Sylvester Stallone & Jennifer Flavin – Married Since 1997

Although Sylvester Stallone and Jennifer Flavin experienced a rocky start in their relationship, they’re proof that true love triumphs in the end. The couple met at the height of the “Rocky” star’s career in the ’80s, dating on and off until a DNA test proved he wasn’t the father of his ex Janice Dickinson’s child.

And so, Stallone and Flavin wed in 1997 and went on to raise three daughters together. Still happy, the pair left California for Florida and bought a $35 million home in the latter part of 2020. They then put their Beverly Hills residence for a whopping $110 million.