42. His Knowledge Is Encyclopedic
Announcer: Dean Windass
Becoming a commentator or analyst has been the go-to move for athletes looking to continue caking up toward the latter part of their career and into retirement. The switch isn't always seamless, though. Footballer Dean Windass has a bit of trouble on the mic and basically just says "fuck it" when trying to recall a player's previous club. Pretty bad, but would you care about your commentary if you had Windass for a last name? Us neither.