Tatum O’Neal and John McEnroe, 1986

Daughter of actor Ryan O’Neal, Tatum O’Neal was the youngest actress to win an Academy Award for her performance as Addie Loggins in Paper Moon (she won the award at the age of 10!). In 1986, she married John McEnroe, a popular tennis player. O’Neal channeled her inner American princess in an ever-flowing high neck gown complete with a crown of flowers and baby’s breath during the star-studded ceremony at St. Dominic’s Church in upstate New York.

After plenty of publicized ups and downs, Hollywood’s golden child and the cunning foul-mouthed tennis player divorced in 1994. O’Neal infamously struggled with depression and addiction, before and after her marriage. She has since recovered and lives a happy life with her children and even wrote a tell-all book about her troubled life and rocky relationship with McEnroe titled A Paper Life.