Judy Garland
Judy Garland, renowned for her role in The Wizard of Oz, embarked on five marriages throughout her life. Her first journey down the yellow brick aisle was with Scarecrow David Rose in 1941. She then found love with her Tin Man, director Vincente Minnelli, with whom she had a famous daughter, Liza.
Interestingly, Minnelli himself had experienced four marriages. Garland's next partner was her Cowardly Lion, Sidney Luft. Her fourth husband was the Wizard Mark Herron, while the man behind the curtain for her fifth and final marriage was Mickey Deans.