A man nicknamed Stretch is thrown out of his car after a traffic accident in which the other driver, Candace, ignores a red light. Miraculously uninjured, he confronts Candace, only to fall instantly in love with her. A year later, Stretch is inspired to give up his addictions to cocaine and gambling. As Stretch considers proposing to her, Candace abruptly tells him that she wants to break up. Hurt by the sudden rejection, Stretch's life spirals into self-destruction and failure, which he blames on Candace. A failed actor, he works in Los Angeles as a limo driver. Though he has quit gambling, he retains a $6000 debt to Ignacio, who demands the debt be paid by midnight. At the same time, Stretch begins hallucinating the bitter ghost of another failed actor and limo driver named Karl, who committed suicide in front of a customer.
His boss, Naseem, calls him to his office and tells him that their chief competitor, a mysterious man known only as The Jovi, has been stealing their clients. Unless they can steal clients away from The Jovi, Naseem will be forced to fold his business. Although unsure how he will retain his job or pay back his debts, Stretch takes time to set up a blind date with a woman from an online dating site. At the same time, he begs Charlie, a sympathetic employee, to direct any high-paying customers his way. When The Jovi steals his first client, actor David Hasselhoff, Charlie sends Stretch to intercept one of The Jovi's clients, Ray Liotta. Liotta tasks Stretch with returning a pistol and prop badge, but before he can do so, Charlie sends him another client, Roger Karos, an eccentric playboy with a reputation for extremist hedonism. Karos parachutes down naked to the arranged location and offers to pay Stretch's gambling debt if he serves without question.
As Stretch drives Karos to exclusive nightclubs and hotspots of dubious legality, Karl berates him for putting himself at increasing risk, both personally and legally, for such a small sum of money. Karos' final destination is a secretive sex club. Karos gives Stretch 100 minutes to return to the sex club with an important briefcase and a supply of cocaine. When Stretch attempts to retrieve the briefcase, he learns from Laurent, a French blackmailer, that Karos has promised to trade a ledger for the contents of the briefcase. Using Liotta's props, Stretch successfully cons Laurent and his men into believing that he is a police officer, and they surrender the briefcase. As he leaves the nightclub, he sees Candace and nonchalantly insinuates that he is both successful and important now. When Candace expresses interest in him, he turns her down. Unimpressed, Karl continues to harangue him for his inadequacies.
Stretch procures the cocaine from a reality television star, who then steals the limo. Meanwhile, Liotta complains to Naseem, who fires Stretch. Undeterred, Stretch reacquires the limo, which has been trashed, only to lose it to The Jovi's brother, Boris, who operates a tow truck. Stretch once again retrieves the limo, though it has been reported as stolen. Stretch fast talks the security system operator into believing that he is a cop whose life is on the line during a gunfight, and he returns to Karos, who complains that he is a minute late. Ignacio also complains that he is late in his payment, and Stretch instructs Ignacio to meet him at Karos' destination. There, Karos abandons Stretch to The Jovi and Boris, though Ignacio intercedes. Laurent, revealed to be an American cop, also appears and arrests Karos, who is wanted for embezzlement. As Karos prepares to kill Laurent in a sneak attack, Stretch creates a diversion, saves Laurent's life, and escapes.
Later, at a diner, Stretch gives the ledger to Laurent, who declines to arrest him and compliments his acting skills. As Stretch looks around the diner, he realizes that he has ended up at the meeting point he set up with his blind date. He is surprised to find that the woman is there; when she is revealed to be Charlie, the two laugh and passionately kiss.Patrick Wilson as Stretch, a down on his luck limo driver and aspiring actor in debt to a Mexican gang.
Chris Pine as Karos, an eccentric billionaire wanted by the FBI. Pine went uncredited for the role.
Ed Helms as Karl, a successful limo driver who ultimately took his own life. He often appears as a hallucination to Stretch.
Jessica Alba as Charlie, a receptionist at Stretch's limo company and one of his few friends.
James Badge Dale as Laurent, an FBI agent attempting to capture Karos.
Brooklyn Decker as Candace, Stretch's ex-girlfriend.
Ben Bray as Ignacio, a bookmaker whom Stretch owes money to.
Randy Couture as the Jovi, a rival chauffeur.
Matt Willig as Boris, the Jovi's fearsome brother and a tow truck driver.
Shaun Toub as Nasseem, Stretch's boss.
Ray Liotta, David Hasselhoff, Norman Reedus, and Shaun White appear as themselves. Christopher Michael Holley plays Caesar, a door manager who has an altercation with Stretch. Jason Mantzoukas portrays Manny, a valet. Keith Jardine makes an appearance as a doorman.
Filming began in July 2013.
The film was originally set to be released on March 21, 2014. On January 21, 2014, the film's March release was scrapped by Universal Pictures, in what The Hollywood Reporter called "an apparently unprecedented move." The film's producer, Jason Blum, was unable to interest other distributors in the film, so it reverted to Universal Pictures. On September 25, the first official trailer was released. The film was released on iTunes and Amazon.com on October 7, 2014, before being released via VOD on October 14, 2014.
To coincide with the film's on-demand release, the filmmakers released a behind-the-scenes video showing the two leads Wilson and Decker going through the mechanics of filming a sex scene in the movie. This release received media attention.
Rotten Tomatoes, a review aggregator, reports that 83% of 12 surveyed critics gave the film a positive review; the average rating was 6.6/10. Jordan Hoffman of The Guardian wrote, "While the movie does eventually ramp up to a terrific purr, it hits plenty of speed bumps in its opening. There's a significant settling-in period (and some may just be unable to get on board at all), but it does settle in once the 'one night' begins." Ignatiy Vishnevetsky of The A.V. Club rated it B− and called it "puerile, demented, and often funny". Drew Taylor of Indiewire rated it B+ and called it a potential cult film if it can reach an adventurous audience. Cliff Wheatley of IGN rated it 8.9/10 and called it "a snowball of carnage and comedy". Scott Tobias of The Dissolve called it "an obnoxious cartoon version of Hollywood noir" that "confuses confidence and bravado for wit and fun".