Listed as one of George Clooney's favorite films on his resumé. He said, "It was the first time where I had a say, and it was the first good screenplay I'd read where I just went 'That's it.' Even though it didn't do very well box-office wise, we sort of tanked again, it was a really good film."
Michael Keaton reprised his role as Ray Nicolette in a small cameo. He originally played him in another Elmore Leonard novel-adapted film, Jackie Brown (1997).
During their DVD commentary, Steven Soderbergh and screenwriter Scott Frank reveal that the cast members ad-libbed several memorable lines in the script. Don Cheadle wrote the line, "in a situation like this, there's a high potentiality for the common motherfucker to bitch out."
The mug shot of Jack Foley ( George Clooney ) (about which Karen (Jennifer Lopez) says, "He doesn't even look like that") is the mug shot of Clooney's character Seth Gecko from From Dusk Till Dawn (1996). Along with the Ray Nicolette character, this is the film's second reference to films by Quentin Tarantino.
The trunk scene was shot forty-five times. However, none of these takes were used in the final cut, as the test audience disliked the long single take. The scene, as it appears in the movie, was a re-shoot. The original long take is available in the DVD extras.