Sheryl Crow
Sheryl Crow almost had a completely different life as a St. Louis schoolteacher with a devout fiancé who demanded she sing exclusively for God. In 1984, the University of Missouri grad left him and moved to LA to pursue secular music. The former Michael Jackson back-up singer strummed her way onto the charts solo with her 1993 folk-rock album Tuesday Night Music Club, which lead to two Top 5 singles "All I Wanna Do" and "Strong Enough," three Grammys and more than 7 million sales. Her 1996 sophomore effort accrued two more Grammys and she took the tunes on the road as part of the all-girl festival Lillith Fair. She gave acting a try in 1999's "The Minus Man," which starred future beau Owen Wilson. The "If It Makes You Happy" and "Soak Up The Sun" singer became very active in ecological issues, performers' rights, founding the Recording Artists' Coalition, and cancer charities especially after fighting breast cancer at 44 and finding a benign brain tumor in 2011. After Lance Armstrong said the pressure of her biological clock ended their engagement in 2006, she adopted sons Wyatt (2007) and Levi (2010). She's currently dating music producer Doyle Bramhall II who was part of her touring band.