Nothing about this movie makes any sense
There are many problems with this movie.
If a movie is good, I can overlook some problems - heck, many of the 'great classics' of the eighties are full of problems, plotholes, nonsensical things and more.
However, the biggest problem with this movie, in my opinion (!), is that this..
..movidoesn't very well.
FLOW.
I was trying to mimic a bit how clunky this movie is by writing in a really clunky way as well, but I can't do it justice. The movie starts slow, awful, nonsensical and weird, not to mention boring.
'Sports' is the most boring thing you can put to a movie, which should be able to express escapism to the fullest, which means anything in the Universe and Beyond should be possible to see in a movie. What do we see? A boring baseball match, unexplained TRAIN slowly moving about the screen, stopping that uninteresting match, making it even more boring, barfight and a prison. If you can endure the ridiculously zoomed-in camerawork and bad directing (I never usually notice 'directing', but there were so many odd choices, even I could notice it)..
..you can finally get to the point where the premise starts being explained.
Let's talk about this ridiculous, over-used premise (I have read and seen so many stories where someone has to spend a lot of money or they won't get any, yada yada).
So he has to spend 30 million to get 300 million. He could also use the 'wimp clause' to get 1 million (almost 3 million in today's money - what can you reasonably buy with 30 or 300 million that you can't with 3? I mean, you could 'secure your life' very comfortably with 3 million and still have lots of 'play-around' money you can throw away without losing anything important).
Now, this kind of very STRICT rules would require CONSTANT observation, almost 'surveillance' level stuff, every single receipt counted for, every single action and word he utters observed, listened to, captured, and so on.
This premise would require a TEAM of experts that make SURE Richard Pryor's character doesn't make even one mistake.
Otherwise, he can cheat SO easily, don't you think? One back alley deal with someone to hold 15 million in some made-up corporation or trust in someone else's name, and then manufacture made-up receipts or whatnot..
Also, what's to stop him from KEEPING the 30 million and doing whatever he wants with it?
(It's kinda ridiculous that it's CASH anyway, but whatever)
I mean, once he has it, who's gonna stop him, if he decides to fly to some exotic tax-heaven country, change his name and appearance (plastic surgery isn't expensive if you have 30 million), just 'handle' his money from thereon and live happily ever after with ever-expanding fortune (playing the stock market alone would increase it easily to 100 million in the eighties, if you know what you're doing - check 'Gordon Gecko' for reference)..
The most irritating point about all of this is that it's all his decision. Why is he allowed to OVERpay for anything and everything? Then why offer such small sums?
The point here is, if he's ALLOWED TO CUSTOMIZE what he pays to people, WHY NOT PAY THE MAXIMUM POSSIBLE AMOUNT instead of 5000 bucks? This makes no sense. He just comes up with random sums, but nothing in the movie explains why they HAVE to be those sums, or why THOSE amounts of money make some kind of sense (they don't).
He pays the hotel 2 million bucks to stay there, but why not pay 5 million? What's stopping that? Why is he even allowed to pay 2 million for something that should cost only 100 000?
If he's allowed to OVERPAY, then he can just buy 1 hooker, pay 30 million for her services at the end of the month, and he has 300 million.
This movie makes NO sense on so, SO many levels, I can't even try to begin to start listing it all.
It's also rare to see John Candy, perhaps the most 'endearing', 'lovable', etc. actor and usually characters as well, be this annoying, irritating and horrible to watch. I LOVE John Candy, I have watched about everything he's in, even the duds, but never have I hated him before this movie. Holy cow, how can it even be possible?
This movie is so badly directed, it barely flows at all, Pryor's character is the same, always-screaming goofball he's in every other movie, these two have no harmonious energy (I REFUSE to use the word 'chemistry', as that means something completely else, and how well two people/actors/characters gel in a movie has nothing to do with anything 'chemistrylike')..
The premise also gets very tiresome very quickly. So he has to spend a lot of money without gaining assets or giving it away - but he CAN buy lunches to people? What? Isn't that GIVING IT AWAY?
Can he buy assets, then give THOSE away? (which is what 'buying lunch for someone else IS)
He was even thinking of buying some diamond necklace for the man-faced short-haired fema-fascist hag, but she, of course, being a vegana carrier, is SO noble, she would NEVER accept an expensive gift while there are people starving..