Kevin “Stretch” Brzyzowski, a failed actor turned limo driver in Los Angeles, drifts through life tethered to cocaine, alcohol, and gambling. Patrick Wilson anchors Stretch with a weary, jittery charm, giving the impression that luck is his only real skill. After a reckless car accident leaves him physically unscathed, he confronts the other driver, Candace, Brooklyn Decker and instantly falls in love. Over a year of dating, Stretch finds the nerve to ditch his addictions and propose, but Candace abruptly breaks up with him to be with a wealthy athlete. This heartbreak kicks off a self-destructive spiral: he stays sober in body, yet carries a $6,000 gambling debt to the Mexican mafia, and begins hearing the bitter ghost of Karl, a failed actor and limo driver who killed himself before two customers. Karl is portrayed by Ed Helms and surfaces in unsettling, hallucinatory conversations that blur the line between memory and madness.
Stretch’s boss, Naseem, Shaun Toub, warns him that their chief competitor, a mysterious man known only as The Jovi, Randy Couture has been stealing their clients. Unless Stretch can steal clients from The Jovi, Naseem will be forced to fold the business. The mafia also demands that Stretch resolve his debt by midnight. Stretch begs Charlie, Jessica Alba, a sympathetic coworker, to direct any high-paying customers his way, since a generous tip is his only hope for paying in time. Although unsure how he will solve his problems, Stretch sets up a blind date with a woman online, hoping romance might offer a temporary reprieve from the escalating pressure.
When The Jovi steals Stretch’s first client, the iconic actor David Hasselhoff, David Hasselhoff makes a fleeting appearance in this chaotic ride. Charlie then sends Stretch to intercept one of The Jovi’s clients: Ray Liotta, Ray Liotta, a menacing presence who is filming a project at the studio. Liotta tasks Stretch with returning a prop pistol and badge to the production lot, but before Stretch can complete the simple task, Charlie pushes him toward another high-ticket client: Roger Karos, Chris Pine, an eccentric and hedonistic millionaire who promises to pay Stretch’s debt if he serves him for the night, no questions asked. Karos orders to be dropped off at a secretive sex club and gives Stretch 99 minutes to see a certain man across town, then return with an important briefcase and a supply of cocaine. Stretch’s mission becomes a high-stakes scavenger hunt across the city, filled with dazzling surfaces and dangerous loyalties.
Stretch’s path leads him to Laurent, James Badge Dale, a French criminal who is promised some mysterious ledgers in exchange for the contents of the briefcase. Knowing nothing of the ledgers, Stretch improvises a plan: he uses Liotta’s prop gun and badge to impersonate a police officer, and Laurent’s gang surrenders the briefcase. As he leaves the nightclub, he sees Candace again and revels in the illusion that he has become somebody important, briefly pleased by the attention.
Back at Naseem’s operations, trouble erupts as the mafia complains about missing props and the limo’s operating system is shut down via remote access. Boris, Matthew Willig, The Jovi’s brother who operates a tow truck, arrives to tow the limo away. Stretch murders time with a risky bluff, persuading the security-system operator that his life is on the line in a gunfight, restoring the car’s status and escaping. He then secures Karos’s requested cocaine from a reality-television star, who ends up stealing the limo, only for Stretch to reclaim it—and Boris to close in again. A tense highway pursuit follows as Stretch dials chaos into a daring escape, detaching the limo from the tow truck to outrun the threat.
Karos growls that Stretch is one minute late with the debt payment, and the Mexican mafia presses for results as the night wears on. Karos coldly abandons Stretch to The Jovi, Boris, and the mafia, revealing that he never planned to tip him the $6,000. Laurent arrives to arrest Karos, and when Karos makes a lethal move on Laurent, Stretch creates a diversion, saves Laurent’s life, and slips away into the morning light.
The next morning, Stretch delivers the ledgers to Laurent, who declines to arrest him and complements Stretch’s acting, acknowledging that tonight’s caper was a performance of risk and improvisation. At the diner where he arranged the blind date, Stretch scans the room and finally discovers that his date is Charlie. The moment of recognition gives way to laughter and a kiss, signaling a fragile but hopeful new chapter for both of them as they face an uncertain future together.
