The trunk scene was shot 45 times. However, none of these takes were used in the final cut, as the test audience dislike the long single take. The scene as it appears in the movie was a re-shoot. The original long take is available on the DVD extras.
When Jack sees the photo of Karen's father, he remarks that he has a "cop's face". In real life, Dennis Farina, who plays Marshall Sisco, is a former Chicago police officer. As an actor Farina has had several roles as a cop.
During their DVD commentary, director Steven Soderbergh and writer Scott Frank reveal that the actors 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."
Maurice's comment to the Midge the maid - "...you're gonna be a dead Hazel..." - is most likely a reference to the television show of that name. The show Hazel (1961) starred Shirley Booth and ran from 1961 - 1966.
Sandra Bullock almost got the part of Karen Sisco but Steven Soderbergh was against it. He said: "I spent some time with Clooney and Bullock, and they actually did have a great chemistry. But it was for the wrong movie. I'm sure they could do a movie together. But not an Elmore Leonard movie." Clooney and Bullock appear together in 2013 movie Gravity (2013)
Foley appealed to George Clooney because as a boy, his heroes in crime films were always the bank robbers. He liked "the Cagneys and the Bogarts and Steve McQueen. The guys who were kind of bad who you rooted for. And when I read this I thought this guy is robbing a bank but you really want him to get away with it."
Steven Soderbergh shot the initial scene between Karen and Foley in a trunk because he liked the forced intimacy it generated between the two strangers. Before the scene was over, he knew they had spent enough time in each other's heads that the intimacy between them was real now. And that can only lead to love. Which is why the film works.
Out of Sight (1998) is one of George Clooney's favourite films on his resume. 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."