The final chapters of Asura's Wrath and I don't regret it at all. An incredible ride all along, wish there was an edition with everything included so I can recommend it to my friends easily. This game would benefit a lot from a port to this generation.
It was the Jetstream DLC for Metal Gear Rising: Revengeance which offered a fresh take on the already great combat. A few new locations would have been cool, but hey, taunting is super fun!
If we're not including DLC attached to "GOTY Edition" or anything, probably TLOU: Left Behind. I bought it because TLOU was an amazing experience, and I wanted more story and gameplay from that experience.
Mine was the Eagle Watch expansion for the original pc version of Rainbow 6 in 99. For Xbox it was the Halo 2 multiplayer map pack since anything I had downloaded on Dreamcast was just the free dlc stuff.
It was Oblivion on the X360, but not the horse armor.
The Orrery was the first DLC I ever purchased for any game and man, did I enjoy it. I was already a part of the Mage's Guild and running a mage build, so buying the DLC was a no brainier for me.
Fast forward 11 years and I wish I could give back some of the DLC I've bought.
Bring Down The Sky for the first Mass Effect. The DLC for the Mass Effect Trilogy, all of the Souls games and Skyrim are the only DLC I've ever purchased (none of the cosmetic/convenience stuff, but the full blown mini expansions). Bought Shivering Isles too, but it was a legitimate expansion, not just DLC.
Before PS4, I always played offline. I associated DLC with multiplayer competitive games like COD, not my favorite genre. Then came Bloodborne on PS4 and I wanted to experience the game with its online components. Buying the DLC was a no brainer, and saying that I was not disappointed would be an understatement.
BFBC2 Vietnam and it was worth it.
Before that I never felt the need to buy any DLCs. I didn't spend much on games back then as well since money was tight.
I agree, horse armor or some maps aren't really on the same level. And, you can correct me if I'm wrong, but i believe Lord of Destruction and Brood War (which I also saw) weren't downloadable at the time they launched.
The very first car pack for Project Gotham Racing 2. Love that game. Prior to Halo 2 coming out I spent many an evening on XBL with it and Rainbow Six 3 Black Arrow.