Aside from its name, Once Upon a Time in the Midlands borrows heavily from the classic spaghetti western Once Upon a Time in America. The music is there, as are some of the character elements. Yet everything takes place in a working class suburb in the English midlands. It doesn't seem like much of a fit, and most of the film struggles to figure out what it is about. It is at heart one of those quirky comedies from across the pond, populated with weird but likable characters. It is also an epic struggle for the heart of a woman, but the struggle is neither epic nor interesting. The film plods along its merry way, not caring that it has little plot, and that many of the characters are not interesting enough to sustain it. The love triangle revolves around Shirley (Shirley Henderson, Harry Potter and the Chamber of Secrets, 24 Hour Party People), a single mother. Shirley lives with her daughter Marlene (Finn Atkins, Better or Worse?) and her boyfriend Dek (Rhys Ifans, The Shipping News, Formula 51).

At the beginning of the film, Shirley is on one of those Jerry Springer/Ricki Lake type shows when Dek surprises her with a marriage offer. She tearfully refuses, and her old flame Jimmy (Robert Carlyle, Formula 51, The Beach), watching her on television, believes he may have a chance with her. He is a good-for-nothing cur, who abandoned Shirley and Marlene years ago. He is also the foster brother of Shirley's best friend Carol (Kathy Burke, The Martins, Love, Honour, & Obey) and her wacky husband Charlie (Ricky Tomlinson, Formula 51, Al's Lads), who wants to be a country singer.

Jimmy is a tough guy, and Dek is a wimp. Shirley loves both of them, but feels highly resentful of Jimmy's actions. Worse, Jimmy abetted in a robbery on his way there, so along with him comes a bunch of criminals looking for him. Director and writer Shane Meadows and co-writer Paul Fraser (A Room for Romeo Brass, TwentyFourSeven) have collaborated twice before, but here they're not really collaborating on anything. The main problem is that nobody cares who Shirley ends up with, including Shirley herself. Henderson's character waffles in a bored manner with her feelings between the two men. Everybody is just too simplistic. Jimmy is a jerk, with no obvious redeeming qualities. Dek is the obvious choice, but he is such a whiny wimp that people just want him to go away. Meadows and Fraser prolong the wait time between the inevitable confrontation between Dek and Jimmy, which itself is anticlimactic.