Sylvester Stallone
Sylvester Stallone was married to first wife Sasha Czack from 1974 to 1985, and they had two kids. Czack was 35 when he left her for model and actress Brigitte Nielsen (pictured left,) who was 22 when she married Stallone in 1985. Nielsen and Stallone were married for two years. He and Nielsen divorced in 1987, and almost immediately after the ink dried on that split, Stallone took up with current wife Jennifer Flavin (pictured right,) who was just 19 at the time. He and Flavin have been together, save for a brief split, ever since.
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