As far the most fun I had with friends, they're all on N64.
1. NFL Blitz 2000
2. Wrestlemania 2000
3. MLB Featuring Ken Griffey Jr
4. WCW Revenge
5. NBA Showtime
Wrestling is sports entertainment, but it's still a sport so I added to my list.
If wrestling games are in then any of the wrestling games made by THQ for the N64. My favorite was No Mercy tho, been recently trying to get mods working for it.
For football/soccer games it would have to be sensible soccer or international super star soccer.
What was your favorite. Used to like King Slender, but later on, it was Star Man FTW. Did you know there's a real wrestler using the gimmick? Must be at independent shows or else he's probably get sued by Nintendo haha:
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