Dont remember that much back but...
2013 - GTA V (Xbox 360)

PS4:
2014 - Watch Dogs, The Last of Us Remastered, The Evil Within, COD AW, Dragon Age Inquisition, Wolfenstein TNO
2015 - Bloodborne, Witcher 3, MGS V, Batman AK
2016 - Doom, COD BO 3

These are the most expensive 50$-75$

I bought Lunar Magic School for Sega Saturn, the collectors edition with cards import for $250. That's the most expensive game I ever bought.

I only remember this year and the most I've paid is $60

Well, technically, add on items aren't games so, whatever you spent on the GAME, is what you spent. 

I think the most expensive game I ever bought was something like, 70 dollars back in the day on an SNES game. Carts were expensive.

This is kinda hard to track it all down, i think i had even a year were i wasnt even into videogames anymore and didnt bougth anything. If we also count older games the most i have paid this year was 240€ for Real Bout Fatal Fury 2 the Newcomers on the Neo Geo which was a good deal. I paid 110€ for Atelier Sophie PS4 CE if we talk about new/relevant systems for this year.

Don't remember previous years, but in 2015 it was Black Ops 3 Steelbook Edition + Season Pass for 120€.

The most I've ever spent on a single game was Splatoon when it came out. I paid R$250 or $78 for it. Besides that, I mostly get games for cheap (Especially during Steam sales).

Amazon gives 20% off new games for prime members. They are also giving me 20% off the figures and technically they are not a game but the discount still applies like the characters are a new game. Regardless, you need the characters to play the game, so the game IS the characters. Are you as confused as I am now? Good.