Obama’s Star-Studded Playlist Outshines Trump’s Executive Holiday Extravaganza

Max Sterling, 12/20/2025Explore the cultural clash of holiday traditions as Trump’s new federal holidays collide with Obama’s influential playlists. From evolving masculinity to the rise of curated lists, discover how these trends reflect a nation in search of connection and meaning amidst changing rituals.

But the fixation on holiday quotas barely scratches the surface. Behind the official decrees and blustering social media skirmishes, a far quieter battle is shaping the rhythm of the season. Americans still crave ritual, yet increasingly look to curated lists, not calendars, to make sense of their time—Spotify’s year-end wrap-ups and digital mixtapes seem to carry as much authority as any government issuing days off.

Credit Barack Obama with helping tip the cultural scales. The former president’s annual compendium of favorite books, films, and records drops each winter with the practiced showmanship of a statesman-turned-tastemaker. Forget laundry lists—these recommendations function more like artful temperature checks on the country’s collective mood. Just look at the latest playlist: “Paper Girl” and “Flashlight” parked next to a civics flex like “We The People,” all rounded off by Michelle Obama’s “The Look”—a not-so-subtle nod to the perks of power. It’s part playlist, part cultural Rosetta Stone, suggesting that reading for fun and reading for duty are no longer mutually exclusive.

And did anyone fail to notice how Obama’s picks seemed to foreshadow this year’s Oscar nods? Coincidence? Perhaps. But the overlap blurs the old lines between what’s merely enjoyable and what’s “essential,” stirring up the annual squabble over what gets counted and what—deliberately or not—finds itself excluded. Outrage, recommendations, and FOMO all get equal airtime. The process is messy, sure, but it’s an oddly satisfying mess.

Meanwhile, the 2025 soundscape careens across genres. Lady Gaga’s “Abracadabra” rumbles in with maximalist pomp, while Burna Boy, Rosalía, Chappell Roan, and Gunna keep the playlist borderless and impossibly democratic. Even hip-hop’s headline attraction—Kendrick Lamar trading lyrical haymakers with Drake—finds both parties included in the ex-president’s musical olive branch. There’s something slyly diplomatic in Obama’s refusal to take sides, a gesture that nods to inclusion without ever breaking a sweat.

It’d be naïve to think any of this is apolitical. The politics of taste—who gets the final say, who’s left on read—are always bubbling under the surface. Case in point: Lucy Dacus, missing from this year’s roster, took her absence as a snub, lobbing the “war criminal” accusation via social. Obama, for his part, let the silence drag on—a kind of ghosting tailor-made for the digital age. Everyone pretends inboxes fill up unexpectedly.

If these lists light up like a bonfire each winter—drawing together a hodgepodge crowd for a moment of unlikely kinship—the year’s conversations about masculinity stoke their own embers. Reyes Peña, a Salt Lake City tech worker, has gained a modest following for his daily Instagram dispatches: “feminine-inspired” outfits cloaked on a broad-shouldered frame. His feed, @tevistuff, is a running commentary—part fashion experiment, part cultural Rorschach test. What once earned mockery now seems, in certain circles, quietly enviable. Peña sums up the new attitude: “There’s a huge reclaiming of what it means to be ‘girly,’ and I hope it keeps going.”

The so-called “Great Softening”—a phrase that feels almost too tongue-in-cheek—marks a real tectonic shift under the old American bravado. Instead of polos and khakis, think earth-toned skirts, chunky rings, and a gender binary dissolving in slow motion. If the rightward flank doubles down on the old playbook, plenty of young men now treat accusations of queerness as a weirdly aspirational badge. TikTok’s soundbites say so, anyway: “Your boyfriend should have allegations of being gay. That’s how you know he’s a keeper.” The internet never met a nuance it couldn’t flatten, but the larger trend is tough to ignore.

Give credit where it’s long overdue—women, especially women of color, have dragged masculinity into these uncharted waters. Peña, who borrows most of his wardrobe from his partner, is matter-of-fact on this point. Every time the morning routine gets a little more experimental, it’s just another small testament to the ripple effect of decades of advocacy. Not that the country has altogether cracked the code, but the center keeps wobbling, and that matters.

With fresh holidays now jammed into the official schedule—Diwali finally secures its own statewide slot in California for 2026—“tradition” starts to feel less sacred and more like a shifting game of cultural musical chairs. A dozen new markers (Trump’s holidays, Obama’s playlists, a thousand micro-trends on TikTok) each plant their flag in the quicksand of American identity. Ritual, whether top-down or crowdsourced, never stands still.

So if the twinkling lights this season flicker a bit uncertainly, chalk it up to a country still searching for what connects, what comforts, and what comes next. Sometimes the rituals ring hollow, sometimes they spark something genuine, sometimes the playlist just skips to the next song a beat too soon. And if meaning is always one step out of reach, blame it on the never-ending chase—for a better story, a longer weekend, a tune that everyone can agree to keep on repeat. The search continues. Perhaps that’s the real tradition now.

