Britney Spears and Jason Alexander: 55 Hours

In 2004, singer Britney Spears married her childhood friend, Jason Alexander. Her marriage to Alexander is perhaps, the shortest on this list and one of the shortest in the country as it only lasted 55 hours. In a podcast called “Toxic: The Britney Spears Story,” Alexander revealed that Spear’s team made him sign an annulment so they could continue their relationship.

Her mother, Lynne, also played a negative role in her daughter’s first marriage and forced them to end it. Spears then got married to Kevin Federline the same year, but it didn’t work out, and in 2021, she is engaged to her long-time boyfriend, Sam Asghari.