David Letterman & Regina Lasko | 35 Years

They were together for over two decades before they even decided to get married. We can understand why David Letterman may have been hesitant to do so; after all, he had already gotten through one failed marriage with his college girlfriend in the ‘70s. Nevertheless, he met Regina Lasko in 1986 and hasn’t looked back since.

Lasko has worked as a production manager on shows like Another World, as well as Late Night with David Letterman. In the meantime, David is currently hosting My Next Guest Needs No Introduction with David Letterman. They had one son together in 2003. So far, Letterman alone is estimated to be worth $400 million.