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  • Box Office Bomb: Budget, $37 million. Box office, $44,875,481 (domestic), $55,439,786 (worldwide).
  • Creator Backlash: While he always claims to have a soft spot for his less successful films, Kevin Smith has said that this is the only movie he completely hated making. Because of this film, he finally got fed up with having to work within Hollywood's rules and returned to the indie scene with Red State.
    • Smith also regrets his comments against Willis in the aftermath of this film following the latter’s dementia diagnosis, considering the condition may have been affecting Willis on some level for decades, and Smith laments the possibility of having held any influence of Willis’ condition against him.
  • Creator Killer:
    • By itself it would likely have been regarded as just a disappointment after the generally well-received Clerks II and Zack and Miri Make a Porno. However, when combined with Smith's very public meltdown over his getting ejected from a plane, along with the bizarre Red State distribution auction and falling out with the as-of-yet-to-be-disgraced Weinstein brothers, it ended up being the final nail in the coffin for his mainstream career. He's since decided to remain strictly indie, occasionally directing for television as well, and only going back to more mainstream affairs with Clerks III, even then only because Lionsgate picked it up for distribution.
    • The brothers Mark and Robb Cullen, who wrote the movie, would be stuck in Hollywood Limbo until 2016.
  • Doing It for the Art: Kevin Smith claimed via Twitter that he took an 80% cut to make the film.
  • Executive Meddling: Inverted. Kevin Smith originally wanted to call the movie A Couple of Dicks, which the executives shot down. When he called it a cop out, they told him that was a better name, which he agreed with and decided that in this case they were smarter than him.
  • Hostility on the Set: Kevin Smith has remarked several times about how little he and Bruce Willis got along while making this movie. They had previously worked together on Live Free or Die Hard when Willis offered to do another movie. However, Smith was dismayed when he realized that Willis was only there for the money and was prone to Wag the Director, if not threats of physical violence. Smith called Willis "the unhappiest, most bitter, and meanest emo-bitch I’ve ever met at any job I’ve held down," and having been a longtime fan of his movies beforehand, he had a massive case of Broken Pedestal over working with him professionally. Willis responded to these claims by saying Smith smoked too much pot on set and wasn't sure enough of himself as a director.
  • Make-A-Wish Contribution: A Make A Wish kid plays the student driver who runs over Bruce Willis' character under the El-Train.
  • One for the Money; One for the Art: This was the first film Kevin Smith directed that he did not write. His hope was to start a Steven Soderbergh trend of personal films next to crowd pleasing mainstream films, but the results were not satisfactory to almost anyone. He did say that doing this movie gave him some clout when he went back to indie films (a financier for Red State expressly said he saw Smith next to Bruce Willis and thus took a chance on him), so it wasn't a complete waste of time.
  • Throw It In!: Seann William Scott said on Kevin Pollak's Chat Show that a lot of his scenes were improvised, such as the scene where he finishes Tracy Morgan's lines and the jail scene.
  • Troubled Production: Tensions between Kevin Smith and Bruce Willis made this a miserable shoot. Smith has said the one thing that saved the movie for him was how good-natured and funny Tracy Morgan was.
  • Wag the Director: Kevin Smith, a longtime fan of Bruce Willis who had enjoyed working with him on Live Free or Die Hard (where he had a bit part) and was initially overjoyed to hear that they would be working together again on this film, quickly found out the hard way that all of the rumors that Willis was difficult to work with were true. He dedicated entire chapters in his books Tough Shit and Kevin Smith's Secret Stash: The Definitive Visual History (in which he referred to working with Willis as "true darkness") to several key incidents.
    • On the first day, he outright told Smith than that he hated his fans and deliberately flubbed or half-assed his lines to waste time. He outright refused to take any direction such as standing on his lighting mark for outdoor shots, and frequently wandered off to the catering table when bored. And when you're one half of a buddy cop movie, this is especially bad.
    • Willis also berated Smith for not knowing the proper name for the specific camera lens he wanted for a green screen shot and even threatened to punch him (which he denied), then continued to verbally abuse him when Smith dared to ask him to read a line like his character from Moonlighting. Willis later responded to these stories by criticizing Smith for being too lax on the shoot and smoking too much pot (which, if Smith's own claims are true, wouldn't be unjustified).
    • According to Smith, Willis' control over production extended to the rest of the cast. On the first day of shooting, Smith let Tracy Morgan improvise his lines, which seemed to have so infuriated Willis that it got them off on the wrong foot right away. Smith knew that he couldn't contradict Willis, because he was a big enough star that he could've gotten Smith fired from the film, though Smith was so miserable on set that he said he wouldn't have minded if Willis did that.
  • What Could Have Been:
    • Warner Bros. picked up the project in turnaround in 2008 from Gold Circle Films, where it had been in development with Robin Williams and James Gandolfini in the lead roles.
    • Ben Affleck and Jason Mewes were offered roles, but weren't free. The latter of whom had recently relapsed and couldn't do the role required for him, which was stunt driving as a member of a gang.
  • Working Title: A Couple of Dicks, A Couple of Cops, Cop Suckers.

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