The Pentagon Wars is very decent.
https://en.wikipedia.org/wiki/The_Pentagon_WarsI guess software movies are OK too, like Pirates of Silicon Valley (the generally insane behavior of the main characters), Office Space too (I would consider this to be a engineering comedy because of the salami slicer virus being a plot point), most people have seen these to death though.
Not bordering currently heavy science fiction action like the rocketeer, robocop, etc (as funny as they are).. the die hard movies are kind of engineering comedies also in a way, but too fantastical.
I mean more down to earth movies with bureaucracies, corporate politics, etc being the focal point.
Better off Ted was a good one with a good bit of the issues when engineers and corporate interact.
Interesting topic. While certainly not a comedy, my submission is the Bridge on the River Kwai. There was both a leadership and engineering dichotomy between the waring players that made it a most satisfying movie, highly recommended if you haven't yet seen it.
https://en.wikipedia.org/wiki/The_Bridge_on_the_River_Kwai
There is also the "Halt and Catch Fire" series. Not all that much in terms of comedy but it has quite a bit of engineering in it as one of the main characters is a engineer that's making a new home computer in the 80s and his wife works at Texas Instruments.
BrianHG: That is not the Dilbert TV series I was referring to, but rather the animated shorts. There was an actual TV series, see a clip:
I've been in meetings that felt a bit like this one:
OK, a bit of a stretch, but 1967 British comedy "The Plank":
Basically it's about the never ending challenges faced trying to move a plank of wood. Runs about 45min.
There is a funny (formerly) Czechoslovakian animated series "Pat a Mat", see: