structural:scholar_edition, linguistic:translation, structural:reformatting, linguistic:paraphrasing
First performances

Bogart returned home to find his father in poor health, his medical practice faltering, and much of the family's wealth lost in bad timber investments. His character and values developed separately from his family during his navy days, and he began to rebel. Bogart became a liberal who disliked pretension, phonies and snobs, sometimes defying conventional behavior and authority; he was also well-mannered, articulate, punctual, self-effacing and standoffish. After his naval service, he worked as a shipper and a bond salesman, joining the Coast Guard Reserve.

Frank Kelly Rich writes that Bogart "dove headfirst into the Jazz Age lifestyle, always up for late night revels... When his meager wages were exhausted, he'd play chess against all comers in arcades for a dollar a match (he was a brilliant player) to fund his outings." Mike Doyle of Chess.com writes that "Before he made any money from acting, he would hustle players for dimes and quarters, playing in New York parks and at Coney Island." Bogart resumed his friendship with Bill Brady Jr. (whose father had show-business connections), and obtained an office job with William A. Brady 's new World Films company. Although he wanted to try his hand at screenwriting, directing, and production, he excelled at none. Bogart was stage manager for Brady's daughter Alice 's play A Ruined Lady. He made his stage debut a few months later as a Japanese butler in Alice's 1921 play Drifting (nervously delivering one line of dialogue), and appeared in several of her subsequent plays.

Although Bogart had been raised to believe that acting was a lowly profession, he liked the late hours actors kept and the attention they received: "I was born to be indolent and this was the softest of rackets." He spent much of his free time in speakeasies, drinking heavily. A bar-room brawl at this time was also a purported cause of Bogart's lip damage, dovetailing with Louise Brooks' account.

Preferring to learn by doing, he never took acting lessons. Bogart was persistent and worked steadily at his craft, appearing in at least 18 Broadway productions between 1922 and 1935, 11 of which were comedies. He played juveniles or romantic supporting roles in drawing-room comedies and is reportedly the first actor to say, " Tennis, anyone? " on stage. According to Alexander Woollcott, Bogart "is what is usually and mercifully described as inadequate." Other critics were kinder. Heywood Broun, reviewing Nerves, wrote: "Humphrey Bogart gives the most effective performance... both dry and fresh, if that be possible". He played a juvenile lead (reporter Gregory Brown) in Lynn Starling 's comedy Meet the Wife, which had a successful 232-performance run at the Klaw Theatre from November 1923 through July 1924. Bogart disliked his trivial, effeminate early-career parts, calling them "White Pants Willie" roles.

While playing a double role in Drifting at the Playhouse Theatre in 1922, he met actress Helen Menken; they were married on May 20, 1926, at the Gramercy Park Hotel in New York City. Divorced on November 18, 1927, they remained friends. Menken said in her divorce filing that Bogart valued his career more than marriage, citing neglect and abuse. He married actress Mary Philips on April 3, 1928, at her mother's apartment in Hartford, Connecticut; Bogart and Philips had worked together in the play Nerves during its brief run at the Comedy Theatre in 1924.

Theatrical production dropped off sharply after the Wall Street Crash of 1929, and many of the more-photogenic actors headed for Hollywood. Bogart debuted on film with Helen Hayes in the 1928 two-reeler The Dancing Town, which survives intact. He also appeared with Joan Blondell and Ruth Etting in a Vitaphone short, Broadway's Like That (1930), which was rediscovered in 1963.