JON STEWART AND TRACEY MCSHANE – 20 YEARS

Widely recognized for hosting The Daily Show from 1999 to 2015, Jon Stewart garnered twenty Primetime Emmy Awards as either producer or writer. He began as a stand-up comedian but ventured into the silver screen with film and television credits in Half Baked, The Faculty, and Evan Almighty.

While filming the movie Wishful Thinking, a production assistant arranged for a blind date between the host and Tracey Lynn McShane. The pair dated for four years and exchanged vows in 2000. We really love the way he popped the question! With the assistance of crossword editor Will Shortz, Stewart made a personalized crossword puzzle. The puzzle included clues about marriage, which McShane solved eventually. In June 2001, the couple filed a joint name change application and changed their last names to Stewart. They welcomed two lovely kids via in vitro fertilization.