David Letterman plans to retire in 2015. Lettermans longtime rival Jay Leno left The Tonight Show (again) earlier this year, leaving many to wonder when Letterman would decide to walk away. We dont have the timing for this precisely down, Letterman told his audience. I think it will be at least a year or so, but sometime in the not too distant future, 2015 for the love of God, in fact, Paul and I will be wrapping things up. Letterman received a standing ovation as he shared news of his pending retirement.