Gilbert Gilbert is one of three half-brothers — Buster Da Costa and Pooch Donahue — sons of their debt-ridden, chronically remarried mother, Mrs. Smythe Mrs. Smythe. As the furniture is hauled away by the broker’s men, he breaks into a song he’s written himself, Takes Two to Make a Bargain, a playful number that pokes fun at misfortune with lines like “Did you ever see a piano walking?” and the cheeky reminder that “Pianni doesn’t live here anymore.” The moment captures Gilbert’s wild blend of charm and desperation, setting the tone for a comic tale about art, luck, and the hit-or-miss path to show business success.
Desperate to sell the tune, Gilbert corners Alexander Myers Alexander Myers, a song publisher who is, unknown to Gilbert, completely deaf. The meeting is interrupted in a farcical twist when a plane circles overhead and crashes into the tree where Gilbert is hiding. The accident leaves him injured, and soon his family learns that his mother has sued the pilot for 50,000 dollars, arguing that the crash prevented Gilbert from finishing his musical play. Gilbert is shocked to discover the money dispute is not about a finished work but about compensation, and he protests that he never even had a finished play to begin with. The tangled situation lands him in a new kind of trouble when he encounters the pilot, Bobbie Bobbie, who offers to cover the debt in installments of 15 dollars a week from her salary as secretary to the theatrical producer Harry Kling.
Bobbie arranges a meeting for Gilbert with Kling, who is grappling with finding a suitable vehicle for his actress girlfriend Lilly Lilly. Gilbert attempts to explain the accident to Kling, but the producer takes it as a pitch for a play and orders him to have something ready by the time Kling returns from Paris in seven days. With a pool of actors at Kling’s Long Island estate, Gilbert envisions a new musical called Two for Tonight, and the workshop begins in earnest. He performs for Bobbie, singing From the Top of Your Head, hoping to spark the right inspiration, while Homps Homps, the estate’s shrewd butler and a former Budapest producer, weighs in with practical advice and a hint of hustling from the old theater world.
As the sessions unfold, Bobbie tries to push Gilbert toward romance to generate material, but Lilly keeps stepping in, and a showbiz triangle forms around the music, the dates, and the pressure to deliver. After a quarrel and a misstep, Gilbert accidentally trips a waiter and triggers a mêlée at the Purple Cafe, which escalates into a riot that draws in the police and even lands Gilbert in jail. Bobbie visits him behind bars, and he serenades her with I Wish I Were Aladdin as a chorus of prisoners joins in the performance.
When he’s released, the rehearsal continues, but a romantic misunderstanding between Bobbie and Lilly disrupts proceedings and Kling’s patience thins. The producer declares the project dead, and there’s a tense pause until Homps reveals that his Uncle Ludwig has died and left him the funds to finance the production. With that news, Gilbert renews his pursuit of Bobbie, declaring his devotion, and, after he again performs Without a Word of Warning, she returns to him for a hopeful ending. In the final scene, Homps and Mrs. Smythe appear arm-in-arm, and Mrs. Smythe seems poised for yet another marriage as the curtain falls on a comic, hopeful note.
