Matthew McConaughey

Matthew McConaughey got his biggest break when he landed the lead role for A Time to Kill. In this movie, he dated two of his co-stars, starting with Ashley Judd, and later on, Sandra Bullock, who are now both A-listers in their own rights. He later dated another co-star, the Spanish beauty, Penelope Cruz, whom he worked with within the movie Sahara. Though there was a bit of a language barrier, the two fell in love.

However, because of their busy schedules, the couple decided to call it quits. It was also the same year when he met Camila Alves in a bar, and it was over for him. The two dated after three days of their first meeting and they are now happily married with three children. McConaughey’s net worth and investments can easily keep him and his new family comfortable in the years to come.