After golf, oil painting was Eisenhower's second hobby. While at Columbia University, Eisenhower began the art after watching Thomas E. Stephens paint Mamie's portrait. Eisenhower painted about 260 oils during the last 20 years of his life to relax, mostly landscapes but also portraits of subjects such as Mamie, their grandchildren, General Montgomery, George Washington, and Abraham Lincoln. Wendy Beckett stated that Eisenhower's work, "simple and earnest, rather cause us to wonder at the hidden depths of this reticent president". A conservative in both art and politics, he in a 1962 speech denounced modern art as "a piece of canvas that looks like a broken-down Tin Lizzie, loaded with paint, has been driven over it."

What was Eisenhower's favorite hobby other than golfing?