Sylvester Stallone & Jennifer Flavin – 23 Years

Sylvester Stallone once had to sell his dog and star in adult videos because he was flat broke. We all know he stopped doing adult films, and after selling the screenplay for Rocky, he turned his career around and even bought the dog back. His relationship with Jennifer Flavin has had similar ups and downs.

In the ’90s, the relationship was on-again-off-again, with Stallone at one point leaving Flavin, via FedEx no less. But it turns out it was because he thought model Janice Dickinson was pregnant with his child, and when he found out that she wasn’t, he went back to Flavin, whom he married in 1997.

Oliver Hudson & Erinn Bartlett – 16 Years

At around the same time when Erinn Bartlett played in the Raising Helen movie, she also announced her engagement to Oliver Hudson, Goldie Hawn’s son and a famous actor. In 2006 they exchanged vows and have been happily married ever since, even having three children together, two sons and a daughter.

Erinn may not have acted since 2013 when she played on an episode of Rules of Engagement, but Hudson, on the other hand, has never stopped! He was playing on the Splitting Up Together series until 2019. According to his IMDb page, he’s now going to play on a movie called The Three of Us.