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

8 min read
fairly easy
Hint: It came in the avalanche of American Pie imitators.
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.

Hear me out. The finest work of Milo Ventimiglia — everyone's favorite short-shorts-wearing, Instagram rule-breaking , Crock-Pot advocate — is most definitely not This Is Us, the show that earned him three Emmy nominations. Nor is it Gilmore Girls, which launched Ventimiglia and all his brooding glory into both stardom and the hearts of so many. His magnum opus is Winter Break, a virtually unknown 2003 romantic comedy that doesn't even have a Wikipedia page.

As I said, hear me out.

Winter Break follows four recent college grads living in Aspen. They're putting adulthood on hold in hopes of a care-free winter spent skiing, partying, and meeting girls. It's one of those dime-a-dozen early 2000s movies you'd find buried in a pile of VHS tapes at a thrift store, the type of low-budget flick that's nowadays split into 10 different YouTube videos for free internet consumption. I even signed up for IMDbPro to try and unearth some more information about this movie, but it proved mostly unsuccessful. Winter Break is truly an unknown relic of the past.

You might be asking how — by the grace of Milo's mustache — did I find it? To this day, I have no idea. But I do remember watching it on my laptop late one Saturday night in high school. I'd often indulge in escapist rom-coms to savor my last bit of weekend freedom before the Sunday scaries ensued. Growing up, I always counted down the days to those coveted two weeks off in December. And to this day, snowboarding remains a therapeutic, tranquil hobby. So when my fantasist 16-year-old self stumbled upon a snow-centric rom-com called Winter Break, I dove right in. And somehow, enough of this random movie lodged itself in my brain that now — more than 10 years later — I thought, 'Yeah, let's revisit this.'

A baby-faced Ventimiglia plays Matt Raymand, whose post-grad Wall Street job and new…
Jacob Lauing
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