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The prep school douchebag has been played by countless actors throughout the years. Dead Poets Society, Scent of a Woman, and Rushmore all come to mind – and while The Talented Mr. Ripley isn’t about a prep school, one can surmise from the pretentious nature of the movie that (at the very least) there were two characters — Dickie Greenleaf and Freddie Miles — who both attended a high-end private school somewhere in the northeast.
Freddie is played by the ultra-talented Philip Seymour Hoffman, who is arguably one of the most versatile actors to ever live. He passed away far too soon, but his legacy lives on throughout the movies that he made. One of his most iconic roles being in The Talented Mr. Ripley.
Freddie Miles possesses a cockiness that can only come from years and years of privilege. The way he draws out sentences, slugs drinks that aren’t his, and constantly harangues Tom – all of it is so mean spirited and douchey that by the time he gets killed off you begrudgingly respect him. Take, for instance, this scene where Freddie confronts Tom about the whereabouts of Dickie.
The tartan scarf over a navy blazer with a fucking newsboy cap can only be pulled off when you’ve got a trust fund and can afford to wander aimlessly through Italy without a care in the world. God, I love it.
By this point, Tom has (spoiler alert) murdered Dickie, and Freddie is starting to connect the dots. Tom has stolen Dickie’s identity and is living off of his money in an apartment, and Freddie really steals the scene here with a comment about the decor of the place. “Did this place come furnished?” he asks Tom. “It… it doesn’t look like Dickie… it’s horrible, isn’t it? So… uh, bourgeois.”
Freddie is a classic snob, but he’s more than that when you peel back the layers of the character. He’s commentary on a topic that has been the subject of books and movies like The Great Gatsby and Titanic. Old money versus new money. You can have all of the money in the world but you cannot buy taste.
Freddie walks in a way that makes you want to simultaneously punch him in the jaw but also have an espresso with him at a cafe on the streets of Rome.
“Don’t you just want to fuck every woman you see just once?” Freddie mutters this line to himself while walking up to meet Tom and Dickie at a cafe. He refers to Tom as “Tommy,” absolutely adores going to the record store and listening to jazz albums, and rips Mr. Ripley to shreds for his clothing choices while abroad.
“God. A corduroy jacket in Italy.” I mean could you imagine? I’ve been to Italy myself and I can speak from experience – only an absolute philistine would wear corduroy there.
Freddie is a masterclass in vacation style. Here we see him sipping a drink at sea, once again ripping on Tom while he sits there stewing about it.
My favorite thing about the prep school character, and more specifically Freddie Miles, is how he just sashays through life. Never hearing the word “no” has conditioned him to believe that everything is his for the taking, and he gets away with bullying a guy like Tom because Tom isn’t privileged, he’s merely a con artist pretending to be, and a guy like Freddie can see right through the act. Hoffman plays Freddie to a tee.
I want to purse my index finger and thumb together and say “muah” like an Italian chef because Freddie is so perfect at what he does. He is a beautiful, scathingly offensive douchebag. Awful and brilliant at the same damn time. .
Image via YouTube
Respond
jduda@grandex.co
How’s the peeping, Tom?
Tommy! Tommy, Tommy, Tommy.
Your favorite douchebag’s favorite douchebag’s favorite douchebag
I want this job of yours, Tommy. I was just saying, you live in Italy, sleep in Dickie’s house, eat Dickie’s food, wear his clothes, and his father picks up the tab. If you get bored, let me know, I’ll do it!
I’d like to remind everyone that one time JohnnyD referred to Rome as “the Emerald City”. I still think about that sometimes.
Meh I definitely meant to write Eternal City. You know what I meant