Writer Skip Donahue (Gene Wilder) and ambitious actor Harry Monroe (Richard Pryor) find themselves unexpectedly out of work after being fired from their jobs in New York City. In search of a fresh start, the duo heads to Hollywood with dreams of making a living in the entertainment industry. However, as they travel through various stops, they’re forced to take on a string of odd jobs just to keep their heads above water. In a particularly bizarre turn of events, they end up donning the costumes of two woodpeckers, performing a catchy song and dance routine to promote a local bank.
As their luck would have it, during a much-needed break from their performance, they unwittingly lose their costumes to two opportunistic thieves who decide to impersonate them. The thieves proceed to use the outfits to rob the bank, leading to a chaotic sequence of events that results in Skip and Harry’s immediate arrest. The duo soon finds themselves thrust into an absurdly rapid trial, where they are handed a staggering sentence of 125 years in prison in the blink of an eye. Their court-appointed attorney, Len Garber (Joel Brooks), advises them to stay put until he can appeal their case, which promises to be quite the ordeal.
Life inside the walls of a maximum-security prison proves to be as comical as it is difficult for both Skip and Harry. As their attempts to feign insanity fall flat, they begin to navigate the complexities of prison life, befriending Jesus Ramirez (Miguel Ángel Suárez), a seasoned bank robber, and Rory Schultebrand (Georg Stanford Brown), a flamboyant inmate with a murky past. This friendship becomes crucial as Rory develops a certain fondness for Harry, leading to some amusingly awkward moments for Harry himself. As days turn into weeks, the two new friends are educated about the inner workings of the prison, all while keeping an eye out for dangerous inmates like Jack Graham (Jonathan Banks), the ruthless block captain, and the ferocious Grossberger (Erland Van Lidth), a giant mass murderer who’s struck fear into the hearts of both inmates and guards with his imposing presence.
With three months behind bars, the duo is called in to meet the warden, Walter Beatty (Barry Corbin), and his deputy, Wilson (Craig T. Nelson). Unbeknownst to them, a mechanical bull is about to become a pivotal element of their fate. To everyone's astonishment, Skip rides the bull with remarkable skill, earning himself a spot in the prison's notorious rodeo competition—a known ruse that benefits only the corrupt prison officials. As Jesus and Rory inform Skip and Harry about the grim realities of the rodeo, revealing it as a scheming operation that fills the wardens' pockets instead of benefiting the inmates, they concoct an elaborate plan to escape. For this to work, Skip must first refuse to join the rodeo festivities, which brings the wrath of the warden down upon both him and Harry.
As tension in prison escalates, the guards implement increasingly harsh punishments to break the spirits of Skip and Harry. This ranges from grueling labor to sleep deprivation, and eventually leads to Skip being locked up in solitary confinement. The result of this severe treatment is surprisingly beneficial, as it remarkably alleviates Skip's chronic back pain. During their incarceration, the duo has their lives twisted further by the whims of the corrupt prison guards, including an unexpected friendship with Grossberger, who turns out to be more complex than initially perceived.
Their hope to prove their innocence begins to flourish when Garber and Meredith (JoBeth Williams), Garber's cousin who is also invested in their case, visit them. Skip finds himself quite charmed by Meredith, whose determination fuels a new spirit for escape among the inmates. Meanwhile, the simmering tensions between the guards and the inmates continue as Warden Beatty, furious at Deputy Wilson's failure to break Harry and Skip, steps in personally to escalate matters.
As the rodeo approaches, the truth about the operation comes to light. As they prepare for competition, Skip and Harry, along with their unconventional team, begin to forge tools that will aid in their much-anticipated escape. In the meantime, outside of the prison walls, Meredith, working undercover at a country western establishment, uncovers crucial information about the real criminals behind the bank heist and contacts Garber for assistance.
When the rodeo finally kicks off, the stakes are higher than ever as Skip and his crew must juggle their performance while executing their escape plan. Accusations fly, and in a stunning twist, Caesar Geronimo (Joe Massengale), the current champion, comes to a moment of reflection inspired by Skip's words, which leads him to share the prize money—much to the shock of the authorities.
In a climactic escape sequence full of daring maneuvers and close calls, Skip, Harry, and their friends successfully manage to evade capture and reach a safe location, only to find themselves met by Meredith and Garber. With newfound hope and vindication at their fingertips, they learn that Meredith's hard work has finally yielded results: the actual culprits have been apprehended, leading to the clearing of Skip and Harry's names. Overjoyed by this turn of events, Skip seizes the opportunity to invite Meredith on their new adventure as they set their sights back on Hollywood, dreaming once again of brighter horizons.
