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In 1918, Chaplin started work for First National and Loyal Underwood was on hand. He was credited and appeared in all seven First National Shorts which Chaplin directed.
Underwood was a short man. Next to the short Chaplin at 5 ft 5 in (165 cm), he appeared puny and weak. Hence, the comedy of a situation in which such a man is the antagonist; Chaplin's character routinely shrugged him off.
Between 1921 and 1927, Underwood appeared in several other lesser known films. In the next twenty years, he was again appearing uncredited in films, such as Arizona Bad Man, Let's Dance and The Paleface.
Underwood's final film was a credited role, albeit a small one, as a Street Musician in Chaplin's final American film Limelight in 1952.
Underwood died in Los Angeles on September 30, 1966 in Southern California, and is buried in the Sheltering Hills section at Forest Lawn - Hollywood Hills Cemetery in Los Angeles, California. He was 73. Decades after his death, he lies in a still-unmarked curbside grave.
- Limelight (1952) as Street Musician
- The Pilgrim (1923)
- My American Wife (1922)
- The Man Who Woke Up (1921 - writer)
- A Day's Pleasure (1919)
- The Professor (1919)
- Sunnyside (1919)
- Shoulder Arms (1918)