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From 1909 to 1927, Howland appeared on Broadway in musicals, occasionally performing in silent films. The musicals include ''[[Leave It to Jane]]'' (1917), ''[[Two Little Girls in Blue]]'' (1921) and ''[[Wildflower (musical)|Wildflower]]'' (1923). He was in the film ''[[Janice Meredith]]'' (1924) with [[Marion Davies]]. With the advent of sound films, his theatre background proved an asset, and he concentrated mostly on films thereafter, appearing in nearly two hundred movies between 1918 and 1958.
Howland often played eccentric and rural roles in Hollywood. His parts were often small and uncredited, and he never got a leading role. He was a personal favorite of [[David O. Selznick]],{{citation needed|date=March 2017}} who cast him in his movies ''[[Nothing Sacred (film)|Nothing Sacred]]'' (1937) as a strange luggage man, ''[[The Adventures of Tom Sawyer (1938 film)|The Adventures of Tom Sawyer]]'' (1938, as the teacher Mr. Dobbins) and ''[[Gone with the Wind (film)|Gone with the Wind]]'' (1939) as a carpetbagger businessman.<ref name="bio">{{cite web |url=https://www.nytimes.com/movies/person/33602/Olin-Howland/biography |archive-url=https://web.archive.org/web/20140422000718/http://www.nytimes.com/movies/person/33602/Olin-Howland/biography |url-status=dead |archive-date=April 22, 2014 |department=Movies & TV Dept. |work=[[The New York Times]] |author=Hal Erickson |author-link=Hal Erickson (author) |date=2014 |title=Olin Howland |access-date=February 3, 2016 }}</ref> He also played in numerous westerns from [[Republic Pictures]], including the [[John Wayne]] films ''[[In Old California (1942 film)|In Old California]]'' (1942) and ''[[Angel and the Badman]]'' (1947). As a young man, Howland learned to fly at the [[Wright Flying School]] and soloed on a [[Wright Model B]]. This lent special
He also played in television shows during the 1950s. One of Olin's memorable television appearances was in an episode of "I Love Lucy." Entitled "First Stop", air date January 17, 1955 Olin played the humorous role of a cafe and motel proprietor offering dubious accommodations to the road-weary Ricardos and Mertzes as they traveled by car en-route from New York to California. In 1958 and 1959, he was cast as Charley Perkins in five episodes of [[American Broadcasting Company|ABC]]'s [[sitcom]] ''[[The Real McCoys]]'', starring [[Walter Brennan]].
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