Carey (not to be confused with baseball announcer Harry Caray) appeared in many classic Westerns directed by John Ford (a favorite of Bob Gale and Robert Zemeckis). A respected character actor, like his father, Harry also acted in a large number of Western genre films. They both appeared in the acclaimed 1948 film, Red River, though they never shared a scene. Harry Jr. served with the United States Navy during World War II. In addition to Red River, Carey made three more films with acclaimed film director Howard Hawks: Monkey Business (1952), Gentlemen Prefer Blondes (1953), and Rio Bravo (1959).
Harry also made 10 movies with John Wayne, starting with Red River and ending with Cahill U.S. Marshal (1973). Carey, along with Wayne, was cast by Ford in She Wore A Yellow Ribbon (1949) Rio Grande (1950), and The Searchers (1956).
Carey appeared in Tales from the Set, a series of video interviews about various people he had worked with during his career. The series debuted at the Epona Festival, a festival devoted to horses, in France, October 11-14th, 2007. Subsequently it has appeared for sale in download links on various fan websites and Amazon.
In 2009, Carey and his partner Clyde Lucas completed Trader Horn: The Journey Back, a remembrance of Carey's father's adventure film of the 1930s. The younger Carey had at age 8 accompanied his father to Africa for the filming of Trader Horn, the first major studio motion picture filmed in Africa.
After 53 years as an actor, Carey attempted his first writing and producing project with a feature called Comanche Stallion, a western fantasy film that John Ford had considered making in the early 1960s, based on the 1958 book by Tom Millstead. Participating actors reportedly included James Arness, Rance Howard, and Robert Carradine.