At 17 Howard's interest in flying was sparked when he saw a band of gypsy fliers performing in their flying circus. By 18 he had saved up enough cash to buy an OX-5 powered Standard biplane. In those days learning how to fly was often self taught and Howard thought he was up to it. The Standard was a safe plane and he seemed to be learning fine when while flying was unable to pull out of a spin, crashed breaking his leg and writing off the plane, as well.
Howard moved to Dallas and started working in the Curtiss Aircraft factory. The pay was not as good as what others jobs paid but what he learned about design and construction of aircraft was worth more than money. Over the next few years he tinkered with aircraft design using spare parts to build his first plane, later called the DGA.His second attempt at aircraft design was at the request of a Houston bootlegger, who dubbed the resulting "rum-runner" a "Darned Good Airplane," giving it and future Howard aircraft their trademarked initials of DGA.
In his plane Pete, Howard won five air races. As competition increased, he and his partner, Gordon Israel, built two larger, low-wing, wire-braced monoplanes, Mike and Ike. Ike was particularly quick in flying in an inverted position, and for a time held the world record for inverted speed. His sixth plane was called Mister Mulligan. It placed in competition for several pilots before it was destroyed in an accident in the 1936 New York - Los Angeles Bendix Transcontinental Race, a propellor failure costing Howard both the plane and his leg. Mister Mulligan's fame led to the DGA-8 and the DGA-9 as well as the 1937 formation of the Howard Aircraft Corportaion, which ran until 1944.
The first Douglas DC-3 aircraft were ordered by American Airlines (1935) and powered by Wright Cyclone engines. Soon after, United Air Lines ordered the DC-3, but specified Pratt & Whitney Twin Wasp engines. Benny Howard was dispatched to Douglas to oversee the installation of the new engine. His career at Douglas continued for many years, including piloting the initial tests of the DC-4E, A-26 Invader, and DC-6 aircraft. He also served as test pilot on the Budd RB-1 Conestoga and other aircraft. He was elected an Honorary Fellow of SETP.