The viewer is readily suckered into the impression that this is a Hilary Swank movie showcase. She plays strong frontierswoman Mary Bee Cuddy, a tough cookie who can match any man, but who knows she is aging and secretly yearns for a husband and family. Her desperate proposal to a would-be candidate is roundly rejected, despite her relative wealth, since she is plain as the proverbial pikestaff. She believably rounds out the role.
When three local women lose their marbles for various reasons, leaving their families unable to cope, Mary Bee 'wins' the draw to drive them back east to Iowa, across the Missouri, where they can receive the necessary care. She seems every bit as competent -- if not more so -- than the weak-willed men who should have undertaken this five-week traipse across the prairie. However she realises that a man's help could be useful, and she enlists the services of wastrel and general chancer Tommy Lee Jones, who has been left to hang by vengeful locals -- not that they actually hanged him, but left him sitting on his restless horse with one end of the rope attached to the tree above. Mary Bee agrees to cut him loose and to pay him 300 dollars at the end of the trek if he in turn swears to help her look after her three crazy charges.
The madwomen are played by Grace Gummer, Miranda Otto, and Sonja Richter and prove more than a handful for their mismatched minders. Swank and Jones gradually develop a modus operandi and a grudging respect for each other, despite his history of running away from any challenge when the going got tough (the army, a marriage) and her revealing her buried softer side. (Incidentally, he too dismisses a tentative marriage proposal). Then two-thirds through the film Swank's Mary Bee is unexpectedly and shockingly written out of the script and it becomes, what it was probably intended to be all along, a starring showcase for Tommy Lee, who directed the movie (his second directorial outing) and who co-wrote and co-produced. His usual curmudgeonly character is given top billing in a movie that Clint Eastwood would have been proud of, less a classic Western, more a character-driven road movie through the early pioneering days.
With Mary Bee out of the frame and having found the promised $300, Tommy Lee's first thought is to abandon his mad charges, but they chase after him and he perseveres through many hardships to get them back 'east'. Chuffed by his unexpected success and gradually accepting what a fine woman Mary Bee was, the viewer fully expects him to emerge as a reformed character. However, contrary to all expectations, he regresses -- sadly in this case -- to the feckless ne'er do well he has always been. What has been an occasionally humorous journey reveals itself to be an actual tragedy in the end moments.
One shouldn't have too many high expectations at seeing Meryl Streep's name in the 'and' role in the front credits. Hers is a brief cameo as the holier-than-thou Reverend's wife with whom the three mad ladies are deposited (a role than any middle-aged actress could have played, but no doubt agree to because of the casting of her daughter Gummer). In fact the movie is full of second-rank well-known actors: Barry Corbin, David Dencik, William Fichtner, John Lithgow, Tim Blake Nelson, James Spader, and Hailee Steinfeld., who each have a few minutes to strut the stage. The truth is that this is the Swank-Jones Show with the final emphasis very much on Jones.