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* NeverLiveItDown: Winning that "Best Rap Album" Grammy over ''[[Music/GoodKidMAADcity good kid, m.A.A.d city]]''. Even if he obviously had no say over that decision and he vocally disapproved of it, in retrospect it is still seen as something that completely changed the course of his public image. Many critics have noted that his post-Grammy music made a conscious attempt to address the backlash by being more self-flagellating and explicit about racial issues in a way that actually worked against him: His DarkerAndEdgier tone and unflinching acknowledgment of racism alienated the pop crowd, but his constant lyrical focus on trying to navigate racial issues alienated the conscious hip-hop crowd, who felt that he was becoming self-indulgent and had lost the balance between the uplifting pop and serious messages that had made him famous.
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* NeverLiveItDown: Winning ''The Heist'' winning that "Best Rap Album" Grammy over ''[[Music/GoodKidMAADcity good kid, m.A.A.d city]]''. Even if he obviously had no say over that decision and he vocally disapproved of it, in retrospect it is still seen as something that completely changed the course of his public image. Many critics have noted that his post-Grammy music made a conscious attempt to address the backlash by being more self-flagellating and explicit about racial issues in a way that actually worked against him: His DarkerAndEdgier tone and unflinching acknowledgment of racism alienated the pop crowd, but his constant lyrical focus on trying to navigate racial issues alienated the conscious hip-hop crowd, who felt that he was becoming self-indulgent and had lost the balance between the uplifting pop and serious messages that had made him famous.
