Charlie Sheen comes from a famous family - and he's passing on the torch to daughters Cassandra Estevez, Sami Sheen and Lola Sheen, and twin sons Bob and Max Sheen. The Two and a Half Men alum became a father for the first time in 1984 when he welcomed Cassandra with his high school sweetheart, Paula Speert. Their relationship came full circle in 2010 when Charlie walked his eldest daughter down the aisle to wed her own childhood sweetheart, Casey Huffman. Three years later, Charlie became a grandfather when Cassandra and her husband welcomed their daughter, Luna.