Needless to say, this is a nickname for a very specific kind of dude, not specifically one who plays chess.
This is the kind of guy who always makes all the right plays, and receives an ungodly amount of rizz.
The "right plays" is originally based off the terminology used in the game, Chess.
Person 1: Hey! Did you see that sick guy at the party?
Person 2: How could I miss him?! He was a total Chessman!
Nickname given to bales of marijuana thrown overboard or out of airplanes. Origin is reportedly from members of the US Coast Guard in the area of Southern Florida.
A sunburn or suntan focused on the left arm. It is caused by the left side of the body being the only half that gets exposed to sunlight while driving. Presumably, it would be located on the right side of the body in countries where they drive on the left side of the road.
I had a trucker's tan after driving for 10 straight hours on a sunny day.