The two biggest problems with the movie wre that you needed more character moments to understand the characters better, which would've made the movie less confusing and make the plot stronger. Second, it needed to be funnier. Jason has no concept of comedy. He relied on the actors improvising to make scenes funnier.
A lot of the problems come from bad writing. The movie should've started with more of a set up, to get to know the characters. Jumping right into the party wasn't a good idea. It also wasn't a good idea to have the movie set on the eve of the wedding. It should've been an engagement party. Having it set the night before the wedding is cliche and you end up with everything (like the father's background check on Charles) being too convenient. Also Leonard just showing up wasn't a good mood. A scene showing him before the party would've been better. It also would've made more of an impact when he shows up.
I've only seen the movie once and don't plan on watching it again, but I was confused a bit by Leonard and Williams's relationship. I think if you explained that more, the movie would've been better. Also William/Charles being a con man who was planning on marrying into the family, to steal their money wasn't done well either. What I would've done is make William and Leonard partners. They came up with the grift. William (the good looking, suave one) worked his magic to get Fiona to marry him, while Leonard is stuck living in a dump, pulling nickle and dime stuff, making ends meet and maybe owing a bad man some money. William falls for Fiona and tells Leonard that the con is off. So Leonard shows up to tbe party, hoping he can convince William to go through with the plan or he will wreck everything. You also need to set up that Bruce Davidson is a bad, dangerous man (which didn't come through enough) who maybe also has done uis fair share of screwing people over. So you go from there. I also think having Leonard walk away with some money could be a nice ending.
I just felt too much lf the movie was wasted dialogue that went on and on, when you could've condensed many scenes down in the script, which would've allowed for a few extra scenes to make the story and characters deeper.
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