Monty Westmore was the youngest of six sons in a family of makeup artists. George Westmore, Monty's father, founded the first makeup department at a major motion picture studio. Westmore's mastery of makeup techniques quickly garnered attention in Hollywood. Under George's guidance, the family established a makeup dynasty in Hollywood that lasted four generations.
Monty Westmore was the first to leave home when he began working as a busboy at Famous Players-Lasky studio during the 1921 shooting of The Sheik. There, he met Rudolf Valentino, who had been doing his own makeup during filming. Westmore—after demonstrating his skills to the studio bosses—became Valentino's primary makeup artist until the actor's death in 1926. By this time, Westmore had begun freelancing. His work on Mutiny on the Bounty caught the attention of David O. Selznick, and he was hired as head of the makeup department at Selznick International Pictures.
Like all the designers on Gone With The Wind, Westmore did intensive research long before filming began. The task he faced was daunting. Many scenes of the film had scores of extras who needed makeup. The major characters needed to simultaneously look like stars and look natural. Through several months of filming, dozens of major characters needed to appear to age significantly. At times, as many as three scenes were shot simultaneously with the star characters.
Westmore also had to accommodate the new Technicolor process, which was so sensitive it could pick up the color of an actor's costume reflected in another actor's face. Cooperating with Walter Plunkett, the costume designer, and Ernest Haller, the cinematographer, Westmore managed to keep Vivien Leigh's naturally blue eyes looking green.
Westmore personally applied the makeup for all the Scarlett O'Hara screen tests. He met Selznick's high demands while simultaneously working on the films Rebecca and Intermezzo. Westmore suffered a heart attack and died less than a year after Gone With The Wind was released. Because makeup artists did not regularly receive screen credit for their work until the 1940s, Westmore's substantial contributions to the success of Gone With The Wind were not publicly acknowledged in his lifetime.