Spyro the Dragon: Ripto's Rage
Whenever my brother, sister, or I played the level Sunny Beach, the three of us would bet on which baby turtle would make it to the very end of the level (by the portal back to Summer Forest) first.
Since there were 3 of us and 3 turtles, it worked out pretty well lol.
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Also the first time I played Simpsons: Hit & Run, I crashed my car into a streetlight in front of the Kwik E Mart cause I had to go inside as part of my mission. My dad and I thought that was pretty funny