- Was reportedly very good friends with producer Joseph M. Schenck and his wife, actress Norma Talmadge. Schenck reportedly approved of their frequent on-screen pairings and off-screen friendship because of O'Brien's well-known homosexuality. Still, in later years O'Brien claimed to have at one point had an affair with Talmadge. O'Brien and Talmadge made seven features together.
- O'Brien's career as leading man in the 20s faded with his receding hairline.
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