Alcatraaaz

Alcatraaaz is a famous gangster rapper who Bart likes. He went to the point of sneaking out to see one of his concerts.

History
Alcatraaaz was the headline act for the Murder 4 Life concert, which Bart wanted to go to. Bart managed to sneak to the concert and got right to the stage when Alcatraaaz dropped his microphone. Bart picked it up and Alcatraaaz told Bart to put it down unless he knew how to use it. Bart then got up on stage and rapped alongside Alcatraaaz. After the concert, Alcatraaaz invited Bart to go with him in his limo, which had a wax museum downstairs. He then dropped Bart back off at his house.

When Lisa and Principal Skinner were trying to work out where Bart actually was the night of the concert, they went to Alcatraaaz's mansion and asked to view footage of the concert. Alcatraaaz let them do so on the TV in his shoe closet. When Homer, Chief Wiggum and Bart all come in, Homer accidentally knocks the TV off the wall and all of Alcatraaaz's gang point guns at them. Alcatraaaz cools down the situation and throws a house party.

At the house party, Skinner asked Alcatraaaz if there was a place for a "forty-something elementary school administrator" in the hip-hop world. Alcatraaaz told him there was, but Superintendent Chalmers already filled that role.

He attended Jay G's party at his mansion.

Behind the Laughter
Alcatraaaz's name is a reference to the prison.

An archive image of Alcatraaaz's rap concert Bart attended in "Pranksta Rap" was seen in the couch gag for "Looking for Mr. Goodbart".