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Alcatraaz is a famous gangsta rapper whom Bart likes so much that he went to the point of sneaking out to see one of his concerts. His name is derived from a notorious prison.


While performing at his concert, Alcatraaz drops a his microphone. As it lands in Bart's hands, he grabs it, then climbs onto the stage and challenges Alcatraaz to a rap battle. After the concert, Alcatraaz gives Bart a ride home in his limousine, along with a jersey.

Later on, Skinner asks Alcatraaz if there is any place in the rapping world for a "forty-something elementary school administrator." Alcatraaz says he already hired a man for that job, Superintendent Chalmers.

Alcatraaz also makes a small appearance in the church in "Milhouse of Sand and Fog".

Alcatraaz recently appeared in The Simpsons: Tapped Out as a character during Act 3 (Hip Hop) of the Homerpalooza 2017 event.