Jim Dodge (Frank Whaley) has a problem: he can't hold down a job. No matter how much he bluffs and boasts, the fact is he's a compulsive liar and that gets him into trouble with his bosses, and now his father has had enough. Jim still lives with his family, and is very happy with this arrangement, but his dad (John M. Jackson) wants him out and standing on his own two feet, and the best way to do that is to finally stick with some kind of career. Therefore he forces his son to take the last position available in town: night shift clean up boy at the local supermarket.
This John Hughes script came at a time when the successful screenwriter was winding down his directing chores, preferring to hand his material over to others; eventually, he wouldn't hand his material over to anybody as his formerly prolific output dried up somewhat mysteriously, and when he died relatively young many of his fans felt bereft that the big comeback often hoped for would never occur. But while Career Opportunities was a mishmash of his other ideas which might indicate after the blockbusting hit of Home Alone he was pretty much a spent force, in some regards it was one of his better efforts, sloppy perhaps but with interesting ideas nonetheless.
Of course, if this was recalled for anything it wasn't the script, the direction, or any other actor apart from Whaley's co-star Jennifer Connelly - not for nothing is her cleavage prominent on the poster, never mind the movie. She played troubled rich girl Josie McClennan who Jim dreams about but recognises he doesn't have a chance with, except what do you know? These are the movies and fate will bring them together. But interestingly, neither of them start out in the story especially sympathetic: we're meant to be laughing at Jim's impudence, but he's actually quite obnoxious, a darker side of Hughes smart alecky heroes in light of the way he's far from successful in life, but is blind to the faults we can see all too well. As for Josie, in her first scenes she's teasing the clients of her millionaire father (Noble Willingham) and shoplifting at Jim's new place of work.
There are two neat cameos slipped in at this stage: John Candy is welcome in one bit as the manager who Jim fools into thinking he's applying for part of the management team, and William Forsythe is Jim's new boss who barks orders at him and leaves the bewildered young man alone in the establishment for the night. He dutifully sets about cleaning up the place, but being the sort of chap he is he soon ends up fooling about with the merchandise, culminating in a spot of rollerskating in his underwear and a wedding veil. But uh-oh, he's being watched: by Josie, who fell asleep in the changing room and is now locked in with Jim until they're freed in the morning. Something many gentlemen of his age would not have much issue with in 1991, to be fair.
Before she sought to prove herself a serious actress in grim drama, Connelly was often thought of as trading on her looks, and it's true that such montages as Josie doing her own rollerskating to Betty Boo's trilling with a very tight top on were playing on her pulchritude to sustain audience interest, but she's surprisingly good when Hughes' script offers both stars serious character moments. Josie reflects she is unhappy because she cannot have the independence she needs, and makes Jim realise he needs that too, so how about they get together? Sounds like a plan, but in a late on development which smacks of desperation to have something other than consumer-based fun alternating with soul-searching, two armed robbers (Dermot Mulroney and Kieran Mulroney) show up and threaten the duo. Whereupon this is wrapped up with unseemly haste, as if Hughes thought, yup, that'll do, yet as an examination of how his traditional teens would be set adrift by adulthood Career Opportunities was genuinely intriguing. Music by Thomas Newman, though it's mostly a pop song soundtrack.