Thomas Jane was brought into the project by original director Wayne Kramer. When Kramer left the project, Jane suggested Sylvester Stallone to hire Walter Hill. After Hill took over directorial duties, Joel Silver came on board the project and fired Jane because he wanted an ethnic actor for the other lead role. Sung Kang was subsequently cast.
When in the car on the way to the party in search of Baptiste, one of the pictures on the phone are of Sylvester Stallone as John Rambo in First Blood (1982).
Walter Hill said he wanted to have fun with the genre:
"We're not breaking new ground. We're trying to be entertaining within a format that's familiar. There's a kind of ice skating that goes on where you must let the audience know that you're not taking yourself too seriously. But at the same time, the jokes are funny but the bullets are real. The jeopardy has to be real. When it gets outlandish, there needs to be no drift into parody - self-parody, maybe inevitable for old directors".
"We're not breaking new ground. We're trying to be entertaining within a format that's familiar. There's a kind of ice skating that goes on where you must let the audience know that you're not taking yourself too seriously. But at the same time, the jokes are funny but the bullets are real. The jeopardy has to be real. When it gets outlandish, there needs to be no drift into parody - self-parody, maybe inevitable for old directors".
Sylvester Stallone's character is named James "Jimmy Bobo" Bonomo. In Oscar (1991), Stallone's character talked about his first job, working for James "Jumpin' Jimmy" Bonomo. In both movies, Stallone has a daughter named Lisa, and both films include hitmen as central characters.