In the movie adaption, Tom Cruise played Brian Flanagan, a struggling business student turned “flair” bartender in New York City. Obviously, Cruise’s version of the character is an attractive man in his mid-twenties, but in the original novel by Heywood Gould, Brian is described as a “38-year-old weirdo in a field jacket with greasy, graying hair hanging over his collar, his blue eyes streaked like the red sky at morning." This is because the book is semi-autobiographical, and was inspired by Gould’s years bartending to support his failing writing career. In an interview with Chicago Tribune, the author said: “I was in my late 30s, and I was drinking pretty good, and I was starting to feel like I was missing the boat. The character in the book is an older guy who has been around and starting to feel that he's pretty washed-up." However, Disney execs felt the character should be younger, pressuring Gould until he relented.
Despite the age difference, it’s virtually impossible to imagine anyone else in the lead role other than Cruise. However, Disney initially weren’t keen on casting the actor. Recalling one of his early meetings with Disney bigwigs Michael Eisner and Jeffrey Katzenberg, Gould explained: “Someone mentioned that this might be a good vehicle for Tom Cruise, but Eisner said ‘He'll never do this, don't waste your time, he can't play this part.' And then Katzenberg says, 'Well, he's really interested in doing it,' and without skipping a beat Eisner says, 'He's perfect for it, a perfect fit!' That's the movie business: I hate him, I love him; I love him, I hate him!" Jim Carrey and Charlie Sheen were also considered.
Elisabeth Shue eventually won the part of Cruise’s love interest Jordan, the waitress and wannabe artist he falls in love with in Jamaica. However, plenty of other popular 80's stars were interested in the role, including Ally Sheedy, Demi Moore, Jennifer Grey, Jodie Foster, Sarah Jessica Parker, and Daryl Hannah. The role was first offered to Molly Ringwald, then Heather Graham, who also had to turn it down due to scheduling conflicts with License to Drive.
Co-star Bryan Brown admitted further changes were made when Tom Cruise came on-board, saying: “The studio made the changes to protect the star and it became a much slighter movie because of it."
Kelly Lynch, who played Doug’s wife Kerry Coughlin, told The A.V Club: " was actually a really complicated story about the ’80s and power and money, and it was really re-edited where they completely lost my character’s backstory—her low self-esteem, who her father was, why she was this person that she was—but it was obviously a really successful movie, if not as good as it could’ve been. It was written by the guy who wrote Fort Apache The Bronx, and it was a much darker movie, but Disney took it, reshot about a third of it, and turned it into flipping the bottles and this and that."