I think it becomes kinda iffy when you don't consider sales. I know my whole Steam library is worth 731$, but I haven't paid close to that much to get it. L4D2 for instance I got for free.
I'll use the values I paid for them:
Oblivion Game of the Year Deluxe - 15$
Witcher 2 Enhanced Edition - 5$
Crysis+Crysis Wars+Crysis Warhead+Crysis 2 Maximum edition (bundle) - 15$
Portal (was in a bundle with Portal 2 for 5 $, but I completed Portal 2, so let's say 2.5$ for Portal 1) - 2.5$
Spore + all extra content (sigh, why did I buy this?) - 15$
XCOM: Enemy Unknown - 10$
Skyrim - 15$
Risk of Rain - 5$
Dark Souls Prepare to Die edition - 6$
Castle Crashers - 1$
Race the Sun - 3$
In total 92.5$
I was surprised to see how much it actually was, thought I had wasted way less 
It was kinda funny to see that my first christmas sale was also the one where I wasted the most. That's when I bought Skyrim, TW2, Oblivion, Crysis, Spore, XCOM and Dark Souls, which amount to 81$ of the 92.5$. Since then I've basically only bought games I really wanted.