Take It Big (1944)

Jack Haley plays Jack North, the nether end of a vaudeville horse act who inherits a western ranch. When he heads to the Great Outdoors to take possession, Jack winds up at the wrong place: a swanky dude ranch. He immediately begins running things, at it's quite a while before his error is discovered. By the time he shows up at his own ranch, he's up to his ears in unpaid debts-which naturally requires a fund-raising musical show as a bail-out. Harriet Hilliard handles the romantic portion of the proceedings, occasionally dueting with her real-life husband, bandleader Ozzie Nelson.