Hepburn plays the title role of Sylvia Scarlett, a female con artist masquerading as a boy to escape the police.

In the U.S., by sixteen, he began to attempt to sound more American to broaden the range of theatre roles for which he could be cast a decade before he ever appeared in a Hollywood "talkie".

Henry wants to escape on his own and not arouse suspicion by traveling with a young girl, so Sylvia insists that she go along and decides to pose as a boy for safety and practicality.

On the channel ferry to London, they meet a "gentleman adventurer," Jimmy Monkley and Henry soon explains his smuggling plan over drinks.

Posing as a traveling troupe of entertainers, they perform for a rowdy local crowd but one of the hecklers, a roguish artist named Michael Fane, catches the interest of Sylvia who decides to reveal her true identity.

After a disastrous test screening, Cukor and Hepburn reportedly begged producer Pandro Berman to shelve the picture if they agreed to make their next film for free.

According to RKO records, the film lost a whopping $363,000,[1] and thus began a downturn in Hepburn's career (causing her to be branded "box office poison") from which she would eventually recover.

[2] In a review published two days before his death, Andre Sennwald of the New York Times wrote "With what accuracy Compton Mackenzie's novel has been transferred to the screen this deponent knoweth not.

"[5] John Mosher of The New Yorker was positive and found that despite Hepburn's difficult role, the picture was "charming, sparkling with the feeling that Compton Mackenzie gave his novel of romantic vagrants.

"[11] It is considered that the sexual ambiguities and gender misunderstandings of the films were too daring for the time period, which made the audiences fail to see the humor in cross-dressing and mistaken identity.

[13] Some have argued that "Gender as a separate concept from sexuality or physical sex wouldn’t come about for another twenty years, so audiences had no context for Sylvia’s odd apparel" throughout the movie.

[15] It is now seen as "a monument to the sapphic impression Hepburn left in Hollywood",[16] with the film implying "that Sylvia might stay as Sylvester forever," even as she enters a relationship with a man.