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[KO Traveling Hobo]

Dorf Fort, I Wanna Be the Guy(except against bosses), Left 4 Dead, and Spelunky co-op can all be a ton of fun to lose.

I'd much rather watch other people lose, though.

 

[reggie]

.

 

[Alaskanbullworm]

TF2 - doesn't matter if you ever win, especially if you frequent an active community
Smash Bros - always an amazing experience, but only when it's not with one of those people that like using the exploits
Bubble Bobble - Definitely helps how easy it is to continue, it's so easy to die and so fun to mess around in
Mario Kart - everyone yelling at the comp is amazing
Goldeneye - first game I can remember everyone getting together to play and everyone would have fun no matter the outcome
Halo PC - Very similar to TF2 level of fun, although that time has passed so many years ago

Edit: Ohhhhh I have to add on Banjo Kazooie Nuts and Bolts as well. Amazingly fun, EXCEPT when your save file keeps on deleting itself. I'll never be able to 100% that game because of that

 

[Sentenza]

This. TF2 is always fun.

Dota 2 is the most bipolar gaming experience of my life.

Yep, it can range from "galvanizing and empowering" to "extremely depressing" in less than a hour.

 

[Grayman]

Fate of the World is goddamn hilarious when you're losing. it might actually be more fun that way.

some of the scenarios and achievements encourage this

 

[ViewtifulJC]

Team Fortress 2 is the first one that comes to mind. I have a few favorite servers I visit with a lot of regulars who are quite good at the game, and every time I boot it up it feels like visiting old friends. You obviously play to win, but even when you get steamrolled it can be fun(plus, TEAMS ARE BEING SCRAMBLED helps evens it out a bit). I've put hundreds of hours into that game and it continues to amuse me, beyond just the fancy hats.

 

[The Hermit]

Mario Kart, but only when you are playing against other people, not computers.

This. Local play I mean, when we can laugh at each other.

 

[Alo81]

The treasure chest levels in Rayman Origins are amazingly fun, even when you're losing. I'd even say especially when you're losing, because I was disappointed with how easily I was beating the late game treasure chest levels.