Ridin' Dirty refers to a game played between friends where points are earned for successfully having sexual intercourse with disgusting and extremely obese women. Pictures must be taken with the whale to prove that sexual intercourse actually took place. These women only qualify if their obesity is comparable to the fat women featured in Spencer's gag cards. The winner receives a pre-set prize, typically money.
The Chamillionaire song "Ridin'" was created to commemorate a specific instance where the artist won this game by sexually pleasuring a morbidly rotund transvestite. This event led to additional (bonus) points for Chamillionare which gave him a solid lead and eventually a win in a game between him and his friends.
—(according to Fag Dictionary)
The official theme song
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