Launch PS2 as a Christmas Present and the incredibly awesome Fight Club DVD set. Perhaps that was a mistake, as I henceforth expected all DVD sets to be that comprehensive. Whoops.
I bought an Emerson DVD player and my first DVD/s was an Action 4 Pack that included: Dumb and Dumber, The Long Kiss Goodnight, Spawn and Mortal Kombat Annihilation.
Yeah, my first movie was Princess Mononoke as well, I got that before I got a DVD player ... first DVD player was PS2, Xmas 2001. Though my brother had one on his computer earlier.
I got my first one in 1997, and it was $750. No really, it was very top-of-the-line for it's time. My first DVD...well, I bought about 8 movies so there were a few, though I'd have to say Austin Powers is what impressed me the most at the time.
I remember a web site called DVDresource, and it was great, almost better than thedigitalbits. Too bad the guy was hated out of the site. Another good site is dvdfile.com, but they're getting as bad as digitialbits now.
first was a pioneer dv505 around 1995 - awesome first player, and I self modded it to be region selectable. Actually bought it in Japan for cheap because no one was buying them at the time. Cost me about £150, which was really cheap back then.
First DVD I think was LA Confidential, or possibly Terminator 2 from Japan.
Now have a philips 963SA, which i upgraded to for PAL progressive scan. And its lovely.
I bought a ProScan DVD player in 1998 ($400! It's amazing how cheap they are, now!).
I don't remember what the first DVD was that I bought, though. I think it was either The Killer or Hard Boiled (both Criterion).
I just bought a Zenith DVB318 DVD player. Upconverts to 1080i via DVI or component, plays all region and converts PAL to NTSC. Love it. And it cost about a third of my first player.
First half of 2000, I don't remember exactly which month, but I think it was April or May. A Sony 550, for $450. First DVD I bought was the Army Of Darkness Limited Edition, from some guy on eBay. Before I even had a player. In fact, I bought a DVD player mostly because of that DVD set. First DVD I bought in a store was Suicide Kings at Wal*Mart for 7 bucks. When everything else was 20+, that seemed like a great deal.