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NES era - Super Mario Bros. I don’t think anything came close, but if so, maybe Tecmo Super Bowl couch sessions with my brothers 

SNES era - Super Mario World or Donkey Kong Country 

PS1 era - Three games come to mind: Gran Turismo, THPS, and MGS. Probably GT

PS2 - easily SOCOM II. Closest second would be PSO on Dreamcast 

360 - CoD4 or World at War. Search and Destroy with work buddies

Xbone - Dead by Daylight. I think this gen was the gen of asymmetrical MP for me. Two of my favorite games were Dead by Daylight and Evolve.