Waydowntown (2000) 3.5/4

Four co-workers make a bet to see who can survive the longest without leaving Calgary's Plus 15 system in this maniacal comedic romp. For those unfamiliar with Calgary, the Plus 15, which takes its name from being 15 feet above the street, is a walkway system downtown which connects a huge chunk of Calgary and theoretically you COULD go a long long time without ever going outdoors since it connects to shopping centers and apartment complexes. So since all four friends have apartments within the grid, this wager could potentially take days (or over a year, which is what one character previously conquered). It's claustrophobic insanity at its best.
The film also takes time to show a satirical view of office boredom. One character throughout the course of the film staples cards with teamwork-booster slogans to his chest (and he's not even part of the bet!). Another has the dubious job of following the geriatric owner around to keep his kleptomaniacal habits under control.
Tom, the hero of the story, tries to keep everyone's lives under control between his pot-induced airborne journeys through TD Square. He tries to keep coworkers from cheating on their fiances, botch stapler man's suicide attempts, and patch up issues with a love-sick flower boy and his hyperactive girlfriend.
We are in rarely movie-attempted territory. Indoor lifestyles are usually seen through a futuristic lens (ex: Logan's Run) when agoraphobic jobs are very much a current reality.
This is a genuinely funny movie, and that's never a bad thing because if we can't see the humour in our lives, we might as well start stapling things to ourselves.