7. Helena Christensen
After he stopped filming in Titanic, the gorgeous Helena Kept him hot following the iceberg struck. They had a short fling in 1997. The Danish model and beauty queen was one of those original Victoria’s Secret Angels. If she’s an Angel, then Leo needed to get along with her. We’d jump on that also. She was certainly the start of Leo’s Angels club. Now she’s among the hottest MILFs ever.