Jon Stewart & Tracey McShane

Jon Stewart is a familiar face on TV for being the host of the 16-time Emmy Award-winning program The Daily Show. After getting his degree from The College of William and Mary in Virginia, Stewart pursued a comedy career. In 1999, The Daily Show came into being, and it became the highlight of the comedian’s career. In 2000, he married Tracey McShane after dating for four years.

Stewart’s proposal to McShane was one for the books as he created a personalized crossword puzzle with Will Shortz’s help. Shortz was the crossword editor at the New York Times. The puzzle that the two created spelled out the proposal, much to the delight of McShane. They have two children, a cat and a dog. Though Stewart is no longer part of The Daily Show, his role as a father and a husband trumps every job that he has taken on since then.