8 Hip-Hop Stars Taylor Swift Could Not Deny Her Love For

Chance the Rapper posted this photo with Taylor in July when her 1989 world tour stopped in Chicago. "Dear Taylor, Chicago loves you and you're welcome back anytime," he wrote. "Congrats on 2 back to back sold out nights at Soldier's Field of 55,000 people, and thanks for treating my friends so well." Their friendship came as a bit of a surprise for some fans, but it just goes to show that you should never underestimate Taylor's underground hip-hop connections.