Actress Gina Gershon stated in a podcast Interview that during their bed scene, Tom Cruise knew she was extremely ticklish and tickled her so hard, they both fell off the bed. It was, in fact, the take used in the movie.
The term for the flamboyant tending of bar by Brian Flanagan (Tom Cruise) and Doug Coughlin (Bryan Brown) is "flair bartending" which is an acrobatic bar-tending skill. John Bandy, a flair bartender, trained Tom Cruise for the film.
The film was made and released four years after its source novel of the same name by Heywood Gould. Gould also penned the screenplay for this movie.
Robin Williams was considered for the role of Brian Flanagan. Williams had previously starred in Club Paradise (1986). Incidentally, Williams starred in director Roger Donaldson's next film Cadillac Man (1990). Both Club Paradise and Cocktail were filmed in Port Antonio, Jamaica.
Screenwriter Heywood Gould wrote the book and the film based on his experiences as a bartender in the late 1970's and early 1980's, a position he took as a struggling writer.