List games

Me and a friend want to play a coop game together but we can't figure out what to play. It needs to be early 2k or earlier and reasonable to play over hamachi or other such VPN's. We don't even care about the genre, we just don't have any ideas, please help and share experiences about fun coop experiences.

Serious Sam the first encounter and second encounter. Classic 2001/2002 version supports 4 player co-op, 2008 HD version supports up to 16

jesus christ spoiler that shit

Does it have to be coop, or can it be competitive?

That's not a bad idea, added to the list

Coop only, our friendship is not strong enough for anything competitive even though we have a very strong friendship.

Download MAME + MAMEHub and play some arcade games.

Cadillacs and Dinosaurs, Ninja Baseball Bat Man, Capcom's Aliens Vs. Predator, Konami's The Simpsons, TMNT IV Turtles in Time, the Bubble Bobble series, and the Metal Slug series are some personal recommendations.

I like the idea but I remember having some serious latency issues with MAME, am I remembering wrong or has the issue been addressed? It's been years since I used it.

C&C Generals
Diablo 2 (alternatively Diablo 2 with Median XL mod which is the true Diablo 3)
Doom 3 with OpenCoop
Half Life 2 with Synergy
Half Life with Sven Coop
Gears of War
Neverwinter Nights 1/2
Baldur's Gate 1/2
Icewind Dale 1/2
System Shock 2
Rainbow Six 3
Serious Sam 2 (not second encounter, 2 is the only non-shit SS game)

There's a bunch more, but that list should be good enough for now.

Also Sven co-op for HL1 (Sven itself doesn't require Half Life, it's free on steam) Synergy for HL2 (requires HL2)

you fokin wot m8 ? I like SS2, but SS TFE & SS TSE is the golden standard.