Michael Bolton and Paula Abdul
Bolton, who was friends with Abdul's older sister, babysat Abdul when she was 7, and the straight up truth is that he, well, sucked (outside of the singing her to sleep part). "He would only want to just jam with the other musicians in the building I lived in," Abdul told Jimmy Kimmel in 2011. One time, when Bolton went outside, Abdul got a pencil, which was stuck in the couch, jammed in her knee and had to be taken to the hospital. Years later, when they both hit it big, Bolton asked Abdul to choreograph his tour. The crooner also Skyped into the Kimmel interview to confirm that he indeed babysat the "adorable" American Idol judge, but his memory of the pencil incident is a little hazy. "She's confusing that with ice cream," he joked.