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Milo Ventimiglia’s Best Movie Doesn’t Even Have a Wikipedia Page

welcome to no shame november! This week, we’re diving into the pop culture we love (or hate) that society tells us we shouldn’t.


Listen to me. Milo Ventimiglia’s best work – everyone’s favorite short-shorts, Instagram rules violation, slow cooker lawyer – is definitely not It’s us, the show that earned him three Emmy nominations. Nor is it Gilmore Girls, which propelled Ventimiglia and all its brooding glory into stardom and into the hearts of so many. His magnum opus is Winter vacationa virtually unknown 2003 romantic comedy that doesn’t even have a Wikipedia page.

Like I said, listen to me.

Winter vacation follows four recent college graduates living in Aspen. They put adulthood on hold in hopes of spending a carefree winter skiing, partying and meeting girls. It’s one of those movies from the early 2000s that you find buried in a pile of VHS tapes in a thrift store, the type of low-budget film that today is split into 10 YouTube videos. different for free consumption on the Internet. I even signed up IMDbPro to try and unearth more information about this film, but that has generally been unsuccessful. Winter vacation is truly an unknown relic of the past.

You may be wondering how, thanks to Milo’s mustache, I found it? To this day, I have no idea. But I remember watching it on my laptop late one Saturday night in high school. I often indulged in escapist romantic comedies to savor my last bit of weekend freedom before the Sunday horrors ensued. Growing up, I always counted the days until that coveted two weeks off in December. And to this day, snowboarding remains a therapeutic and leisurely hobby. So when my 16-year-old fantasy stumbled upon a snow-centric rom-com called Winter vacationI dove into it. And somehow enough of that random movie got lodged in my brain that now – over 10 years later – I thought, ‘Yeah, let’s see that again.’

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A baby-faced Ventimiglia plays Matt Raymand, whose post-college job on Wall Street and new girlfriend (played by an early-career Anna Faris) both fail at the last minute, leaving him directionless and swimming. in student loan debt. So Matt and his pals head west for the Rockies, dodging the adult responsibilities of hitting the ski slopes and taking on low-paying jobs at the resort. To anyone who’s ever imagined dropping everything for a simpler life – which rings especially true after a year of so many doing just that – Winter vacation offers the opportunity to live vicariously through Matt and his pals as they hide out in a beautiful mountain town, disconnected from city life and the rat race of corporate America. Their way of life is simple and very fun.

Winter vacation is cheesy, predictable, and I loved (almost) every minute of it. But you have to throw logic out the window and approach it with those low-budget rom-com lenses, because the moments in this movie are so classic you can’t help but laugh. At the station’s job fair, Matt experiences an encounter so cute, it’s like this movie made it up. He awkwardly drops a stack of flyers and – in the hustle and bustle of scrambling to retrieve the papers – meets Michelle, a blonde-haired, blue-eyed ski instructor (played by Maggie Lawson). She is who we are think will eventually meet the criteria previously set by Matt for his ideal woman: the “Red Truck Girl” who drives a four-wheel drive SUV with a ski rack, who is “outdoors, athletic, caring and compassionate”.

But wait! She is not your typical girl. She ends up jumping in a silver Honda, not a red truck! She is a costs daughter, an expert skier who drinks beer and knows how to fix cars. To put it more frankly, she is every female character in a male comedy. And to top it off, we learn that despite the budding chemistry between Matt and Michelle, she has a boyfriend in New York (who has managed to keep his Wall Street Jobs). And he looks exactly like what you’d expect from any nasty douchebag boyfriend from an early 2000s comedy. When Michelle reveals all of this after Matt’s failed attempt at a first kiss, the plot thickens.

“Winter Break” is cheesy, predictable, and I loved (almost) every minute of it.

There are also a number of oddly uneven components to Winter vacation. The film’s tagline is “Better Than Warm Apple Pie”, a phrase that has absolutely no relevance to any part of the film. (Michelle loves pecan pie, in case you were wondering) A handful of lines are lazily doubled for comedic effect – not Tommy Wiseau-level – but enough to notice. Narrating the entire film, Ventimiglia does his best with the material, providing a window into Matt’s thoughts. But most of them feel clunky and unnecessary, as the plot doesn’t require much exposition to grasp.

However, it adds to the lovely campiness of Winter vacation. And funny enough, some of those tough times around the edges help break the predictable rom-com mould. The dialogue is natural and airy with authentic performances from the entire cast. Ventimiglia, in particular, shows many flashes of that leading man talent to which we are now so accustomed. And many of the scenes exist not to advance the plot, but to create a more fluid pace and a story that feels lived in, like you’re right there hanging out with these characters for a night at the bar or a day on the slopes. . It’s almost as if you, too, have decided to quit your job and join the Aspen team (something I regularly dream about). It’s all part of Winter vacationher contagious charm.

Still, revisiting a 20-something male-centric comedy, I knew better be prepared for a misogynistic, cringe-worthy 90 minutes that wouldn’t age well at all. Winter vacation contains many of the ingredients of a raunchy early 2000s comedy, from its vapid alternate title — “Snow Job” (yes, really) — to its promotional poster, which features a scantily clad woman who isn’t even in the movie . Really, it seems like somewhere along the way, someone put this script in a random male comedy generator and decided to market it as an ultra-forgiving comedy for guys. But, thankfully and surprisingly, the content of the film itself never deviates from that territory. This unfortunate poster and alternative title serves as a fake. Even with an R rating, this movie has modest language, no nudity, and humor that’s actually quite substantial.

The only time I felt painfully aware of Winter vacationThe age of was in its third act, when Carter (Eddie Mills) – the group’s symbolic womanizer – is invited for coffee by Sergei (Kevin Kirkpatrick), a gay colleague. In this pointless subplot, Matt and his friends laugh at the idea of ​​going on a date with a gay man. Sergei ends up being the butt of a joke that isn’t funny at all. Later, Carter and Sergei arrive at a party, holding hands and pretending to be lovers, which is also played as a joke, then never addressed.

Despite its flaws, the film’s central message is about as timeless as it gets: follow your heart.

Despite its flaws, the film’s central message is about as timeless as it gets: follow your heart. It’s a sound philosophy that’s scattered everywhere Winter vacationwith Matt’s decision to turn down two different promising job opportunities so he can stay in Aspen, and in his pursuit of Michelle, despite her being in a long-distance relationship with a total tool who – despite his arrogance – has a whole lot more to offer in terms of financial stability.

This “follow your heart” message, corny as it sounds, is truly a timely reminder after a pandemic where priorities have shifted, and the value of human connection and personal happiness has become more precious than ever. Whether the ski bum lifestyle is right for you or not, find your Aspen, whether in a quaint suburb, a sleepy seaside town or a secluded countryside. Follow your heart, wherever your Aspen is.

With my own ski season fast approaching, I found myself engrossed in Winter vacation once again. There’s a simple, special intimacy that comes with sharing a winter cabin with your best friends, and Winter vacation Nails it: Beers at the local dive bar. Group dinners in a warm cabin with the crackling fireplace in the background. Snowball fights in the middle of the mountains. Late at night sipping hot chocolate. All of these moments impeccably capture the allure of ski season and the winter magic that I look forward to all year.

You want to bet Winter vacation will be an unashamed annual November ritual for me, as the temperature drops, the sweaters come out and I prepare for my own season of mountain adventures.

Winter vacation can be rented on Apple TV+.

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