Seven Sinners (1925)
One of three films Milestone directed with Marie Prevost, a former comedienne with Mack Sennett. Jack Warner appointed Darryl F. Zanuck as screenwriter.
A “semi-sophisticated” comedy incorporating elements of slapstick, Seven Sinners proved sufficiently successful with critics and the public to warrant Milestone, age 29, additional directing assignments.
The Caveman (1926)
Milestone delivered his second Prevost comedy The Caveman efficiently, earning praise for its “adroit direction.” During production, Milestone broke his contract with the studio over his exploitation as a “film doctor.”
Warners sued for damages and won, forcing Milestone to file for bankruptcy.
The Caveman would be his last film for Warners until Edge of Darkness in 1943. Undeterred, Milestone was quickly signed by Paramount Pictures.
The New Klondike (1926)
A sports-themed drama based on a Ring Lardner story was shot on location in Florida.
Despite “lukewarm” response from critics, Paramount was enthusiastic regarding Milestone’s prospects, showcasing him with other young studio talent in the promotional Fascinating Youth (1926).
A subsequent contretemps with screen star Gloria Swanson on the set of Fine Manners (1926) led to Milestone walking off the project.
Director Richard Rosson received credit when he completed the picture.
Two Arabian Knights (1927):
Considered Milestones most outstanding work during the silent era, Two Arabian Knights was inspired by the Anderson–Stallings stage play What Price Glory? (1924), and director Raoul Walsh’s 1924 screen adaption.
The first film in a four-year contract with Howard Hughes’ The Caddo Company—and his only film of 1927— it garnered Milestone an Academy Award for best comedy direction in 1927, prevailing over Charlie Chaplin’s The Circus (1927).
Set during World War I, doughboys William Boyd and Louis Wolheim, and their love-object Mary Astor form the triangle.
The Garden of Eden (1927)
Made under a Caddo releasing agreement with Universal Pictures, The Garden of Eden, a sophisticated variation on the Cinderella story, was adapted by screenwriter Hans Kraly.
It resembles, in both script and visual production, the works of Ernst Lubitsch.
The project benefited from the lavish sets designed by William Cameron Menzies and the cinematography of John Arnold.
The film stars the popular Corinne Griffith.
Milestone’s direction of Two Arabian Knights and The Garden of Eden established him as a practitioner of “rough and sophisticated” comedy.
The Racket (1928)
Wary of being stereotyped as a comedy director, Milestone shifted to an emerging genre popularized by director Josef von Sternberg in Underworld (1927).
The Racket, a taut and realistic depiction of mobster-controlled police department distinguished Milestone as an able practitioner of the genre, but its reception was damaged by the large number of superior gangster films released in the late 1920s.
The Racket was nominated for Best Picture at the 1928 Academy Awards.
