If you can't count, 5 is countless.

Remember the Terry Pratchett novel Soul Music in which a rock band has a troll as a drummer. Trolls can't count higher than two, so when he counted off the beginning of a song, he would say, "One, Two, Many, Lots!"

I think I've played every chapter of Bayonetta on at least the three major difficulties on three consoles with two characters on at least two of them. So thats a minimum of 15 times from start to finish. But there's probably at least another 5 on top of that and most chapters many many more times for grinds, secrets, score and just because.

You've really done all 4 levels of the campaign 5 times? I'm still working on my 1st one and it's been years. Each stage takes sooooooooooo many hours with the dwarves horribly scatterbrained "ADHD" AI.
I do know, but I also took different upgrade paths the different times (Except anti-missile. That one's always necessary.), etc. Deus Ex is a good game to replay.

Definitely System Shock 1 & EYE Divine Cybermancy for me.

Fable
Lord of the Rings: The Battle for Middle-Earth
Mass Effect
Star Wars Knights of the Old Republic
Star Wars Knights of the Old Republic II

When the Gods shared humour with humankind you definitely weren't around, were you? :-D

That reminds me -- Why isn't Dark Messiah on GOG? I don't think the disc version had even any copy protection.

https://www.gog.com/wishlist/games/dark_messiah_of_might_and_magic_1

Aside from things like Minesweeper and solitaire, I can think of only a small number off the top of my head:
- Spelunky (44 wins and counting)
- Discovery: In the Steps of Columbus
- Rebuild (original Flash game)
and, somewhat embarrassingly,
- HunieCam Studio How do you beat a sandbox game with no story, no "final boss", etc.? I don't think the original, unmodded M&B has any explicit win condition, does it? (And no, retiring from adventuring doesn't count, as you can do that whenever you want. ;) )
If we're going that route, I could say I beat Banished, just because I decided I was done with a particular town. :P

[i]-We rocks throws - yous goes no farmore. Witcherses understanded?
-We understanded. But we still gotta get to the Circle of Elements.
-Listen, Butwe. Trolls come no to witchersy castle.
-Rocks lots there. Pretty rock.[/i]

Age of decadence...because it's so very replayable with all those different quest lines, and I wanted to see as many endings as possible. Probably played through it at least 20 times.
Not sure about anything else, I might well have played through the Baldur's Gate games more than five times when I was younger (eventually I got so over-familiar with BG2 I can probably never play that again).

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I rarely replay many games; I like to have new experiences but games I've replayed over 5 times...

Fire Emblem Blazing Sword and Starcraft 2:Wings of Liberty come to mind.

There's other games I've replayed a few times but not 5 times.

I rarely replay games, and if i do it's usually under 5 times.

That being said, i've beaten Resident Evil 4 probably at least 15 times...

'm going to 2nt Fable, Mass Effect and both KOTOR.

I'm going to add Morrwind, Skyrim, Knight of Xentar, Ninja gaiden (nes), Golden eye