Dre vs. Diddy: Who'd You Rather? Dre vs. Diddy Who'd You Rather? Published May 27, 2010 6:09 PM PDT | Updated May 12, 2019 12:58 PM PDT Music moguls Dr. Dre, 45, and Diddy, 40, united at an event in NYC on Wednesday. Question is ... Share on Facebook Share on X See also Jodie Foster vs. Cynthia Nixon -- Who'd You Rather? Simpson vs. Simpson: Who'd You Rather? Rhoda vs. Alice: Who'd You Rather? Diddy Dr. Dre Who'd You Rather? Music