Tired of his "white Pants Willie" roles and depressed after the deaths of his father Belmont and sister Kay, he had to pay off the family debts and prepare vigorously his next Hollywood assault.
His breakout happened in The Petrified Forest (1936), thanks to Leslie Howard's insistence. His performance was described as "superb", and his effort playing the criminal Duke Mantee as sheer "class" by The Hollywood Reporter. In 1937 (the year he divorces Mary Philips) he plays gangster Baby Face Martin in Dead End directed by William Wyler. His alley scene with Claire Trevor (nominated to Best Supporting actress) oozes despair, framed by Toland's gritty cinematography.
In 1938 Bogart married Mayo Methot (The Portland Rosebud actress in the The Mad Honeymoon play by William Brady) with whom he worked in Marked Woman. The relationship with Mayo would mark the lowest point in Bogart's emotional stability, since "Sluggy" (he also called her Madam) behaved in paranoid and aggressive mood, even stabbing Bogart once.
Bogart played another outlaw in High Sierra directed by Raoul Walsh in 1941. According to Walsh, on the set of They Drive by Night: "the salary was his only thrill." His role as Roy Earle in High Sierra was called "the twilight of the American gangster" by The New York Times. "I wouldn't give you two cents for a dame without a temper," Bogart says to Ida Lupino. Irving Rapper (High Sierra's dialogue director) remembers Bogie infatuated with Ida.
However, he could be shy shooting kiss scenes: in The Maltese Falcon by Huston (1941), Bogart needed to repeat 7 takes. Mary Astor, who played the femme fatale betrayed by Sam Spade, explained that Bogart had a saliva trouble.
His final lowlife gangster role was in The Big Shot in 1942. The same year he played Rick Blaine in the most romantic film ever: Casablanca directed by Michael Curtiz, Ingrid Bergman playing Ilsa Lund (inspired by the angelic Ilse from "Harz Journey" poem by Heine) which would catapult Bogie as a true movie star (even a sex-symbol) leaving behind his contract player status in Warner. Huston said Bogie wasn't a womanizer.
The next movie for Bogart that transformed him into a definitive legend was The Big Sleep (1946) by Howard Hawks, after To Have and Have Not (1944) the film based on a Hemingway's novel that featured Lauren Bacall's entrance into Bogart's romantic awakening.
Raymond Chandler, author of The Big Sleep novel, although he wouldn't help Hawks much about his famously complicated story plot, he praised Bogart's interpretation of Phillip Marlowe: "Bogart can be tough without a gun. Also, he has a sense of humor that contains that grating undertone of contempt".