On the day he was born: Resident Evil 2

Within his own universe, Leon was born in 1977, making him only 21 when he debuted in the 1998 PlayStation game Resident Evil 2. But to us, Leon was born on his fateful first day as a cop.
Early concept art positions Leon as spry boybander, with a slim, Peter Pan face and a fitted Raccoon City police uniform, though, in-game, he looked a bit more like a puffy, stuffed scarecrow than a Justin Timberlake stand-in. 1998 graphics could only handle low level boyishness.