Ok, here's the list of what you need to do to win this achievement (Tested myself, this is what unlocked it). You need to complete everything on this list. Either by winning, or getting the highest score where applicable. You MUST finish, you cannot DNF any of these or they won't count as completed, obviously.
- Land Race (2 players)
- Air Race (2 players)
- Sea Race (2 players)
- GTA Race (2 players)
- Rally Race (4 players)
- Deathmatch (2 players)
- Team Deathmatch (4 players)
- Complete all 10 Waves of Survival (Solo, but 2 players at least... Use the Sandy Shores method)
- Gang Attack (Solo)
- Golf (1 Hole, 2 players)
- Tennis (1 Set, 2 players)
- Darts (2 players)
- Arm Wrestling (2 players)
- Parachuting (2 players)
- Any Shooting Range Challenge (2 players)
EDIT: Despite contrary belief, Vehicle Deathmatch is NOT a requirement of this achievement. I and several others who boosted this unlocked the achievement without ever playing a single match of VDM.
- For Rally Race, 1 lap Criminal Record and just invite everyone, you're guaranteed to get a bunch of suckers who don't know any better and most of them will try to "GTA Race" each other, if you get what I mean, when the match starts. So you'll easily get this win there.
- For TDM, similar deal, set it up as 10 kills over 5 minutes, turn team balance off and watch how fast one side stacks against everyone else.
- Parachuting, you MUST finish, landing off target gets you a DNF as if you hadn't done the mission at all.
- For 10 waves of survival, see the
guide for best locations. I did this with one other guy on Sandy Shores using the trash bin location for shooting. My co op buddy did nothing but die spectacularly, so that's the only reason I don't say I did it solo.