I just checked in my allknowing excel file, which were the most expensive games I ever bought... there weren't very many for more than €50:

And most of them included some valuable physical extras (PSVR AIM-controller, a €40 PS3-headset, a solid Big Daddy statue, a huge ME:C box with an awesome Faith-statue, a pretty steelbook or a guitar controller:






Others were more expensive because of import costs of uncut versions (the German versions of Hellgate: London, Resident Evil 4 and CoD: Modern Warfare were cut)... and yeah: buying Hellgate: London wasn't my best decision.
My most expensive digital version ever is Half-Life: Alyx, followed by "The Orange Box" (including HL2, Portal + TF2).
Any other digital version I ever bought was under €30:

I also found my oldest receipt of a video game: in June 1992 I bought Monkey Island 2 for 70 DM (~36 Euros), my first pre-order game ever. It was "day one" for the Amiga version, the PC version was released half a year earlier:

A few years ago, Ron Gilbert signed my MI2-box, and the code-wheels of MI1 + MI2:










