Two convicts, the clever yet charismatic Joe (played by Bruce Willis) and the neurotic hypochondriac Terry (portrayed by Billy Bob Thornton), pull off a daring escape from Oregon State Penitentiary using a concrete mixer. With big dreams of funding their fantasy life, they embark on a spree of bank robberies. Their adventure begins when Joe cleverly realizes the prison's main gate takes a while to operate, allowing their escape in a commandeered concrete truck. Although Terry, concerned for Joe’s safety, jumps on board, Joe takes the lead with his raw strength while Terry provides the brains behind their daring heists.
Almost immediately after their breakout, Joe steals a woman's car to drive them to their first bank, ready to use a magic marker as a mock weapon against the lone security guard. Joe's weakness for attractive women soon complicates their criminal endeavors. Upon successfully robbing the bank, the duo makes a quick getaway, finding refuge in a garage belonging to Cheri Woods (Azura Skye), whose family they unintentionally ensnare. In Cheri's house, the friends concoct a plan to fulfill their dreams of opening a resort in Acapulco while donning the attire of Cheri's father to blend in seamlessly.
Terry articulates the challenges of robbing banks, emphasizing the unpredictability of alarms and people. He devises an ingenious method to take control of the situation. They earn the moniker "Sleepover Bandits" for their unusual technique of kidnapping bank managers the night prior to heists, spending the night with their families, and calmly accompanying them to the bank the next morning. They engage Joe's dim-witted cousin Harvey Pollard (Troy Garity) as their getaway driver; Harvey dreams of making a name for himself as a special effects artist, which adds another layer to their criminal misadventures.
Their first target is Oregon City Bank, where they manage to abduct the family of bank manager Darill Miller (Brían F. O'Byrne), ensuring their elaborate heist runs flawlessly. They become well-known, catching the attention of the FBI, who list them among America's Most Wanted, with a reward for their capture eventually reaching $1 million.
Amid the chaos, a woman named Kate (Cate Blanchett), seeking an escape from her crumbling marriage, crosses paths with Terry during a desperate moment. Stranded on a bridge, Terry is rescued by Kate, who is in her own turmoil. As she insists on driving him to his destination, Terry unwittingly introduces her into their hideout, where Joe, originally furious, is soon charmed by Kate's presence. Their bond begins to blossom, particularly over shared literary interests, leading Kate to participate in their heists.
However, the plot thickens when a tragic car accident, which occurs while Harvey is at the wheel, leaves Joe and Terry on edge as they navigate a confusing love triangle with Kate. After a string of successful robberies, their criminal rollercoaster ride spirals into tension-filled disagreements over Kate, leading her to ultimately break away from both men.
The story unfolds in a series of flashbacks narrated by the fictional reality show Criminals at Large, which recounts the duo's last fateful robbery at Alamo Bank. The climax is a dramatic twist involving betrayal, as Kate tips off the police during their final heist. Tensions boil over, resulting in an explosive confrontation where Joe defiantly declares, >“You won’t take us alive!"
In an unexpected turn, rather than the violent end they anticipated, it is revealed that Harvey used special effects to stage their demise, leading the authorities to believe Joe and Terry perished in the chaos. Escaping in the mayhem, the crew, consisting of Joe, Terry, Harvey, and Kate, ultimately find refuge in Mexico, embracing the life they dreamed of. The final scenes depict Harvey marrying in Mexico, with Kate sharing passionate moments with both Joe and Terry, leaving the audience with a bittersweet ending for their twisted adventure.
