Sylvester Stallone and Jennifer Flavin: 22 years
Stallone, 72, and Flavin, 50, have been married since 1997. They first met in 1988, but Stallone ended the relationship in 1994 after having an affair with Janice Dickinson. They reconciled in 1995 and now have three daughters: Sophia Rose, Sistine Rose, and Scarlet Rose.