All through December, we’re featuring Longreads’ Best of 2020. In an unprecedented, strange, and chaotic year, we’ve leaned on writers’ reflections and commentaries on the world around us to help us make sense of moments, of our lives. We revisited a wide range of arts and culture stories featured by the team this year and selected eight favorites that resonated with us.

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I’ve always loved how Teju Cole observes and moves through our world: a flâneur of modern life, always with a notebook or a camera in hand. Here, we follow Cole on a pilgrimage to Italy as he chases the life of Caravaggio, an artist (and fugitive and murderer) whose emotionally charged, often violent scenes and chiaroscuro technique I studied closely in my AP Art History class. In Rome and Milan, Cole revisits Caravaggio’s paintings “to learn the truth about doom” — to sit with unease, and to experience the artist’s pain and turmoil (“I would find in him the reprieve certain artists can offer us in dark times”).

Cole then travels south, to Naples and along the coast of Sicily, and later to Malta, to the places where the painter spent his exile; he captures both the mundanity and intimacy of encounters with guides and strangers, like his meeting in Syracuse with D., a young migrant who arrived by boat from Libya eight months earlier. (They share a silent, beautiful moment with “The Burial of St. Lucy.”) Part-travelogue, part-profile, part-art criticism, and part-commentary on the ills and horrors of our world, it’s a stunning piece with masterful scope, but also turns inward — a read you’ll likely sit with quietly long after you’ve finished.

I sat on a bench in the middle of the room, the two paintings set at a right angle to each other. I was awe-struck, out of breath, caught between these two immensities. The very act of looking at an old painting can be so strange. It is an activity that is often bound up with class identity or social aspiration. It can sometimes feel like a diverting, or irritating, stroll among white people’s ancestors. It can also often be wonderful, giving the viewer a chance to be blessed by a stranger’s ingenuity or insight. But rarely, something even better happens: A painting made by someone in a distant country hundreds of years ago, an artist’s careful attention and turbulent experience sedimented onto a stretched canvas, leaps out of the past to call you — to call you — to attention in the present, to drive you to confusion by drawing from you both a sense of alarm and a feeling of consolation, to bring you to an awareness of your own self in the act of experiencing something that is well beyond the grasp of language, something that you wouldn’t wish to live without.

He was a murderer, a slaveholder, a terror and a pest. But I don’t go to Caravaggio to be reminded of how good people are and certainly not because of how good he was. To the contrary: I seek him out for a certain kind of otherwise unbearable knowledge. Here was an artist who depicted fruit in its ripeness and at the moment it had begun to rot, an artist who painted flesh at its most delicately seductive and most grievously injured. When he showed suffering, he showed it so startlingly well because he was on both sides of it: He meted it out to others and received it in his own body. Caravaggio is long dead, as are his victims. What remains is the work, and I don’t have to love him to know that I need to know what he knows, the knowledge that hums, centuries later, on the surface of his paintings, knowledge of all the pain, loneliness, beauty, fear and awful vulnerability our bodies have in common.

The Trayvon Generation (Elizabeth Alexander, The New Yorker)

In this essay published in June, amid a summer of protest and global uprising, poet and scholar Elizabeth Alexander writes about raising two Black sons who are now in their early 20s, and how Black creativity and communal expression emerge in response to the racism, police violence, and trauma inflicted on Black communities. In reflections on visual and musical artists, like Kendrick Lamar, whose work is both “joyful and defiant,” Alexander asks: “What does it mean for a black boy to fly, to dream of flying and transcending?” What does it mean for a Black body to dance, to move in protest and joy, in the face of racist violence? Alexander’s words are urgent and powerful, expressing love and rage and hope.

What does it mean to be able to bring together the naturalistic and the visionary, to imagine community as capable of reanimating even its most hopeless and anesthetized members? What does it mean for a presumably murdered black body to come to life in his community in a dance idiom that is uniquely part of black culture and youth culture, all of that power channelled into a lifting?

A sibling to Joseph’s work is Hiro Murai’s video for Flying Lotus’s “Never Catch Me.” It opens at a funeral for two children, a black boy and girl, who lie heartbreak-beautiful in their open caskets. Their community grieves inconsolably in the church. The scene is one of profound mourning.

And then the children open their eyes and climb out of their caskets. They dance explosively in front of the pulpit before running down the aisle and out of the church. The mourners cannot see this resurrection, for it is a fantasia. The kids dance another dance of black L.A., the force of black bodily creativity, that expressive life source born of violence and violation that have upturned the world for generations. The resurrected babies dance with a pumping force. But the community’s grief is unmitigated, because, once again, this is a dreamscape. The children spring out into the light and climb into a car—no, it is a hearse—and, smiling with the joy of mischievous escapees, drive away. Kids are not allowed to drive; kids are not allowed to die.

