Highly regarded by Bette Davis, he became her most frequent male co-star, appearing with her in 13 films, including Front Page Woman (1935), Special Agent (1935), The Golden Arrow (1936), Jezebel (1938), The Old Maid (1939), Dark Victory (1939), and The Great Lie (1941). Brent also played opposite Ruby Keeler in 42nd Street (1933), Greta Garbo in The Painted Veil (1934), Ginger Rogers in In Person (1935), Madeleine Carroll in The Case Against Mrs. Ames (1936), Jean Arthur in More Than a Secretary (1936), Myrna Loy in Stamboul Quest (1934) and The Rains Came (1939), Merle Oberon in 'Til We Meet Again (1940), Ann Sheridan in Honeymoon for Three (1941), Joan Fontaine in The Affairs of Susan (1945), Barbara Stanwyck in So Big! (1932), The Purchase Price (1932), Baby Face (1933),The Gay Sisters (1942), and My Reputation (1946), Claudette Colbert in Tomorrow Is Forever (1946), Dorothy McGuire in The Spiral Staircase (1946), Lucille Ball in Lover Come Back (1946), and Yvonne De Carlo in Slave Girl (1947).