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When I was 5 my parents bought me a Sega Master System and a ton of games as a birthday present, the rest is history...

Castlevania SOTN: What is a man!? A miserable pile of of secrets.... becasue its hilarious and kind of true

anything from Odd World Strangers Wrath: "whats the password" "ugh...squirrels ass?"...

Yup Ninja Gaiden on Xbox, the controller didnt really break but after slamming it down but it always squeaked when I held it.

Probably Castlevania Symphony of the Night, played through it countless times, I memorized the whole map and the order you explore the castle in, also bought the Japanese Saturn version to play as...

Can't remember but it was during the DC/PS2/GC/XB era because thats when I started to have my own money.

I buy physical copies, I'm a collector but also just old school like that.