Adding some additional clues.
#50 Main guy is named Trent, that will probably narrow it down. If not, eat some hot dogs or bananas while I try to come up with another clue.
This space shooter came with its first episode as shareware in the mid nineties and today the whole game is freeware.
#49 Released after one of the most popular racing series first title but on a system one generation behind. This third installment also featured weapons to make life miserable for the other racers.
In the races you could collect letters spelling the game title in order to upgrade your vehicle. The developers next racer featured a mammal with a red cap as its titular character.
#46 Developed under difficult conditions this lucky accident of a game topped the bottom of its time.
Maybe not really the bottom of its time, but last place of the big three. Some of its glitches are today more viewed as features by those who still play the game.
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