The 2025 Slappy Awards
Year-end Excellence
Our interviews with Adam Sandler, Sarah Squirm, Cameron Winter and Geese, Nathan Fielder, André 3000, 100 gecs, Mac DeMarco, Matty Matheson, Seth Rogen, Sandy Liang, Tyler, The Creator, Maya Hawke, Steven Yeun, Daniel Arnold, John C. Reilly, Conner O’Malley, Clairo, Father John Misty & more are here.
⚠️ Today’s Plane will likely be clipped in your inbox b/c we linked to a ton of things and it made the email version extra robust. Read it in your browser uninterrupted here. ⚠️
In the gloaming of every year, a.k.a. right around now, Erin and I (Jonah) like to gather with Spy Nation and splash around like a pod of 🐬 beautiful dolphins 🐬 in the bioluminescent bay that is the sletter. As we gaze at the horizon, we also take a moment to reflect on the previous 12 months.
This year BBSP celebrated its 5th anniversary. That number takes us by surprise every time we think about it. There’s so many things people make that are, like this newsletter, brilliant and unconventional, and yet they do not manage to find an audience, much less thrive and shine to the degree the Plane does. This is very crucially thanks to nobody besides you, for respecting your own quality of life so highly that you let us humbly help you to improve it, week in, week out.
What does “another year of sui generis excellence for Blackbird Spyplane, in a media environment plagued by rank mediocrity” (to quote David Remnick of The New Yorker and Will Welch of GQ, in a joint statement they released about us) actually mean in practice?
In 2025 we tapped in for unbeatable conversations with more people we admire across culture, among them Cameron Winter and Max Bassin of Geese, MJ Lenderman, and Brendan from Turnstile, Michelle Williams, Sarah Squirm, and the designers behind SC103 and Auralee.
We published a major scoop about J. Crew using A.I. to counterfeit their own vibes and made national news. Now we know what the words “Blackbird Spyplane” sound like when intoned by a Good Morning America co-host and 400 small-microphone TikTok personalities.
We celebrated the 35 Most Iconic Designs of the Spyplane Era. We expanded our definitive rankings of the 50 Slappiest Shops across the Spyplane Universe, and the New York Times asked us to share 4 of them with their readers. We published a definitive Cool Mom Style Guide that many say “changed the contemporary understanding of motherhood as relates to sauce.” And we followed that up with an equally definitive guide to the Best Japanese Clothesmakers Out. The Observer published a long, thoughtful profile of us. We helped make the year’s greatest shoe, the Moss Wanderer, in collaboration with Finland’s Tarvas and Stockholm’s Nitty Gritty Worldwide, and we celebrated the launch in Brooklyn at the great Ven.Space, where a bunch of Spyfriends new & old came through.
And of course we published profound essays on such swag-semiotical topics as: How to justify caring about clothes when times feel dystopian; What’s behind the fascinating, pervasive fetish for Bygone Blue Chip Cultural Stocks; Whether you can look cool if you never leave the house; How dumb you look when you’re on your phone, ipso facto we should tell time by church bells; How actually making things is fun, contra all the noise around generative AI; and How I spent every morning for 6 weeks reading Proust to re-balance my relationship to my own attention.
You can find a selection of these and other Spyplane Essays here.
All of which brings us to today, as we ring out 2025 with our annual celebration of the year’s best
clothesmakers,
movies,
music,
TV — psych — TV is cooked,
way that cool things you own can look,
way that jackets can fit,
geopolitical farce from a slapper-copping perspective,
ethical position that haters tell you is dead but, friends, it’s not,
and more!
First things first —
Best Newsletter of the Year
Blackbird Spyplane. You already know. There’s nothing else like it, never has been, never will be. Here’s our two-part secret. 1) We combine our great taste & extraordinary talents with an admirable humility, and 2) We put our respect for our readers above every other concern. If we’re doing our jobs right, you will feel that respect in every clause, in every flung fit, in every Photoshop, in every acronym, in every mindset. You will also feel it in the fact that we never take ad money and never use affiliate links in our new clothes coverage. No! We protect our connection to you, Spy Nation, along an uncompromised axis of Total Angelic Purity.
The contemporary media landscape and the torched economy at large have tried to condition us all to accept a baseline level of grifter dogs--t as inevitable. But then you read the Plane and you’re reminded that A Better Way is Possible.
The Coolest Way a Jacket Could Fit in 2025
Most Disconcerting and Philosophically Challenging Trend of the Year if You are a Mach 3+ Spyfriend
A non-negligible number of heretofore screamingly sauce-deficient people drifted away from the bad clothes that have long preoccupied them and instead started to flock — indiscriminately, it seemed, in many cases?? — to the kinds of small, cool, craft-focused, under-the-radar labels we’ve been celebrating here since Spyplane Year One. On the one hand, more people wearing great clothes is an obviously good thing. On the other hand, “Wack” People Can Ruin Things You Love. It’s a fascinating situation that we need to pay close, nuanced, highly discerning, yet broad-minded attention to as it develops.
The Best Way Something Cool You Own Can Look — and When it Looks this Way it Directly Counteracts the “Deluge of Arrivistes” Downsides of the Above Trend
Faded, flambéed and fricaseed. This is the singlemost important carryover principle from ‘00s Denimhead Culture: Wearing the hell out of beautiful things, and having that use manifest as patina, will always be doper than buying beautiful things and keeping them suspended in a limbo of inert store-freshness. This is true whether we’re talking about silver sneakers, black Belgian-linen jackets, or red 1990 hatchback Honda Civics.
