued without me, and I was later informed my character was eaten by a dragon.
I tried playing again later, with just him and me. I made a druid; he put me in an urban investigation adventure. So, yeah. Never really got into D&D until 4th edition, haha.