His dad is appreciating his music presumably as much as his Shakespeare recitals.
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Word play on “think” makes these lines great. He going to stop overthinking, but won’t stop drinking.
Skiz cared more about rapping than what had happened the previous night.
Skizzy got drunk and when he woke up, his friends told him what had happened the previous night
Sabrina the Teenage Witch was a series that aired from 1996-2003. References to previous line about loving a mystery. She would act weird on the show to hide her magic from her friends.
A reference to the retired basketball player, Dikembe Mutombo. Mutombo was so big that he accumulated several injuries that contributed to the end of his career.