Seventeen (1916)

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Booth Tarkington's novel was a current best-seller when this film adaptation was made. Jack Pickford -- younger brother of silent superstar Mary Pickford -- seemed to do well playing homespun characters (later on he appeared in Tom Sawyer and Bill Apperson's Boy), and he was a natural choice as the callow lead, 17-year-old William Sylvanus Baxter. Lola Pratt, William's "older woman" was another star from the Famous Players stable, Louise Huff, who was, in fact, a year older than Pickford, just like her character in the film. Madge Evans, who would grow up to become a pretty ingénue herself, played William's obnoxious kid sister. The film stays pretty close to the book -- William is desperate to impress Lola and spends all his money on her. He even steals his father's dress suit in an attempt to impress the young lady, who couldn't have cared less about him. Finally she promises to elope with him just so he'll leave her alone, and she runs off with an older man. Young William's first lesson in love is not a pleasant one. Seventeen was filmed again in 1940, with Jackie Cooper playing William.