It’s been so long that I can’t remember the first DVD but the first Blu-Ray is more recent. That was definitely the Coppola restoration of the Godfather trilogy.
Blazing Saddles.
Pi
I don’t remember the first one I bought for myself but the first one I saw was copy of Star Trek Generations my friend got free when he bought his. The picture quality impressed me so, I literally went out the next day and bought one of my own.
I bought a player along with Fight Club, The Matrix, and the Southpark movie all in one day.
The day I got a Blu-Ray player, I bought The Dark Knight.
I’m not sure which I actually purchased. My wife and I got a DVD player for ourselves on Christmas Eve, and my wife bought me The Exorcist. We still watch this almost every Christmas. Yes, it’s a weird family. 
Black Book. I got my first DVD player in 2004, but I was content with renting until then. I don’t really rewatch many movies; I buy more as my way of hopefully ensuring more movies like the ones I buy get made.
I stopped by some large box appliance store like 10-15 years ago and they had some off brand DVD players for like $12.00 (Apex or something). I figured at that price, why not? They didn’t have too many DVDs so I wound up buying Jumanji, which was actually pretty cool as a first DVD.
On a side note, the $12.00 DVD player still works just fine.
The Dark Knight was my first Blu-Ray purchase as well.
The first DVD I ever owned was a campaign DVD from the John Kerry campaign! The first DVD I bought was a Genesis concert from 1987 at Wembley. I didn’t buy DVDs for a long time since I had the library and Netflix.
Same here!
I didn’t remember, so I looked back at my Amazon account, and there it is, in 2002.
Monsters Inc.
I bought mine before I had a TV or DVD player, to use with my PC.
Men in Black, the special/collector’s edition.
Wow. Has it really been that long?!?
American Beauty. I love that movie.
First DVDs I ever bought were the box set of ‘Sportsnight’
The first singular DVD I bought was ‘The Princess Bride’, the 25th anniversary edition.
Both purchases I can look back at through the years and smile.
Definitely. It had this thing called “special features” that showed how they did the bullet time stuff.
It was pretty cool at the time.
The first one I bought was Clerks.
Me too! I love that movie.