Robert De Niro initially was offered the role of gangster Frank Milo, but he insisted on playing the timid Wayne instead. The mobster part went to Bill Murray.
During the filming of a fight, Bill Murray accidentally broke Robert De Niro's nose. This is the second time a comedian accidentally broke De Niro's nose. The first time occurred when Robin Williams accidentally broke De Niro's nose on the set of Awakenings (1990).
This Robert De Niro and Martin Scorsese collaboration is one of the few where Scorsese does not direct, only produced.
Began and finished filming in 1991. Although it was released almost a month after Bill Murray's Groundhog Day (1993), he had finished filming this movie before the former began filming. Universal was going to release the film in early 1992, but it ended up sitting on the shelf an extra year.