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

Definitely Doom, Heroes of M&M 1,2, and 3, Master of Magic, and Dark Messiah. Dark Messiah was like Doom in that it was very linear and easy to learn -- just jump right in and enjoy the action.

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