Inspired by his Geologist Father, Headington founded Headington Oil in 1978. He stayed under the radar until 2008 when he sold acreage in North Dakota's Bakken oil play to XTO Energy for $1.85 billion.
He produced Angelina Jolie's feature directorial debut, In the Land of Blood and Honey, which was Golden Globe nominated for Best Foreign Language Film; as well as the recipient of the Stanley Kramer Award and the NAACP Image Award for Outstanding Foreign Motion Picture in 2012.
Headington was honored in November 2013 as an inductee to the Oklahoma Hall of Fame.