Henry has appeared in more than 40 films including The Graduate, Candy, Catch-22, Taking Off, The Man Who Fell to Earth, Gloria, Eating Raoul, Aria, Tune in Tomorrow, Defending Your Life, The Player, and Grumpy Old Men. He co-directed Heaven Can Wait, the 1978 remake of Here Comes Mr. Jordan, and appeared in the film as an officious angel, reprising the character originally played by Edward Everett Horton.