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I rented Superman 64 three times from my Blockbuster, The multiplayer on that game is actually salvageable
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Ghorpm: Dungeon Keeper 2

Bugs, crashes, glitches... I think it's not neccessary to continue - if you've played it you should know what I mean. But the game is excelent nevertheless!
Agree with this one - second in the Bullfrog catalogue only to Theme Hospital IMO, but it has some pretty bad bug issues
Boiling Point aka Xenus

Tons of glitches and a few poor design decisions but it's still the kind of open-world game that I enjoy. Haven't gotten far enough in Precursors or Xenus II to call either of them my favorite broken game yet.
Vampire The Masquerade: Bloodlines

The unofficial patches have fixed a lot, but at release the game was fairly bad for bugs and glitches.
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mondo84: One game I had a little trouble with was STALKER on Vista, but patches fixed the various bugs. It's a great game.
Only a little trouble :)

Personally I find the game unplayable without at least the zone reclamation project installed; the hit detection being the main issue for me. Granted, I guess the game was designed that way intentionally?! Looking past the problems, it's one of my all time favourites!

Space Marine is also a favourite of mine, but the autosave has stopped working since steam updated it to a 'more efficient file system' or some such :(
Bloodlines, Arcanum and a ton of other RPGs. I never had a problem with Alpha Protocol personally but a lot of people did.

On the shooter front I can't really think of any.
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TheJoe: The Guild.

It's broken everywhere and it looks horrible BUT IT IS THE BEST GAME EVER MADE
Love it too. Never regretted the Purchase.
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StingingVelvet: Bloodlines, Arcanum and a ton of other RPGs. I never had a problem with Alpha Protocol personally but a lot of people did.

On the shooter front I can't really think of any.
Arcanum???

Darn, I played that one a good 40-60 hours (didn't finish) and didn't notice any bugs that I remember. Was your playthrough right at release perhaps??? (mine wasn't, it was much later, as always with me).
Mine was a game on the PS2 called Dark Cloud. You had to fight through dungeons and collect pieces of towns that had been trapped by an evil magic. You would collect everything from buildings and villagers down to trees, fence, and roads. Then you would rebuild the village however you wanted. It was challenging, and each dungeon was randomly generated through each playthrough, making the replayability quite high. The only problem was when I reached the second to last dungeon and the game randomly generated the last key on the wrong side of the last door.

Game over.
Well with just gameplay bugs, Skyrim and Crysis.

Both games had no end of bugs for me, but they were usually hilarious. I very rarely physically laugh out loud at something which happens in a game but Crysis in particular had me in tears with some of the random stuff that happened.

Considering other problems, crashing etc. Probably Fallout 3. I know a lot of people around here hate it but I really enjoyed the game, enough to put up with it through all the crashing/gameplay breaking bugs at least.
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Goatbrush: Well with just gameplay bugs, Skyrim and Crysis.

Both games had no end of bugs for me, but they were usually hilarious. I very rarely physically laugh out loud at something which happens in a game but Crysis in particular had me in tears with some of the random stuff that happened.

Considering other problems, crashing etc. Probably Fallout 3. I know a lot of people around here hate it but I really enjoyed the game, enough to put up with it through all the crashing/gameplay breaking bugs at least.
Really? never played the game, but I always see that game and fixed outside the box.
King Quest VII. Can't count the issues like, no more pointer control closing to desktop and crackling sound yet i loved playing it along with my little niece.
Oblivion. The retarded level scaling makes it a broken game.
But heavily modded I enjoyed it.
Not my favorite game overall, but probably my favorite 'broken' game: Neverwinter Nights 2. The game went through a ton of patches and I know a whole crapton of people had some serious issues with it when it was first released. I was lucky enough not to encounter any game-breaking bugs when I played on release, but there were a truckload of other bugs (major and minor). Many were eventually patched out. But yeah, that's probably the one I'd say is my favorite broken game.

Alpha Protocol is another game that's widely considered a bugfest (I personally don't understand why). I really really enjoyed it, but as with SV, I didn't have any bug issues with it when I played it. But I picked it up long after release.
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Elmofongo: Really? never played the game, but I always see that game and fixed outside the box.
Oh yes it's full of random bugs. There's some gold on youtube if you search for them there.

http://www.youtube.com/watch?v=vDkD1Vj5o64 compilation of a few.