9. Jack McDowell
The New Job: Musician
Jack McDowell was a MLB pitcher. He began his career with the Chicago White Sox, and won the 1993 American League Cy Young award while with the team. While he was lighting it up on the mound for the White Sox, Jack was also in a band with a couple of other MLB players called V.I.E.W. Following the conclusion of his playing career, Jack turned to music again, forming another band called stickfigure.