Inside Man is my favourite modern Spike Lee movie and is all about the carefully unfolding detail of a bank job.
It's not as good, but there's a Russell Crowe movie about a professor planning to break his wife out of prison after she's convicted of a murder, called The Next Three Days.
Heat is great and while it's not all setup for a particular job it's definitely about a criminal crew's meticulous professionalism and all the ways that can still get fucked up in the moment.
Memento possibly? Because you're working backwards it's a little different, but you're discovering the details of the plan in reverse.
Alfred Hitchcock's Rope might be an interesting one. It's almost a stage play about two students who discuss and plan a hypothetical murder with their professor, with a bit of a twist reveal.
I haven't watched it in a lot of years, but I remember Day Of The Jackal being one of the better assassination movies and spending more focus than usual on the details of the plan.
Mr Brooks is a flawed but good serial killer movie where Kevin Costner plays a philanthropist businessman struggling with an addiction to murder and is extremely exacting and well planned even when several unforseen new dynamics complicate things.
Like Memento, this might be exactly what you're looking for because you experience it with a protagonist who doesn't see the planning until it's revealed towards the end, but David Fischer's The Game has an elaborate clockwork to it and is an underrated Fincher movie.
Before The Devil Knows You're Dead was one of the last Philip Seymour Hoffman roles and is all about a pair of criminal brothers finding ways to fuck up their own plan.
Lord of War too maybe. Nicolas Cage plays an arms dealer trying to put together deals, stay out of the crosshairs of his clients, and avoid Interpol. It's got a lot of detail about the illegal arms trade and a number of improvisation scenes where things go really wrong. It's an underrated popcorn flick with some actual good critical analysis of the arms industry (as it was based on a critical book).
Plane came out a year or two ago and was a very enjoyable B movie about a passenger jet that crash lands on a dangerous island of a 'rebel militia'. It's a straight forward story of a pilot, some survivors, and eventually a few military contractors trying to execute a plan to get the plane flying again and get off the island.
Similarly, the original (1965) Flight of the Phoenix. It's got a ridiculously good ensemble cast and the whole movie is about a small group trying to survive and rebuild their plane that's crashed in the Sahara before they run out of water. Basically the original and best, more grounded version of The Martian.
American Animals is a movie in an interesting style about some college students who devised a precise and specific heist to steal valuable books from a university library. It's a true story, with a lot of focus on the planning, and the film is intercut with interviews with the real students which gives it an interesting tone.
For complete B-movie schlock the first Escape Plan features Sylvester Stallone as a guy who tests prison security by going in undercover and trying to break out. Naturally something goes wrong and he has to do it for real, so it's very focused on the planning.
