Jazzy James

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Jazzy James
Jazzy James.png
Character Information
Male ♂
Hair: Brown
Occupation: Current: Stall owner
Former: Rapper/songwriter
First Appearance: "The Great Phatsby: Part One"
Voiced by: Keegan-Michael Key

Jazzy James is a former rapper and songwriter and former member of the rap group The Five Boyfriends. He currently owns the stall Elite Candles.


Bart met Jazzy James when he was running his stall. James said he had some information about Jay G and would tell Bart it if he bought a candle, the cheapest of which was $55. Bart refused and left.[1]

When getting some history about Jay G from Milhouse, Milhouse shows Bart, Homer and Mr. Burns an album by The Five Boyfriends. Bart recognized Jazzy James from the cover and Milhouse told them that James wrote all the songs for The Five Boyfriends. Bart, Homer and Burns then ask Jazzy James for help bringing Jay G down.

Jazzy James tried to rap a song about Jay G but couldn't because he had lost his spark. After they dangle James from the window of the record studio, he writes a decent rap which he then records. RZA, Snoop Dogg and Common all join in on the rap too and they put together a full song to bring Jay G down.

At the release of the song, it is found out that Jay G bought the master recording from everyone who made it, including Jazzy James, because Jay G is the best producer in the world.[2]