If you loved Cocktail, try Cadillac Man
A bridge between a film you've already seen and one most people haven't. Cadillac Man has roughly 5.5× fewer votes than Cocktail — it's a deeper cut, not a mainstream recommendation. Here's what they share, and what the second one does that the first one doesn't.
What they share
Both films are directed by Roger Donaldson, and they both carry the playful mood tag, and they sit in Comedy / Drama territory. If that's the register that drew you to Cocktail, the second film will land in a comparable space — through a different lens.
What Cadillac Man is
One imagines someone, somewhere, thought this was a good idea. A car salesman is given an ultimatum: sell a dozen cars in two days or lose his job. Can he juggle this challenge with his messy personal life? It's a comedy, apparently.

