Date: February 2010

What happened? A month before Wayne started his eight-month prison sentence in March 2010, Drizzy told Rolling Stone, “I don't think there will be anybody like Lil Wayne ever again in hip-hop. He paralyzes a room when he walks into it, his wordplay, the excitement that he brings to his music."

Complex says: Drizzy was missing his good buddy before he even said goodbye. We agree, Wayne’s legacy is already cemented, but freezing up when he walks in the room? Drizzy’s got it bad.