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Probably never, both have been rebooted and the Halloween people said a few years ago they don't want to do a crossover.
Lori Singer
The movie specifically made after Jason X that stared Jason Voorhees was 'Freddy Vs. Jason'.
They are both tough guys, but Jason is an immortal zombie and Michael Myers is just a tough guy Michaels that can't die so probably a tie. I think Jason would win mostly because he has a longer weapon and has killed more people. Any true horror fan knows that Myers would beat Voorhees's behind without any effort. think plain and simple, Hell already has Jason, while Myers is too powerful for hell, watch Halloween 5 it states that Myers evilness is too much for even Hell. Also, weapons don't matter. Myers can grab a machete and start killing with it but he don't need it because unlike Jason, Myers can look good with a small knife.
Michelle Pfieffer was the main star and her costar was Wade Dominguez. They made a terrific movie that is still watched to this day in some local theaters.