When You're Smiling is distinguished by the presence of several top recording artists of 1950. The wafer-thin plotline concerns the misadventures of Texan Gerald Durham (Jerome Courtland), who arrives in the Big City to learn the ropes of the music business. Durham not only ends up with a recording contract, but also wins heroine Peggy Martin (Lola Albright) in the bargain. So much for the story. The principal selling card of When You're Smiling consists of the guest-star turns by Frankie Laine, Bob Crosby, The Modernaires, The Mills Brothers, Kay Starr and Billy Daniels.
Andy Clark discovers he was cheated out of a half interest in partner Mike's business, now a thriving dance hall in 1892 Chicago. Unable to win it back, Andy schemes to make Mike's position untenable. He also hopes to turn Ruby Summers, Mike's motor-mouthed burlesque queen, into a classier entertainer, and incidentally to make her his own. But at the last minute, Andy's revenge comes unravelled.
Nancy Evans, lovely circus owner, has a ranch that she's never visited, but for sentimental reasons won't sell to Mike Abbott. Her partners, secretly in league with Abbott, sabotage the circus to force Nancy to sell the ranch; instead, she goes there to live. Will her neighbors, the Three Mesquiteers, be a match for the secret swindlers? And what's so valuable about that run-down ranch anyway?