Cheddar Bob is known as Jimmy’s (Eminem's) dumb friend in the movie 8 Mile, who is slightlyretarded and ends up shooting himself in the crotch.
1) Busta: "Cheddar Bob ass nigga shot himself in front of Def Jam."
2) John: "I wouldn't put that gun in my pocket if I were you. You don't want to pull a Cheddar Bob"
When Jason returned home from working out his wife threw him on the bed and said let me lick your ball sack. He immediately said alright you Cheddar Bob.
Someone who enjoys wearing flatbills and graphic tees on the weekends. Commonly referred to as a GDI. Known for being impolite and socially awkward, and starting fights with other random cheddar bobs.
Jim: What are all these kids doing wearing flat bills at graphic tees at a party?
John: Yeah this is a real cheddar bob fest.