The last days of 2025 find Americans juggling a peculiar double act—caught between the sort of traditions that sprout overnight via executive order and those born from a thousand algorithmic suggestions. The news this December: not just one, but two extra holidays, courtesy of Donald Trump’s signature, have been pasted onto the federal calendar—Christmas Eve and December 26th now sandwich the main event in a peculiarly American way. Memes abound, each riffing on the disappearing act performed by the workweek. (For the overworked masses, it’s the closest thing to federal magic.)But the fixation on holiday quotas barely scratches the surface. Behind the official decrees and blustering social media skirmishes, a far quieter battle is shaping the rhythm of the season. Americans still crave ritual, yet increasingly look to curated lists, not calendars, to make sense of their time—Spotify’s year-end wrap-ups and digital mixtapes seem to carry as much authority as any government issuing days off.Credit Barack Obama with helping tip the cultural scales. The former president’s annual compendium of favorite books, films, and records drops each winter with the practiced showmanship of a statesman-turned-tastemaker. Forget laundry lists—these recommendations function more like artful temperature checks on the country’s collective mood. Just look at the latest playlist: “Paper Girl” and “Flashlight” parked next to a civics flex like “We The People,” all rounded off by Michelle Obama’s “The Look”—a not-so-subtle nod to the perks of power. It’s part playlist, part cultural Rosetta Stone, suggesting that reading for fun and reading for duty are no longer mutually exclusive.And did anyone fail to notice how Obama’s picks seemed to foreshadow this year’s Oscar nods? Coincidence? Perhaps. But the overlap blurs the old lines between what’s merely enjoyable and what’s “essential,” stirring up the annual squabble over what gets counted and what—deliberately or not—finds itself excluded. Outrage, recommendations, and FOMO all get equal airtime. The process is messy, sure, but it’s an oddly satisfying mess.Meanwhile, the 2025 soundscape careens across genres. Lady Gaga’s “Abracadabra” rumbles in with maximalist pomp, while Burna Boy, Rosalía, Chappell Roan, and Gunna keep the playlist borderless and impossibly democratic. Even hip-hop’s headline attraction—Kendrick Lamar trading lyrical haymakers with Drake—finds both parties included in the ex-president’s musical olive branch. There’s something slyly diplomatic in Obama’s refusal to take sides, a gesture that nods to inclusion without ever breaking a sweat.It’d be naïve to think any of this is apolitical. The politics of taste—who gets the final say, who’s left on read—are always bubbling under the surface. Case in point: Lucy Dacus, missing from this year’s roster, took her absence as a snub, lobbing the “war criminal” accusation via social. Obama, for his part, let the silence drag on—a kind of ghosting tailor-made for the digital age. Everyone pretends inboxes fill up unexpectedly.If these lists light up like a bonfire each winter—drawing together a hodgepodge crowd for a moment of unlikely kinship—the year’s conversations about masculinity stoke their own embers. Reyes Peña, a Salt Lake City tech worker, has gained a modest following for his daily Instagram dispatches: “feminine-inspired” outfits cloaked on a broad-shouldered frame. His feed, @tevistuff, is a running commentary—part fashion experiment, part cultural Rorschach test. What once earned mockery now seems, in certain circles, quietly enviable. Peña sums up the new attitude: “There’s a huge reclaiming of what it means to be ‘girly,’ and I hope it keeps going.”The so-called “Great Softening”—a phrase that feels almost too tongue-in-cheek—marks a real tectonic shift under the old American bravado. Instead of polos and khakis, think earth-toned skirts, chunky rings, and a gender binary dissolving in slow motion. If the rightward flank doubles down on the old playbook, plenty of young men now treat accusations of queerness as a weirdly aspirational badge. TikTok’s soundbites say so, anyway: “Your boyfriend should have allegations of being gay. That’s how you know he’s a keeper.” The internet never met a nuance it couldn’t flatten, but the larger trend is tough to ignore.Give credit where it’s long overdue—women, especially women of color, have dragged masculinity into these uncharted waters. Peña, who borrows most of his wardrobe from his partner, is matter-of-fact on this point. Every time the morning routine gets a little more experimental, it’s just another small testament to the ripple effect of decades of advocacy. Not that the country has altogether cracked the code, but the center keeps wobbling, and that matters.With fresh holidays now jammed into the official schedule—Diwali finally secures its own statewide slot in California for 2026—“tradition” starts to feel less sacred and more like a shifting game of cultural musical chairs. A dozen new markers (Trump’s holidays, Obama’s playlists, a thousand micro-trends on TikTok) each plant their flag in the quicksand of American identity. Ritual, whether top-down or crowdsourced, never stands still.So if the twinkling lights this season flicker a bit uncertainly, chalk it up to a country still searching for what connects, what comforts, and what comes next. Sometimes the rituals ring hollow, sometimes they spark something genuine, sometimes the playlist just skips to the next song a beat too soon. And if meaning is always one step out of reach, blame it on the never-ending chase—for a better story, a longer weekend, a tune that everyone can agree to keep on repeat. The search continues. Perhaps that’s the real tradition now.