59 levels to play before you die: G - L

Gradius V (PS2) | Asteroids!
There's no shortage of shooter stages in this list, that's for sure. Makes sense, seeing as they usually only have five or so levels at all, so they've gotta make 'em count. Gradius V's asteroid-packed level is already hard, forcing you to weave your way through some ridiculously dense fields. Then, to top it all off, the boss makes you literally carve a path through hundreds of incoming obstacles while simultaneously avoiding all the crap it's shooting at you. Intense, insane, incredible.

GTA: San Andreas (PS2, Xbox, PC) | Breaking the Bank at Caligula's
Grand Theft Auto missions are famous, not only for their sheer, overwhelming quantity, but also for their incredible diversity. Games that are supposed to be about stealing cars have somehow expanded to include anything from pimping prostitutes to hijacking military fighter jets in midair.