Well, my first thought is the book Roadwork by Stephen King (part of the Bachmann books), though that'd be me a couple of years ago, would be whiney, and is also a book, not a film or game. So let's move on.
I have a physics degree and a short trimmed beard, so half life pops into my head, though I don't work in a badass secret research facility, and I'm pretty sure aliens could kick my ass. Relevant games are hard.
Films though, films are more promising. Office Space does a good job of capturing my feelings on work and the 'rat race'. And I could also be real sneaky and say Groundhog Day, due to the repetitiveness of it all (this isn't a complaint though, I'm happy with the routine).