The Woolaroc collection includes a broad representation of paintings by many of the "Old Masters" of western art, such as: Frederic Remington, Charles M. Russell, William R. Leigh, Frank Tenney Johnson, Thomas Moran and many others.
Also represented are more contemporary artists such as Wilson Hurley, John Clymer, Clark Hulings, and Bettina Steinke. Five of the original six Taos Society Artists are represented: O.E. Berninghaus, E.I. Couse, Herbert Dunton, Bert Phillips, and J.H. Sharp.
Much of the collection was personally acquired by Frank Phillips during his lifetime and has since been greatly enhanced by donations from other members of the Phillips family. The more recent additions include works by many leading contemporary western artists and various landscape artists, including an exquisite work by Albert Bierstadt.
The Woolaroc sculpture collection also includes pieces by many of the greats of western artists, including Remington and Russell. In addition, the 12 bronzes that were entered in the 1927 Pioneer Woman contest, created by the best sculptors of the day, are prominently displayed in the collection.
Heroic-sized sculptures by Bryant Baker and Jo Mora are located both inside and outside the Woolaroc Museum, where they illustrate the history of Oklahoma and the American West.
Works by contemporary sculptors such as Harry Jackson, Joe Beeler and John D. Free also grace the Woolaroc collection. Woolaroc also displays a complete collection of the sculptures of Joe Beeler, including two heroic-sized pieces on the Woolaroc grounds.