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drbunnig said:
The original Tomb Raider perhaps? Read an article recently saying the sales target was 100,000 copies, and it ended up selling over 7 million copies and spawning a franchise that's still popular today.

Quite a few games of the time got pretty pessimistic outlooks in retrospect. Super Smash Bros, like I mentioned before, but also the original Warcraft and Command & Conquer games vastly outsold what their publisher had hoped (and kickstarted the RTS genre). Still, Tomb Raider is a good example due to how big that gap is

While we're at PC games, Wolfenstein 3D, Duke Nukem 3D and Doom could count, having started their lives as Shareware titles but having got full retail releases due to their immense successes (besides poplarizing the FPS genre and bringing it to the masses).