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The Best Part of the Oscars Gift Bag Was Two Milano Cookies

Give me 49 cents worth of the Pepperidge Farm chocolate-stuffed sandwich cookie over a gold-plated vape pen any day

Tubs of packaged Milano cookies. David Tonelson/Shutterstock

I’ve never really understood the fascination surrounding the “Oscar gift bag” — the swag-stuffed loot bags that only the upper-tier famous receive simply for getting nominated for an Academy Award. Yes, there’s something funny about unnecessary products like a “smart bra” and “brainwave-sensing meditation headband” being foisted upon Hollywood millionaires, which Forbes reports were part of this year’s, $225,000 Oscars gift bag, but rich people inexplicably get free stuff all the time! Most of it is absurdly expensive! Insert Parasite joke here!

However, I’m willing to join the Oscars swag bag discourse this year thanks to this fun fact about the 2020 haul, per Forbes: “The cheapest item is a two-pack of dark chocolate Milano cookies, which cost $4.89 for a set of 10.” This is delightful, because I would gladly take a single pack, aka 49 cents worth of the Pepperidge Farm chocolate-stuffed sandwich cookie, over a gold-plated vape pen (apparently inspired by Leonardo DiCaprio) or amethyst-laden bath bomb. Milano cookies are truly the best swag bag cookie because they’re the classiest cookie out there.

When I was in middle school, these single-serving Milanos were a cafeteria status symbol; my mom deemed them too expensive, so the only way I’d get the cookie in my lunchbox was rarely, and only if they were purchased by the normal-sized Pepperidge Farm bag then portioned out into a Ziploc. But that act of repackaging missed the point: I remember watching as other people would delicately unwrap their sealed packs of Milano cookies, marveling at the amount of packaging (wrapper, little plastic holding cell, the stuff environmental nightmares are made from) that went into housing just four cookies. I don’t remember if the two-pack Milanos existed back then, but I do remember a friend would receive the four-pack in their lunchbox, just the right amount of cookies to gain an immeasurable power, by middle school standards: deciding who at the lunch table would benefit from their mercifully benevolent act of giving away a sole Milano a day.

Those cookies felt sophisticated and adult, and even though I’m now an adult who can afford to purchase my own cookies whenever I damn well please, I somehow never reach for the bag of Milano cookies on the shelf. It’s the two- or four-pack packaging that makes the cookie feel special — the limited portioning of the cookies gives them the air of prestige (you only need to eat two at at time).

And Milano cookies, just like the spare ones I’d scrounge from other people’s lunchboxes, are weirdly best as this type of gift. At a friend’s wedding, they made an appearance in the hotel’s welcome gift bag: accessible yet still special, effortless in a way that sourcing Levain cookies for your wedding bag is not. They felt elegant as a pre-ceremony snack, and elegant in a fit of morning-after hangover desperation. I have received countless wedding welcome bags over the years, but the Milanos are weirdly the only item I can remember being tied to that lovely act of hospitality, and that includes the way-too-bougie-in-hindsight stuff I put in the bags at my own wedding. I’m willing to bet the Hollywood A-list nudged aside all the CBD-infused crap in their Oscar swag bags and felt the same way.

In a truly bizarre attempt to join the Oscar conversation, Pepperidge Farm decided to real-time decorate Milano cookies with some of the evening’s most memorable outfits, a move I find incredibly upsetting. Because Milanos didn’t need to add stunt icing! Milano, the World’s Most Elegant Cookie, is already a star.

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