Although it seems like Kanye has been at the barrel of the gun in two of his most public breakups, (Alexis Phifer and Amber Rose). Kanye defends himself and says that he has left plenty of pretty girls, casting a gloomy shadow over their reputation.
Considering that in the previous line he’s talking about reputation through media repercussion, makes more sense a possible reference to the VMAs incident. Taylor Swift is a pretty girl, and guaranteed he left her sad. Because the next line refers to Brad Pitt and Jennifer Anniston, Kanye could also be putting himself on line with the “bad boy heartbreakers” of Hollywood
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