This movie could only have been set in the 1980's. Any later, and Brantley wouldn't have gotten away with his scheme for even a day -- quick email to HR, and mystery solved! Also, despite most of the corporate executives being portrayed as either wicked or as sycophantic buffoons, it's still treated as a great victory for Brantley to become one of them. Try having that fairy tale storyline in the "Reality Bites" era a few years later, and see how far it gets you.
You don't mind, though, because Michael J Fox is just so damned likable. Combine his natural charm with a pretty blonde love interest with eyes to die for and a catchy soundtrack full of saxophones, keyboards, and Night Ranger, and you've got the recipe for a pleasant little film -- it's wildly unbelievable but tons of fun to watch.
I wish I had a copy of Doc Hollywood handy. . .