Can a wire gauge be too large?

Extension cords are prime examples of "do your homework" I have a Craftsman air compressor that has a 4 foot power plug, useless. So I haul out my 50 foot green cheepo extension cord and fire it up, well it sounded like a Volkswagon starting with a dead battery..wump-wump-wump-fzzzzz! Blew a 20A circuit breaker in my panel, garage went dark. Then I tried the heavier orange one I have. That worked decent but the compressor never did build pressure and the wire got physically hot. Nix on the extension cords!Maybe I should have read the manual? I then bought 20 feet of stiff 12/2 Romex and wired up a plug on one end and a plastic J-box on the other and installed a receptacle. Now that baby kicks over like it was plugged straight into the wall.