In the Old West, a peaceful man named Tommy Stockburn (played by Adam Sandler), known to the Native Americans as "White Knife," is preparing to marry a Native girl named Smoking Fox (portrayed by Jennifer Jones). However, his life takes a turn when he encounters a gang of bandits, distinguished by their eye patches, led by the relentless Will Patch (voiced by Will Forte). With wit and bravery, Tommy cleverly outsmarts the gang, alongside a dangerously unstable food vendor named Clem (played by Jonny Zahn), who harbors a deep-seated prejudice against Native Americans and has a damaged left eye.
The plot thickens when a rugged bank robber named Frank Stockburn (depicted by Nick Nolte) arrives at Tommy's village, claiming to be his estranged father. Tommy learns that his mother was tragically killed by a mysterious figure adorned with a horseshoe tattoo during his childhood, a haunting memory that has troubled him for years. Furthermore, Frank reveals his imminent death from tuberculosis, while also hinting at a hidden stash of $50,000, buried near a pine tree, which he offers to help Tommy acquire.
However, things go awry when a group of bandits, led by the ruthless Cicero (portrayed by Danny Trejo), demands Frank's help to retrieve a past heist's "big score." Frank is forced to guide them to the said Singing Windmill at Jawbone Falls, promising to keep Tommy and the Natives safe in return. After a fruitless search for the buried money, Tommy resolves to seek another route to secure it and rescue his father.
Determined, Tommy embarks on a journey to raise the necessary funds through theft. Along the way, he discovers the existence of five half-brothers: Ramon (played by Rob Schneider), a Mexican burro rider; Lil' Pete (depicted by Taylor Lautner), who, despite his low intellect, has a strong neck and a cheerful demeanor; Herm (voiced by Danny Garcia), who communicates in a feral manner; Danny (played by Owen Wilson), a guilt-ridden drunkard with a surprisingly notable history; and Chico (portrayed by Terry Crews), a piano player who jokingly claims to be only half white. This motley crew joins Tommy on his quest.
In the midst of their adventures, Clem decides to ally with the bandits, seeking vengeance against Tommy for humiliating him. After Clem's gang captures Tommy’s fiancée, she manages to escape and sets out to find Frank. The brothers become embroiled with Smiley Harris (played by Harvey Keitel), a grinning saloon owner linked to Frank’s past, from whom they successfully steal a large golden nugget after a thrilling confrontation.
Their luck is soon tested again when Clem and the bandits invade their serene pond hideout. Though the brothers initially fend off the attackers, the gang manages to reclaim the stolen money from them. Nevertheless, hope shines bright when Herm, with Tommy's assistance, mentions an extravagant gambling event hosted by Ezekiel Grant (played by Jon Lovitz), featuring legendary figures like Mark Twain (voiced by David Spade) and General Custer.
After an adrenaline-fueled robbery of the poker game, Tommy's brothers acquire enough money to negotiate for Frank's release. However, an intense revelation occurs as Tommy discovers that it was indeed Cicero who took his mother’s life. Choosing to spare his brothers the danger, Tommy ventures out under the veil of night to rescue Frank and confront his mother’s murderer. Ransom paid, Cicero's plans to walk away peacefully are thwarted as Tommy stands firm on seeking revenge. A fierce showdown ensues, culminating in Tommy defeating Cicero, and his brothers join in a long-awaited reunion with their father.
The climax takes a turn when the $100,000 secured by their dangerous exploits is revealed to be a deceitful snare set by Frank, who conspires with Cicero. Yet, Tommy has a Plan B in place—a hidden bomb within the ransom bag! The dramatic explosion leads to chaos, with Frank fleeing with Smoking Fox deep into a mine while Tommy pursues them relentlessly. Ultimately, he rescues his fiancée, captures Frank, and uncovers the truth that the Left-Eye Gang had been fabricating their eye-patch requirement all along, inciting Clem's fury.
In the tranquil embrace of their Native village, Tommy finally weds Smoking Fox, with all his newfound brothers present. After the revelation of Frank's true nature as just another two-bit crook, the Native chief honors Tommy's half-brothers with adoption, solidifying their newfound family ties in the aftermath of chaos and heroism.
