Chess Masterson is the self-proclaimed name given to Freddie's disguise in iParty with Victorious. Along with Sam and Carly (and Gibby), the makeup was applied so that no one would recognize the iCarly gang in their undercover mission to spy on Steven Carson, Carly's two-timing boyfriend. The makeup job was done by Spencer's ex-girlfriend Moni in Los Angeles. Later, he peels off his "Chess Masterson" makeup.
The name Chess Masterson could possibly reflect Freddie's somewhat nerdy personality, because it could mean he is a master at the game of chess.
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