Milo Ventimiglia’s best movie doesn’t even have a Wikipedia page

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welcome to No shame November! This week, we dive into the pop culture we love (or hate) that society forbids us to do.


Listen to me. Milo Ventimiglia’s best work – everyone’s favorite shorts, Instagram is breaking the rules, Crock-Pot lawyer – is certainly not It’s us, the show that earned him three Emmy nominations. It is not either Gilmore Girls, which launched Ventimiglia and all its dark glory both into stardom and into the hearts of so many. His magnum opus is Winter vacation, a 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 suspend adulthood in the hope of a carefree winter spent skiing, partying and meeting girls. It’s one of those dimes from early 2000s movies that you’ll find buried in a stack of VHS tapes at a thrift store, the type of low-budget movie that’s now split into 10 different YouTube videos for free internet consumption. I even signed up to IMDbPro to try to find more information about this movie, but it was mostly unsuccessful. Winter vacation is truly an unknown relic from the past.

You might be wondering how, thanks to Milo’s mustache, I found him? To this day, I have no idea. But I remember looking at it on my laptop late on a Saturday night in high school. I often indulged in romantic getaway comedies to savor my last moment of freedom of the weekend before the Sunday fears ensued. Growing up, I always counted the days until those coveted two weeks off in December. And to this day, snowboarding remains a therapeutic and leisurely pastime. So when my 16 year old fantasy stumbled upon a snow-centric romantic comedy called Winter vacation, I plunged into it. And somehow enough of this random movie has lodged itself in my brain that now – over 10 years later – I’ve been thinking, “Yeah, let’s review that.”

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Baby-Faced Ventimiglia plays Matt Raymand, whose post-graduation Wall Street job and new girlfriend (played by early career Anna Faris) both fail at the last minute, leaving him without direction and swimming in. student loan debt. So Matt and his pals head west to the Rockies, shirking the responsibilities of adulthood to hit the ski slopes and take on low-paying jobs at the resort. To anyone who ever imagined giving it all up for a simpler life – which rings especially true after a year where so many people have been doing just that – Winter vacation offers an opportunity to live vicariously through Matt and his pals as they settle in a beautiful mountain town, disconnected from the hustle and bustle of city life and the mad rush of American business. Their way of life is simple and a lot of fun.

Winter vacation is cheesy, predictable, and 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 manual you can’t help but laugh. At the station’s career fair, Matt has an encounter so cute it’s like this movie made it up. He awkwardly drops a stack of flyers and – in the bustle of scrambling to retrieve the papers – meets Michelle, a blonde-haired, blue-eyed ski instructor (played by Maggie Lawson). She is who we think will eventually match Matt’s previously defined criteria for his ideal wife: 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 girl, an expert skier who drinks beer and knows how to repair cars. Put 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 managed to keep his job on Wall Street). And he looks exactly like what you would expect from any mean 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 strangely uneven components to Winter vacation. The film’s slogan 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 to give a comedic effect – no Tommy wiseau-level – but enough to notice it. Telling the entire movie, Ventimiglia does its best with the material, providing a window into Matt’s thoughts. But most of these elements are clunky and unnecessary, as the plot doesn’t require a lot of exposure to capture.

However, this adds to the beautiful campiness of Winter vacation. And funny enough, some of those hard times help to break the predictable rom-com mold. The dialogue is natural and airy with authentic performances from the entire cast. Ventimiglia, in particular, shows many flashes of that top-tier talent that we’re now so used to. And plenty of scenes exist not to move the plot forward, but to create a smoother pace and a story that feels lived, like you’re there hanging out with these characters for a night at the bar or a day on the tracks. It’s almost as if you too have decided to quit your job and join the Aspen team (something I dream of regularly). It’s all part of Winter vacationthe contagious charm.

Yet, revisiting a 20-year-old male-centric comedy, I knew better how to prepare for a misogynistic, cringe-worthy 90 minutes that wouldn’t age well at all. Winter vacation contains many ingredients of a scorching early 2000s comedy, from its tasteless 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 looks like somewhere along the way, someone put this script into a random male comedy generator and decided to market it as an ultra indulgent guy comedy. But, luckily and surprisingly, the content of the film itself never extends to this territory. This poster and this ill-fated alternative title serves as a fake. Even with an R rating, this movie has modest language, no nudity, and humor that is actually quite substantial.

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

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

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

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

With my own ski season around the corner, I found myself Winter vacation once again. There is a simple and special privacy that comes with sharing a winter cabin with your best friends, and Winter vacation the nail: beers at the local dive bar. Group dinners in a warm cabin with the crackling of the fireplace in the background. Snowball fights in the middle of the mountains. Late evenings sipping hot chocolate. All of these moments impeccably capture the allure of the ski season and the magic of winter that I look forward to all year round.

You want to bet Winter vacation will be an annual No Shame November ritual for me, as the temperature drops, 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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