Used/out of print: Realms of Chaos: Lost and the Damned (it was like $110 at the time, so I guess that was a good investment). Still probably the prettiest game thing I own. Adrian Smith pencils, geez.
I used to live in Australia, so paying a premium on games was just a given. I remember I bought some collectors editions of some 360 games and that bumped up to $150AUS.
I bought Titanfall and the season pass at release. I think it was $85 or so. No regrets. I got a lot of enjoyment out of the game and the season pass allowed me to look forward to the DLC packs rather than stress about their coming arrivals.
I bought the special edition of Fire Emblem Fates last year which was like, $70, which is the most I’ve paid for any one game like that. I did get the FE: Awakening 3DS in 2013 which was $230 but I literally didn’t have a 3DS before that so that was like, a console purchase too.
I don’t know the exact number but I definitely spent close to $200 on Dota 2 items. that was spread out over ~2 years so it didn’t like, ruin my life, but boy those $3 sets and $10 compendiums add up over time huh.
Skies of Arcadia: Legends on Gamecube. Paid $80 for it at a local used games shop, and I still haven’t played it. It’s been on my bucket list for years.
Games like DotA (ie, ftp) present an interesting issue. I often spend a little money in them every so often because I feel like that’s the right thing to do. But I’m also the weirdo that goes back to pwyw games and “buys” more if I think I would up underpaying the first time.
I mostly said WoW because I tend to never buy anything more than the basic edition of anything and often buy second hand but wanted to include some sort of video game. I imagine it’s going to be MMOs for most people if we talk lifetime.
Base game, five expansions, subscription fees for about seven years, buying 25K gold so I could power level jewelcrafting at the start of Burning Crusade.
When eBay and I were both young and spry in the late 90s I would pay top dollar for terrible Japanese N64 games. I forked over $100+shipping for an Evangelion game with frustrating controls and then again for the interesting but flawed Wonder Project J2. I really wanted to like both! I understand that $100 for a game isn’t all that much but to a baby highschooler it was probably the most I had ever spent on anything and felt like a fortune.
Not including my constant subs to FFXIV and the money I keep giving Blizzard even though they do nothing to deserve it… I once paid a little over $100 for the collector’s edition of Dishonored 2. I loved the first game and the second I saw the goodies that came with it, I pre-ordered it during E3.
(I know you’re not supposed to, but sometimes I take off my glasses and grit my teeth and wear the mask for a few seconds.)