Aaliyah and R. Kelly: 4 Months
R&B singer, R. Kelly married the late singer, Aaliyah at the Sheraton Gateway Suites in Rosemont, Illinois in 1994. But they had to keep their wedding a secret because Aaliyah was only 15 at the time. Things didn’t work out, and she had the marriage annulled in 1997, citing that she had lied about her age. She reportedly cut all ties with him after that.