Pippo Popolino (Bob Hope), a humble tailor in Eighteenth century Genoa, impersonates the great lover and swordsman Casanova to try to woo lovely ladies like Francesca Bruni (Joan Fontaine) but is always found out. When the real Casanova flees town to escape his creditors he convinces Pippo to take his place. As a result a wealthy Genoan family mistake Pippo for the legendary lothario and task him to test the fidelity of intended bride Elena Di Gambetta (Audrey Dalton). Capitalizing on Pippo's predicament Francesca and scheming valet Lucio (Basil Rathbone) encourage him to pilfer Elena's petticoat as proof of seduction to collect their fee from the Gambetta family. To that end the unscrupulous pair try their utmost to transform hopeless schnook Pippo into a believable facsimile of the super-suave Casanova. Which proves no easy task.
Bob Hope was often at his best as an anachronistic comic presence in lavish period romps. So it is no surprise that Casanova's Big Night ranks among his funniest vehicles and is often singled out for praise by fans like Woody Allen (for what that's worth nowadays). Having previously directed The Paleface (1948) along with several notable comedy classics, Norman Z. McLeod was among a handful of directors that knew exactly how to tailor a movie around Hope's precise talents. Here he weaves a relatively sophisticated farce worthy of classical Italian comedy yet peppered with Hope's machine-gun patter and lovable fourth-wall breaking silliness. Along with showcasing Hope's trademark quickfire quips the script, co-written by Aubrey Wisberg, Edmund Hartmann and Hal Kanter, goes some way towards crafting a sympathetic tragicomic hero. A man whose amorous ambitions not only exceed his grasp but leave him humiliated at every turn by smug aristocrats. Including Vincent Price in a cameo as the honey-tongued serial seducer himself. The arc of the plot charts how Pippo's innate decency slowly eclipses his cowardice. His refusal to take advantage of Elena (an endearingly sweet turn by beautiful Audrey Dalton) sparks qualities he did not know he had that do not go unnoticed by Francesca.
Casanova's Big Night may not quite scale the same heights as Hope's previous period comedy, the thematically similar Monsieur Beaucaire (1946), but maintains a consistent hit rate of gags. Highlights include a musical scene where Hope serenades the swooning ladies of Venice by gondola like a cut-rate Bing Crosby, a slapstick sword-fight, his big dramatic soliloquy sharing a jail cell with a cackling Lon Chaney Jr. (which ends with a great punchline) and funniest of all: the costume ball with Bob and Joan in reverse drag, donning an ill-fitting ball gown and mustache respectively. Audiences at the time may have been surprised to see serious actors like Basil Rathbone (making his return to the screen after a five year absence) and especially Joan Fontaine in a Bob Hope comedy. Happily, far from slumming it, both enter into the spirit of the farce with great gusto. Fontaine in particular is a minor revelation exhibiting hitherto unseen comic talent. She upholds a longstanding tradition of Hope leading ladies cast as characters smarter, braver and more capable than ol' ski-nose's stock persona. Not only does Joan Fontaine handle most of the sword-fights and save Hope's life multiple times, she performs a hilarious mock-German accent. At a brisk eighty-six minutes Casanova's Big Night is a breezy, often delightful comic trifle that wisely does not outstay its welcome and climaxes with arguably one of the most memorable endings featured in any Bob Hope comedy.