The Ghost Hunter (Leah Sottile, The Atavist Magazine)

In this intriguing tale, Leah Sottile brings to life a 17th-century shipwreck and an intensely curious treasure hunter who devotes years and years to uncovering its history. In 1694, a Manila galleon, the Santo Cristo de Burgos, wrecked off the coast of Oregon, near the foot of Neahkahnie mountain. For more than 150 years, treasure seekers have searched and dug for lost treasures from this galleon, said to transport valuable cargo and exotic goods across the Pacific from the Philippines to Mexico. “For generations, many Oregonians had indulged that Goonie side of themselves, allowing every single bit of wax and porcelain to restart the song of buried riches,” writes Sottile. While the idea of treasure is tantalizing, Sottile turns to another mystery: Who were the men on this ship? Who was their captain? Her questions lead her to Cameron La Follette, whose extensive research and work with faraway academics and archivists patch together the legendary galleon’s voyage and demise. LaFollette’s deep respect for the forgotten people on the Santo Cristo sets her apart from others obsessed with it, while Sottile’s careful portrait of LaFollette as a person “driven by a sense of humanity” makes for a beautifully weaved story of quirky history.

Every time González got back to her, La Follette had new questions. They went back and forth like this for a few years—new requests, new reports; new reports, new requests. Between 2015 and 2017, La Follette spent more than $10,000 of her own money paying González, other archivists, and translators in Spain, Mexico City, and Manila. “I couldn’t get a new garage door. I couldn’t get glasses that actually worked very well,” La Follette said. “I was looking at things blurry in the distance and was like, I really gotta get glasses, but it’s gonna cost $800, and I have to pay Esther’s bill.” Just like Ed Fire, La Follette couldn’t rest until she reached the bottom of her curiosity.

Eventually, González unearthed a partial cargo manifest buried deep in the archives, the best evidence yet that the Santo Cristo had, in fact, been packed with treasure: fine bedsheets embroidered with flowers, ivory sculptures of the infant Christ and saints that would be placed in New World churches, gold paper fans, delicate lace. And wax for candles.

TikTok and the Evolution of Digital Blackface (Jason Parham, Wired)

TikTok’s mission is “to inspire creativity and bring joy,” and in the beginning, for many people, it was all about fun. But Black creators on the app, like musician Brianna Blackmon, have reported instances of racism, harassment, and censorship. Jason Parham digs around, talks to nearly 30 Black creators, and learns that these problems run deep. “Blackness is a proven attention getter,” writes Parham. “Its adoption is racism, custom-fit.” In this incisive, thought-provoking piece, Parham examines a disturbing form of content production on the platform that “suggests a twisted love of Black culture through caricature,” posted primarily by young white women and white gay men. The fundamental elements of TikTok — the borrowing, remixing, and repackaging of content as one’s own — make it easy to blur the lines between flattery and mockery and theft. Is this content a new kind of collaborative performance art — or modern minstrelsy? It’s a fascinating read for understanding the dynamic, often strange content community on TikTok, the culture of Generation Z, and the appropriation of Black expression.

Wearing a mask has long been part of the social internet. The web has operated like a Party City costume shop since dotcom-era chat rooms made cool the idea of inhabiting made-up identities and hiding behind usernames. These personas could be intensely liberating, allowing people to explore hidden ideas or sexualities, or simply enjoy a carnivalesque permissiveness to say or do something outrageous. It’s all just a joke. For clout. For show.

But the mask of Blackness cannot be worn without consequences. It can’t be worn as a joke without reaching into some deep cultural and historical ugliness, without opening a wound of abuse and humiliation.

What sours this creative repackaging, mutates the joy into hatefulness, is when the content is estranged from its original context. The way someone or something can so quickly and easily be warped, diluted, recast as something other. The way one’s culture can be stolen and made monstrous, made meaningless. “TikTok all but eradicates traditional norms about cultural ownership,” the critic Jon Caramanica has written. If you spend a long enough time on the app, as I did over the past few months in lockdown reporting this story, you begin to see it as a prism through which to better understand yourself and the world around you—what draws you in, what makes you laugh, what repels you. There were moments when, scrolling through TikTok, I began to look upon myself not as I am but as blurred projections of a fractured self.

