Billy Ray and Tish Cyrus – 38 years

Billy Ray Cyrus’s record company told him not to do it, but he didn’t care–he was going to marry Tish Finley no matter what anyone said. At the time in 1993, Tish was pregnant with their second child, famous pop singer Miley Cyrus. She also had two children from a previous marriage, Trace and Brandi, who Billy Ray treated as his own.

Sadly, the couple has gone through some very public ups and downs. In 2010, Billy Ray and Tish filed for divorce but decided to stay together in 2011. Then Tish filed for divorce again in 2013. Luckily, the couple went through months of therapy and decided to stay together after all, and it looks like it paid off.