Sean Penn
While filming the video for Material Girl in 1985, Madonna fell for actor Sean Penn and following a whirlwind romance, the pair married later that year.
Reports suggesting problems in the relationship were rife soon after, however, and after Penn initially filed then withdrew divorce papers in 1987, they split on New Year's Eve 1988 - the divorce coming through a year later.
Speaking about her marriage to Penn, Madonna admitted: 'I was completely obsessed with my career and not ready to be generous in any shape or form.'