Calamity Jane (Doris Day) is the tom-cowboy to end all tom-cowboys, known for her feisty attitude and tallish tales of fighting Indians. When saloon/theater owner Henry Miller (Paul Harvey) is faced with angry Deadwood residents because he tries to pass off a man in drag as the attractive New York actress he promised (he made the mistake based on the actor's name), "Calam" promises to go to "Chicagee" and bring back an actress all of the men are going gaga for because of her picture on cigarette cards.
Director David Butler's Calamity Jane delivers on many ends--it's a musical featuring catchy songs, many sung by one of the greatest songstresses of her era, Doris Day, and a few incredibly choreographed; it's a frequently hilarious comedy; it's suspenseful in quite a few scenes (usually through realistic dramatic tension); it's a beautifully shot western with fantastic sets; and in the end, it's a grand romance.
Day carries the film with her unusual, enjoyable, amusingly butch character. She plays Calamity Jane with boundless energy and physical aplomb--you wouldn't catch many modern film performers doing some of the stunts that Day does here. Butler usually keeps the camera close enough to Day that you can see it's her--she hasn't been supplanted with a stuntperson, and during one bit of choreography, Butler has Day jumping and flipping over bars and being taken up to a second story balcony and set back down with lots of uninterrupted takes. Most modern directors would break up the choreography into a series of relatively easy steps, creating physics defying agility through clever cutting. Day has to perform the steps as if she were doing the number on a Broadway stage.
Calamity and most of the rest of Deadwood, South Dakota are funny because of their backwoods naivety. That can be a difficult thing to sell to viewers, but when Francis Fryer (Dick Wesson) almost gets away with his necessary cross-dressing shtick, it's believable. Calamity's trip to Chicago has some particularly hilarious moments. The humor also works as well as it does because the two men who are the later romantic interests, Wild Bill Hickok (Howard Keel) and Lieutenant Danny Gilmartin (Philip Carey), are the primary ones who seem to have a more objective perspective on the town's gullibility and Calamity's tall tales (although there are hints that their skepticism is not so uncommon).
Many viewers are most attracted to the film because of its evolution into a romance in the last act. Day's transformation in this section is handled expertly--if you watch her closely, she never quite loses her Calamity tomboyishness, but she also makes more than just a physical transformation. But it's not just Day who is excellent--all of the performances in the film are good.
For me, Calamity Jane is one of the most successful combinations of comedy and a still serious western. It's everything that Cat Ballou (1965) should have been, but mostly fell flat with. Don't miss it if you're a fan of either musicals or good-natured westerns.