Late-night TV staple David Letterman waited until age 56 to take the parenthood plunge when he and his longtime girlfriend and now wife, Regina Lasko, had son Harry in 2003. Letterman noted the advantages of being an older dad when he announced the big news on his show. "By the time the child has trouble in life, you know, I'll be dead. I'll be long gone. By the time the kid's out stealing cars, you know, Dad will be dead a few years."