In the wake of a turbulent history, Jimmy "The Saint" Tosnia (played by Andy Garcia) strives to escape his former life as an notorious gangster. Now running Afterlife Advice in Denver, he helps the dying leave touching messages for their loved ones. However, his efforts are in vain as the business struggles to stay afloat, attracting the unwanted attention of his former boss, the merciless crime lord known as The Man With The Plan (Christopher Walken). This malevolent figure, rendered a quadriplegic from a tragic accident, exploits Jimmy's financial problems to force him into a grim favor: to convince Meg, the ex-girlfriend of his incarcerated son Bernard, to rekindle their romance, believing it will somehow save Bernard from his heinous off-the-wall charges of child molestation.
Cornered and desperate, Jimmy assembles a ragtag team of former associates, including Easy Wind, Pieces, Big Bear Franchise, and the unpredictable Critical Bill. Their ludicrous scheme involves masquerading as law enforcement to intimidate Meg's current partner, Bruce, into breaking up with her. However, chaos ensues when Bruce grows suspicious, throwing their plan into disarray and leading to horrific consequences—the violent confrontation leads to Meg's accidental death, spurring ire from The Man With The Plan.
For their failure, Jimmy receives a dubious clemency—banished from Denver for life—while his former friends suffer a more harrowing fate, promised to die a brutal death known as "buckwheats." The relentless hitman Mr. Shhh becomes their executioner, and as pieces fall into place, Pieces comes to terms with his fate when Mr. Shhh swiftly delivers his end.
In a bid for survival, Easy Wind seeks shelter with Baby Sinister, a powerful gang leader, but their refuge is swiftly compromised as Mr. Shhh decimates Sinister's men. Franchise, desperate to protect his own family, pleads with The Man With The Plan for mercy, but his efforts are futile—Franchise is cruelly betrayed and killed.
As the cycle of violence spirals out of control, Jimmy is confronted with the grim reality of his own fate and must contend with the fact that he may soon meet the same savage demise as his friends. The hunt intensifies as Mr. Shhh closes in on Critical Bill, leading to a violent clash that claims both of their lives. Following this, the contract on Jimmy's head shifts to a trio of merciless Mexican brothers determined to end him. With the specter of death looming, Jimmy takes a heartfelt moment to bid farewell to Dagney, the young woman whose love has intertwined with his own, and seeks vengeance upon Bernard.
In an unexpected turn of redemption, Jimmy also helps fulfill the wishes of Lucinda, a hopeful mother desiring a child, as he leaves behind a poignant video message for his unborn offspring. As the trio of killers converge, Jimmy encounters his end with calm acceptance, reuniting his spirit with those who have gone before him. The Man With The Plan mourns the loss of his son, while Jimmy finds solace in the afterlife, joyfully gathering with his friends and raising "boat drinks" to eternal memories together.
