Martin Scorsese
2006
151 minutes
This is another film that you're a bit embarrassed that you have never seen. You haven't been deliberately avoiding it or anything. In fact, quite the opposite. You've been wanting to watch this for years, but it is long and has largely been unavailable without some kind of obnoxious rental or a subscription to some streaming service that only has like ten films on it or something. When you add this to your belated wife's deep distrust and dislike of Scorsese and a mutual weariness for Boston bullshit, that all adds up to you prioritizing a lot of other things before this. Every fucking Boston friend of yours has probably Whitey Bulger Red Sox Pats Tawm fakkin' Brady Matt Damon Ben Affleck count the rings seen and internalized this film more times than you can count. Aside from a few clumsy memes, you're going to go into this raw.
And you're generally going to like it.
Someone could have sold you on this much earlier if you knew Ray Winstone had a major part in it. That's going to make the movie for you. His accent is terrible and confusing, but he will be the best part of the film for you. You're also pretty tolerant of Leonardo DiCaprio. By some miracle you saw him early in The Basketball Diaries and never entirely wrote him off as a Hollywood pretty-boy when he was hamming it up in Titanic and other shit-you-didn't-care-about-but-felt-obligated. Despising current or former Hollywood pretty-boys is a mistake of youth, and you're now old enough to have this mostly out of your system. Some of those dudes have actual acting chops.
This will have one of the flaws of Scorsese films. You are not necessarily supposed to like these characters. You shouldn't find them so repulsive that you can't identify with their feeling and motivations, but you should be aware at all times that these are all troubled people that you don't want to be like. No matter how quotable they are or relatable they are in some moment, don't be that guy. Much of liking or hating Scorsese for the wrong reasons stems from thinking you're supposed to emulate his amoral and often despicable characters. Don't be a grown man watching these films and fantasizing about how cool it would be to have a job being one of these pricks. You've already worked jobs where maximizing your income involved occasionally having to be an amoral piece of shit. There was no glory or high stakes, only trivially more beneficial amounts of money. Being presented with such conflicts in real life is mentally taxing and wearisome. You're slightly more jealous of people who have always had an opportunity to walk the high road on a tightrope with a safety net.
One thing Scorsese is very good at is communicating some of the bizarro logic of criminal enterprises. In an early scene, Leo (who is a mob nepo-baby) goes into a bar with his idiot cousin who is his gateway into infiltrating the mob. The criminals knew and liked his uncle but are a bit wary of him, especially since his cousin is such a shithead. He orders a cranberry juice from the bar, for which he is mocked by some minor criminal bar denizen goombah, who notes this is a natural diuretiic and asks him if he's got his period. He initially seems to shrug this off and then, suddenly and shockingly and meme-ably smashes a mug into the man's face. Ray Winstone's character suddenly leaps up and corners him but stops short of giving him a beating, instead asking him numerous times if he knows who he is. He informs him that there are guys he can hit and guys he can't hit, and he's the guy who makes that decision. The man he hit is almost a guy he can't hit but not quite a guy he can't hit. So he's going to have to make a judgment call and say he can't hit him. It's a nice warning shot over the bow. Ray Winstone then informs the other guy of Leo's famous uncle, which elicits a sigh of disgust, at which point Ray Winstone punches him in the face. It's a succinct five minutes of a movie in which Scorsese establishes the black and white and grey areas of who can fuck with whom and why, and it is gorgeously done and it applies to a lot of situations you've been in or observed in the course of your life. Little moments like this are why we watch movies.
Also, in case it isn't obvious, Jack Nicholson is fun in this. The scene with him wielding an enormous realistic dick-shaped dildo in an adult theater is iconic. It's so fucking ridiculous that laughing at it seems cathartic. A perfect moment in a pretty-good film.
Time to choose something different: