Hear, Hear For ‘Sing Sing’
On the movie I can't stop thinking about, plus Gen Z men and politics, podcasts and 2024's election, insomnia, morning pages and more.
Las week was a good week for movies in mid-Missouri.
I got to see Sing Sing and The Brutalist on back-to-back days at Ragtag Cinema.
The Brutalist is the bigger, juicier release of the year, certainly the talk of all the film bros. It was recently recognized with 10 Academy Award nominations. It was also the subject of a quietly brilliant bit Oscar-related targeted takedown when it was revealed (oopsie) that it used AI in not one but two different ways. (For the record: One of them—using it to enhance the Hungarian accent—seems to be totally fine and understandable, if not absolutely pure; the second use—relying on Midjourney to create architectural drawings that were used in the film—seems to be a stickier question for those of us who’d prefer to see human work remain the province of actual humans. But I digress.) It was the subject of one of the most thoughtful discussions on a film I’ve heard in quite a long time, between The Ringer’s Sean Fennessey and Adam Nayman.
Pocket Casts
Despite all of that (and loving the 3-hour experience of watching it), it’s Sing Sing that I haven’t been able to stop thinking about.
Sing Sing is a quiet drama about a theater company within Sing Sing prison that was founded by and featured inmates as the actors in various plays. The program is real, and the film stars some of the inmates starring as themselves in the film.
Colman Domingo is the lead, in a turn that won him a Best Actor nomination. Clarence Maclin should have earned a Best Supporting Actor nomination, because he’s incredible as Domingo’s frenemy-turned-friend.
The performances in the film are not what I keep returning to (though they are fantastic). The production behind the film is not being hyped in the same way as The Brutalist. No, what keeps running through my mind are the messages that I took away from the film.
I think we like to see our own humanity shown on the big screen. And the humanity stands out in sharp relief in this film, set in one of our least humane inventions: the penitentiary. Even rock-ribbed supporters of the America’s penal system can’t deny the pervading degradation and stripping away of many of the things that make us most human; some, I’m sure, would say that is the point of all that punishment and deprivation.
It’s an effective backdrop for a story in which art—of any kind, but here acting—is an escape for these men. The acting is part of the amazing success of the program; other arts can be (and often are by design) solitary endeavors. But acting, as the film depicts, requires this letting go—of control, of the illusion of control, of self—and it must be done in front of other people, and if done well, with the intention of making them feel things, to transport them even though it’s so often these inmates on stage who want to be anywhere else.
The acting scenes are the things that would have inspired eyerolls and self-consciousness in me as a young child. My mom is fond of telling the story of one of my elementary school plays, in which I was supposed to play something (I’m wanting to say maybe it was something problematic, like a Native American in some sort of Thanksgiving-themed show), and for which I’d begged her to attend, despite being very pregnant. And then on the night of the big show, I … was nowhere to be found. Just hanging out on the side of the show, having decided I was too shy to go on stage.
I was able to push beyond that discomfort in my teenage years for church-related acting, namely Judgment House (a macabre series of vignettes that depict slices of life, tragic deaths, and then confrontation at the Pearly Gates with a will-He-won’t-He moment of gaining admission to Heaven. I was destined for Hell, because I was one of the few non-theatrical types who would do the weeping and gnashing of teeth expected when told, “YOUR SENTENCE IS ETERNITY IN HELL” and do a dramatic plunge off the stage as if I’d been cast into the abyss. (It’s not a great look for churches, if I’m being honest, and if you want a great depiction of it, I can’t recommend Jason Kirk’s Hell Is A World Without You.)
But the inherent self-seriousness that we carry ourselves with (many of us, that is) is dialed up to 11 in these prison scenes, with these inmates, who in one moment are beating their chests, to let others in the yard know, Denzel-style, that “King Kong ain’t got shit on me!” Then to see these men, these hard and scary men, hard and scary by necessity and for survival, turn to these silly, goofy, childish acting exercises is like magic. You can see the beginnings of it then: They’re becoming someone else, and it’s a beautiful softening, a beautiful release of whatever you just know is pent up inside them.
The vulnerability would still be striking were the film not set in prison due to the other meaningful reality of their existence: It’s overwhelming male. A male prison with male guards and wardens. Testosterone everywhere, so much so they’re practically swimming in it.
Quieter, more contemplative acting exercises show them sitting in a circle, eyes closed, listening to prompts that instruct them to go somewhere in their minds, somewhere happy, and take notices of the details. Then they begin sharing, and when you hear the things that matter to these men—the things that they’ve been forced to do without for so long—it’s hard to imagine a more sensitive conversation in an all-male setting happening in the wild. They bare parts of themselves. They allow themselves to break down. There are no pretensions. And in their undesirable positions, they have something richer than many men out there could ever dream of.
I felt that acutely as I watched, feeling a tightness in my chest and moistening of my eyes, hearing those around me in the dark share a sniffle that said, “Me, too. It got me, too.” I thought about a recent therapy session that saw me cry and cry and cry, all while trying (and failing) valiantly not to cry, when I tried to relay these insecurities around manliness I still struggled with since my dad’s death: how tools and other markers of manly men left me feeling inadequate and wishing for my dad’s reassurance, and how mechanical know-how (or lack thereof) brought up both shame in the not knowing and longing for the ability to call and confess my ignorance to one person and one person only: my dad. I thought of how choking down tears and trying to keep my discomfort cause discomfort in him kept me from saying things to him before he passed, how it keeps me from talking about it to my family any and every time memories spring to mind.
Art makes us human, and in our humanity, we can make and find beauty in beauty-less places. Art can help us get in touch with our feelings. Art can level the playing field. Art can tame the wild and sand off rough edges. All of us men need this, not just inmates, not just gangsters, not just bruisers.
This film didn’t just feature men coming to grips with their emotions as some subplot; it was the film. And while that might seem to be “less” film than what The Brutalist has to offer, it’s the very reason Sing Sing reached me at my deepest levels and hasn’t left my thoughts for long since.
Ten Worth Your Time
- Amid the flurry of last-minute familial pardons by Joe Biden and first-order-of-business pardons of 1,500 January 6 rioters by Trump, you might have missed one particular pardon: Ross Ulbricht. He was the creator of the dark web’s infamous Silk Road, the easy-peasy Amazon-like one-stop shop for illicit shit. Drugs? Yep. Guns? Sure. Poisons? How many poisons would you like, good sir, because we have many. It was the site that really brought to my attention Bitcoin, but honestly, in this current moment of nonstop talk about Bitcoin, I’d forgotten that’s where I first learned of it. Anyhoo, he’s out now. And it reminded me of this epic two-part story reported out by WIRED back in the 2015 that was just chef’s kiss so well done. Admittedly, I was into the story; I’d go on to read Nick Bilton’s *American Kingpin,*of which there’s a hardcover around here somewhere in the stacks. But this is just a big, juicy magazine story of the sort that you don’t see too often these days. (H/t to WIRED’s newsletter for pulling this one out of the archive and putting it in front of me again.)
- Honestly, I didn’t know what to make of this essay from The Point. I saw it’s general topic—Gen Z men and their turn to Trump—and assumed I knew where it would go, but it was a more nuanced depiction of what motivates these young men. The main takeaway was the sense of yearning for something and finding the offerings of current-day liberal conventional wisdom to be lacking. It’s safe to say I don’t agree with many of these young men’s opinions and interpretations of the world around them, but I respect the author’s attempt to capture it, to open her eyes and ears to what they are saying about themselves because, even if we might disagree with some of their conclusions, it’s important to know how they view themselves and their cause. They overlook a lot that I wouldn’t, personally, but it feels meaningful to catch a glimpse of what they see and acknowledge and what they sweep away.
- Links I Would Gchat You If We Were Friends continues its unbroken streak of awesomeness, and it’s shared a recent opus of a story from Bloomberg with seven (!) writers on the byline, all in service of a deep dive in the podcasters who helped Trump win the election. This is the same general underlying examination as was conducted in The Point essay, but it gives greater credence to the notion that maybe, yes, this was the Podcast Election. For the record, despite having listened to more than a month’s worth of podcasts last year, I have never listened to a second of any of these and only know of Joe Rogan’s by name. You can (and should) access the article through the Links newsletter because it’s so graciously included a gift link to the article.
- Speaking of podcasts I’ve never listened to, Chapo Traphouse is another blind spot. This Vanity Fairprofile of its members after the Democrats lost the 2024 election, but the podcast lost its way after Bernie lost the primary in 2020. It felt of a piece with the article from The Point in the sense of broadly applicable dissatisfaction with the messaging of Liberals/The Left/Democrats, and though it stopped short of saying that’s why people are flocking to Trump and those on the right, it definitely took aim at those closer in ideology for not being closer to them.
- This is a slightly older piece, but I’ve found a lot of value in some of Teen Vogue’s reporting on political issues. This one resonated with me because it just sounded so familiar to what I witnessed in neighboring Wyoming. The short description is a rural community college that provided a lot of value to its community and the wider region came under fire for basically existing as an institution of higher education. The part that reminded me of Wyoming was the existence of politics already staunchly conservative and led by one party yet that not being enough. From the story:
At first glance, the NIC accreditation crisis looks like yet another conservative attack on institutions that teach ideas they don’t like. But NIC is not the New College in Florida, the small liberal arts college Ron DeSantis targeted for takeover. It is not some infamously radical institution like Evergreen State, where student protesters shut down campus over a white professor’s resistance to a diversity event. It is a community college that offers mostly technical degrees in a county where registered Democrats comprise 10 percent of the population. Christa Hazel, a NIC alum and founder of the citizen’s watchdog group SaveNIC, put it: “Who is for woke right now in North Idaho?”
- The first week of the Trump presidency 2.0 flew by in a flurry of news notifications, and all I could think was, “My phone won’t make it through the first 6 months of this before simply melting into a mangled heap of metal.” Despite the blazing quickness with which some of Trump’s worst ideas were put into motion, there was just a feeling of, “Well, sure. Of course he did.” And very little surprised me. That’s kind of the gist of this New York Times piece about many of the women who organized the protests in 2017 in response to Trump’s first term beginning and a where-are-they-now? framing for 2025. Their minds haven’t really changed—they still find him terrible. But they don’t have the energy to protest like they did last time, namely because they felt it was largely fruitless. It was an interesting story more for what wasn’t there and didn’t happen than what actually did. Full disclosure: I mostly chose this piece because it was written by Charles Homans, who got his start at the same Wyoming paper I did and was so nice to me when I reached out to say hello years ago.
- The other night, I watched the film adaptation of Tinker, Tailor, Soldier, Spy because, quite simply, spy stories rule. I love the film and the book, which might have been why one of the first books I consumed in 2025 was the audiobook version of Ben Macintyre’s Spy Among Friends, the tale of Britain’s greatest Cold War traitor, Kim Philby. It is a fantastic book, made even better that it’s describing actual history and not some fiction writer’s best efforts to conjure up mystery and intrigue and the highest of stakes. That was why I was excited to see this—what to call it—not an excerpt but rather a super brief and modified version of different chunks of his book for Airmail. One gets a good idea of the treachery of Philby from this just-the-highlights treatment, and should you enjoy it, there’s so very much more where that came from.
- Getting this email to you a day late found me up late (for me) last night, well after midnight. One might wondering: Was I struggling with a bout of insomnia? Nope, dear reader; I’ve bragged many times that falling asleep and staying asleep might very well be my superpowers. I was very groggy last night, and what’s more, without the slightest effort on my part, I would have been able to sleep. So I’d be lying if I said I’d never wondered about insomnia. Like, what’s that all about? In truth, I’ve kind of fetishized it in a pick-and-choose way that probably doesn’t resemble reality: I’ve sometimes found myself thinking “There’s something too this whole insomnia thing” when I’m envious of creative types who just work instead of sleep in the same way I might flirt with the idea of prison not sounding so bad if I really needed to catch up on my reading and writing. So I was more than ready to hear what Adam Gopnik had to say about the affliction in The New Yorker. And as I suspected, I was brought up quickly, reminded that no, you don’t actually want any part of insomnia and should cherish your sleeping superpowers. But this is an entertaining read, no matter whether you’re able to sleep at night or no.
- I’ve talked about journaling more in 2025, and that’s why I couldn’t help but find a few of The Defector’s staff chronicling their attempt at working through Julia Cameron’s The Artist’s Way as delightful and charming and honest and relatable. One of the mainstays of TAW is “morning pages,” Cameron’s name for three pages of writing first thing in our day. Unmediated, unvarnished, just blurted out. The reality is: It’s really tough to write three pages longhand for most of us keyboard-peckers these days. They bitch about it endlessly, and I loved it. It reads so casually, so conversationally, and it made me laugh out loud more than a few times.
- I’m still thinking a lot about David Lynch since his passing. That’s due, in part, because I’m watching his final major project, Twin Peaks: The Return, for the first time. I read a ton of coverage after his death, but this one stuck with me as particularly sweet. It’s about Mary Reber, the real-life owner of Laura Palmer’s house in Lynch’s Twin Peaks universe. Even before his death, fans had flocked to the house, to see this influential spot in the storytelling that meant so much to them. The concept reminded me of the classic John Jeremiah Sullivan essay in GQ about buying a house in North Carolina that would become a filming location for the show One Tree Hill, as one of the character’s home. He talked about how fans would make the pilgrimage to see it, because it’s just something we do, to feel connected through mere physical proximity to a place where something happened once upon a time ago (even a fictional something in a fictional ago). Reading this interview with Reber makes clear she has a sweetness that Lynch would have liked; she owes these fans nothing, but she gets why they come. It feels nice to know that someone as beloved as Lynch, known for his generosity and kindness, could have found a shooting location owned by someone who vibrated at his same frequency.
More From Me
Over on my blog, I’ve been writing about various topics of interest to me.
JetPens Recommendations for 2025
Robert Caro's Personal Library
Culture Diary
Here’s a collection of what I’ve been consuming in the past week.
The legend for my list was stolen from Steven Soderbergh, where ALL CAPS represents a movie, Sentence Case is a TV show, ALL CAPS ITALICS is a short film, Italics is a book, and bold is a live performance or show. A number in parentheses after a TV show highlights how many episodes I watched. An asterisk after an entry means it’s a rewatch. The source of the movie or show, whether streaming service, physical media, or in theaters, is shown in parentheses as well.