Originally conceived as a musical (called Asking for Trouble) to showcase the talents of leading lady Jessie Matthews, Climbing High emerged as a straight romantic comedy, albeit one that sometimes sets up musical numbers that don't occur. Michael Redgrave plays Nicky Brooke, a millionaire unhappily involved with a society dame who is primarily interested in him for his money and name. Matthews plays a beautiful young girl of limited means, Diana Castle, who works as a model (along with her roommate, Alastair Sim, portraying a communist forced to take a job as the loincloth-clad "before" picture in a muscle-building ad). While out driving, Brooke nearly runs over Diana; in the process, he falls for her but decides that he will have a better chance of getting his love returned if he courts her in disguise. Disguised as another ordinary working man, he succeeds -- until his real identity is revealed. More complications ensue -- including an escaped lunatic and a finale in which all of the characters end up climbing the Alps -- before Brooke and Diana end up together, where they always belonged.