Barrymore is Stephen Ashe, a highly skilled criminal defense attorney as well as an alcoholic. Both of these make him the Black Sheep of the old-money, very snobby Ashe family, along with his affectionate daughter Jan (Shearer). Jan is a free spirit (hence the title) who is reluctant to settle down with her pleasant but terminally bland suitor, Dwight Winthrop (Howard).
Instead she is drawn to Ace Wilfong (Gable), a local crime boss for whom Stephen just won an acquittal for murder. She spends the night with Ace, who instantly starts to grow possessive and controlling. Meanwhile, Stephen is aghast at his daughter's relationship with a criminal, so Jan offers him a deal: she'll quit Ace if he quits drinking.
A Free Soul won Barrymore the Academy Award for Best Actor. It was also a Star-Making Role for Gable (here billed fifth), catapulting him to leading man status, which he would retain for the rest of his career. This is Early Installment Weirdness for Gable, sort of, in that he's the villain, but the interesting thing is that this is only a minor tweak on the aggressively manly characters he'd play as a hero.
This film demonstrates the following tropes:
- Alcohol Hic: Stephen does this when showing up drunk for his mother's birthday party.
- The Alcoholic: Stephen is a hopeless drunk. His aides smuggle flasks into court. After he spends three months in the mountains drying out, he gets one bottle, and starts a bender that winds up with him sleeping on the streets with the other winos.
- All Girls Want Bad Boys: Jan is clearly bored by Dwight and lusts after Ace the criminal. After Dwight shoots Ace, she likes Dwight a lot better.
- Asian Speekee Engrish: Ace has an Asian servant with a stilted accent.
- As You Know...: Dwight is described as "one of the world's first dozen polo men."
- Betty and Veronica: A Gender Flip with Dwight and Ace. They're even color-coded correctly: Dwight is earnest, gentlemanly, adoring, very dull, and light-haired, while Ace is manly, charismatic, dominant, aggressive, and has black hair.
- Blackmail: Ace threatens that if Jan doesn't marry him, he'll tell everyone they had sex, and then no one will want to marry her.
- Damn, It Feels Good to Be a Gangster!: Ace is clearly enjoying himself, narrowly escaping a hail of bullets and treating the whole thing as a lark, and Jan does too.
- Entitled to Have You: After Jan sleeps with him, the formerly charming Ace suddenly becomes violently possessive, constantly saying that she's his and she has to marry him.
- Instant Death Bullet: Dwight shoots Ace, there is a very brief pause, and Ace keels over dead on his desk.
- The Oner: The second courtroom scene, in which Stephen cross-examines his daughter and then makes a passionate Oscar Bait speech, is a 14-minute take. This was done by using two cameras.
- Vehicle Vanish: A drunken, stumbling Stephen manages to do this with a train.