Early work '' (1937) Finding himself penniless, Brennan began taking parts as an extra in films at
Universal Studios in 1925, starting at $7.50 a day, equal to $ today. He wound up working at Universal off and on for the next ten years. His early appearances included
Webs of Steel (1925),
Lorraine of the Lions (1925) and
The Calgary Stampede (1925), a
Hoot Gibson Western. Brennan was also in
Watch Your Wife (1926),
The Ice Flood (1926),
Spangles (1926),
The Collegians (1926, a short),
Flashing Oars (1926, a short),
Sensation Seekers (1927), ''
Tearin' Into Trouble (1927), The Ridin' Rowdy (1927), Alias the Deacon (1927), Blake of Scotland Yard (1927) (a serial), Hot Heels (1927), Painting the Town (1928) and The Ballyhoo Buster'' (1928). The latter was directed by
Richard Thorpe who would use Brennan as an extra several times on films. Brennan had minor roles in
The Racket (1928) from
Howard Hughes,
The Michigan Kid (1928),
Silks and Saddles (1929),
The Cohens and the Kellys in Atlantic City (1929) and ''
Smilin' Guns (1929) and The Lariat Kid'' (1929) with Gibson. He also worked as a stand in. Brennan was in
His Lucky Day (1929),
Frank Capra's
Flight (1929),
One Hysterical Night (1929) (a bigger role),
The Last Performance (1929),
The Long Long Trail (1929) with Gibson and
The Shannons of Broadway (1929). Other Brennan appearances included
Dames Ahoy! (1930),
Captain of the Guard (1930),
King of Jazz (1930) (Brennan said he played nine parts but when he saw the film "I sneezed and I missed myself"), Goldwyn mostly loaned out Brennan's services to other studios. MGM put him in
West Point of the Air (1935). He was reunited with Whale in
Bride of Frankenstein (1935), in which he had a brief speaking part and also worked as a stuntman. Brennan's parts remained small in
Party Wire (1935),
Spring Tonic (1935),
The Gay Lady (1935),
Man on the Flying Trapeze (1935) and
Welcome Home (1935). He did a short,
The Perfect Tribute (1935) and was in George Stevens'
Alice Adams (1935), but his scenes were deleted. He could be seen in ''
We're in the Money (1935) and She Couldn't Take It'' (1935).
Move to supporting actor Brennan finally earned significant roles with a decent part in Goldwyn's
Barbary Coast (1935), directed by
Howard Hawks and an uncredited
William Wyler. "That really set me up", Brennan said later. Brennan had his first lead role in
Affairs of Cappy Ricks (1937) at
Republic Pictures. He followed it with the co-starring part in Fox's
Wild and Woolly (1937), billed second after
Jane Withers. He was in
The Buccaneer (1938), directed by
Cecil B. DeMille. Brennan portrayed town drunk and accused murderer Muff Potter in
The Adventures of Tom Sawyer (1938). Brennan followed it with
The Texans (1938), ''
Mother Carey's Chickens'' (1938) and Goldwyn's
The Cowboy and the Lady (1938) with
Gary Cooper – the first time Brennan played Cooper's sidekick.
Second Oscar: Kentucky (1938) Brennan won his second Best Supporting Oscar for
Kentucky (1938), a horse racing film from
20th Century Fox with
Loretta Young. He supported
Fred Astaire and
Ginger Rogers in
The Story of Vernon and Irene Castle (1939). Brennan also appeared in
Melody of Youth (1939), and
Stanley and Livingstone (1939) at Fox. Instead Brennan was top-billed in Fox's
Maryland (1940), an attempt to repeat the success of
Kentucky. Brennan said he had been working constantly since Christmas 1937. "I'm just plain punch drunk", he said.
Third Oscar: The Westerner (1940) Brennan had one of his best roles in Goldwyn's
The Westerner (1940), playing the villainous
Judge Roy Bean opposite Gary Cooper. William Wyler directed and the film earned Brennan his third Best Supporting Actor Oscar within a five-year span. Goldwyn bought
Trading Post as a vehicle for Brennan, but the film never materialized. Brennan next supported
Deanna Durbin in
Nice Girl? (1941) and then Cooper again in
Frank Capra's
Meet John Doe (1941) and Hawks'
Sergeant York (1941), a role that earned Brennan a fourth Oscar nomination. He could also be seen in
This Woman is Mine (1941) as a sea captain. Brennan played the top-billed lead in
Swamp Water (1941), the first American film by director
Jean Renoir. He appeared in
Rise and Shine (1941) and then played reporter Sam Blake in
Pride of the Yankees (1942). Brennan appeared in the war films
Stand By for Action (1942) and
Hangmen Also Die! (1943), in which he played a Czech professor. He also appeared in
Slightly Dangerous (1943),
The Last Will and Testament of Tom Smith (1943) and Goldwyn's Russian war epic
The North Star (1943). He was top-billed in a follow-up to
Kentucky and
Maryland at Fox,
Home in Indiana (1944). Brennan was particularly skilled in playing the sidekick of the protagonist or the "grumpy old man" in films such as Hawks'
To Have and Have Not (1944). Brennan was a comic pirate in the
Bob Hope film
The Princess and the Pirate (1944). He was teamed with John Wayne for the first time since both men had obtained stardom in
Dakota (1945), directed by
Joseph Kane. He supported
Bette Davis in
A Stolen Life (1946) and appeared in the Fox musical
Centennial Summer (1946).
Western roles Brennan returned as a villain as
Old Man Clanton in
John Ford's
My Darling Clementine (1946), opposite
Henry Fonda. He followed this with parts in
Nobody Lives Forever (1946) at Warner Bros. and
Republic's
Driftwood (1947). He appeared in another Americana film at Fox,
Scudda Hoo! Scudda Hay! (1948), and then in one of the greatest films in his career,
Red River (1948), playing John Wayne's sidekick. After supporting
Robert Mitchum in
Blood on the Moon (1948), he played another kindly father role in
The Green Promise (1949). Brennan was billed second to
Rod Cameron in
Brimstone (1949), and he supported Gary Cooper in
Task Force (1949). Brennan focused on Westerns:
Singing Guns (1950),
A Ticket to Tomahawk (1950),
Curtain Call at Cactus Creek (1950),
The Showdown (1950),
Surrender (1950),
Along the Great Divide (1951),
Best of the Badmen (1951) and
Return of the Texan (1952). He appeared in the war films
The Wild Blue Yonder (1951) and
Lure of the Wilderness (1952), a remake of
Swamp Water in which he reprised his role, although with less screen time than in the original film. Brennan was in
Sea of Lost Ships (1953) with
John Derek,
Drums Across the River (1954) with
Audie Murphy,
The Far Country (1954) with
James Stewart and
Four Guns to the Border (1954) with
Rory Calhoun. He also appeared in
Bad Day at Black Rock (1955) for MGM. ==Later work==