Off the top of my head.
All DLC in: Halo 3(three times), Halo Reach, Halo 4, Gears of War 2, Gears of War 3, Fallout 3(two times), Fallout New Vegas(three times), Skyrim(two times), Killer Instinct Season 1, Binding of Isaac, Binding of Isaac: Rebirth, Lisa, 100% Orange Juice, and ALL Call of Duties from Modern Warfare 1 to Black ops 2.
I've also spent at least $400 on items and keys in Team Fortress 2, and CS:GO.
This is but a fraction of what I have bought over the years DLC wise. I have no regrets on these purchases and I know I'm the problem.