7. Drake – “Taylor Made Freestyle”
Drake was using this record to bait Kendrick Lamar into responding to “Push Ups.” Following the release of that record, Lamar would take three weeks to release his next diss track, and Drake tried to used that to his advantage. He ridiculed Kendrick for going radio silent and claimed Taylor Swift was his boss and forced him not to drop anything since she was releasing her new album, The Tormented Poets Department.
However, Drake pulled a risky move using artificial intelligence to craft fictional bars from Snoop Dogg and the late Tupac Shakur to get at Kendrick. The idea was extremely clever given that Snoop passed the West Coast torch to K. Dot at a show a few years ago, and Pac is one of his biggest inspirations. However, it’s hard to give Drake a pass on this one as AI is still a red flag for many, especially in hip-hop culture when fans turn a side-eye to anything that’s deemed fake.
“Taylor Made Freestyle” was eventually pulled from streaming services after Shakur’s estate threatened to sue Drake. He later used that as ammo on “Family Matters” to claim Kendrick was the one who told the estate to get the song taken down.


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