What If Friendship, Not Marriage, Was at the Center of Life? (Rhaina Cohen, The Atlantic)

What constitutes a “real” partnership? Why are marriages and other monogamous romantic relationships still generally viewed as the nucleus of one’s life? Rhaina Cohen examines friendships throughout history, from the intimate same-sex friendships of the 18th to early 20th centuries to today’s platonic partnerships. We’re introduced to Kami West and Kate Tillotson, two women who bonded in Marine Corps boot camp and have since built a deep and complex friendship, one that involves child care and emotional and social support. There’s also John Carroll and Joe Rivera, platonic partners who met at a gay bar, who have similarly broken free from the confines of traditional thinking. The idea here is that it’s impossible to expect a single person to satisfy all of one’s needs, and the people Cohen describes have custom-designed partnerships that work for them. They “can be models for how we as a society might expand our conceptions of intimacy and care,” especially now, in a pandemic that has forced us to reimagine our lives and support networks.

People expect to pile emotional support, sexual satisfaction, shared hobbies, intellectual stimulation, and harmonious co-parenting all into the same cart. Carroll, 52, thinks this is an impossible ask; experts share his concern. “When we channel all our intimate needs into one person,” the psychotherapist Esther Perel writes, “we actually stand to make the relationship more vulnerable.”

In many ways, Americans are already redefining what loving and living can look like. Just in the past several months, experts and public intellectuals from disparate ideological persuasions have encouraged heterosexual couples to look to the queer and immigrant communities for healthy models of marriage and family. The coronavirus pandemic, by underscoring human vulnerability and interdependence, has inspired people to imagine networks of care beyond the nuclear family. Polyamory and asexuality, both of which push back against the notion that a monogamous sexual relationship is the key to a fulfilling adult life, are rapidly gaining visibility. Expanding the possible roles that friends can play in one another’s lives could be the next frontier.

Willy Staley’s razor-sharp critique explores television’s depiction of New York City these days, commenting specifically on High Maintenance, Master of None, and Russian Doll. While critics have praised High Maintenance for its accurate representation of the city, Staley writes that its reality, as well as the worlds in the other two Netflix shows, ignore economic inequalities and class differences between characters. Instead, New York City on screen is an idealized composite of the experiences of young, creative-class New Yorkers and Brooklyn transplants: a fantasyland where strangers from all walks of life connect. It’s no longer a melting pot, writes Staley, but some kind of hot tub.

On High Maintenance:

The show is brilliant at sending up the anxieties and pathologies of the city’s yuppies, but characters outside this circle are often made relatable to HBO’s audience by being supplied with some quirk, hidden talent or non­-normative sexuality. In this way, the show depends on its audience’s prejudices in order to undercut them.

On Russian Doll:

The actual, transactional quasi friendships that New Yorkers have with their bodega guys are plenty interesting. Like a priest, a bodega guy gets to know the shameful weaknesses of his regulars, who must assume on some level that he’s not secretly writing their stories in his own head. His perspective would be an interesting one to get to know, but in “Russian Doll,” what’s curious about this relationship is rendered null with a couple of lines of dialogue. In trying to counteract harmful stereotypes, the show has succeeded in doing something altogether stranger: erasing diversity through the act of depicting it. By making Farran an aspirant to the same sort of success the show’s writers value, by making him a guy who thinks working at a cannery is inherently absurd, something you’d put in a novel, “Russian Doll” suggests that everyone in this city, at the end of the day, is ultimately the same, sharing identical aesthetic and professional aspirations, and we’d know that if we only paid closer attention.

Between Russell Simmons and The World and Oprah (Kevin Powell, Utne Reader)

Kevin Powell’s unconventional profile of Def Jam Recordings co-founder Russell Simmons, the “godfather of hip-hop,” is also a deep introspection on being a Black man in America, power in the time of #MeToo, and the culture of misogyny and violence in the music industry. “I struggled mightily, through the 1990s, through the heyday of my years at Vibe, as I participated in a culture that I knew was loaded with disgusting examples of manhood,” writes Powell. To date, 20 women have come forward to accuse Simmons of sexual assault, including rape; since 2018 he has reportedly lived in Bali to protect himself from prosecution, as Indonesia has no extradition treaty with the U.S. Powell also examines Oprah Winfrey’s withdrawal as executive producer from the On the Record documentary about Simmons, ultimately distancing herself from the Black women who have accused him.

HBO has purchased On The Record post-Sundance, and you will have to decide for yourself what all this is, was, and could be. But if you watch this film the way I watched it, you wonder how and why Oprah Winfrey would walk away, searching for the real reason, and how and why she could separate herself from these Black women and this film, which is like separating herself from herself. Only Oprah knows the whole truth, and perhaps Russell Simmons, godfather of hip-hop, does too—

And, honestly, this has been the most difficult piece I have ever written in my life. My emotions are bleeding, I have had painfully sleepless nights, as this story has dragged on, and on, and on. As a Black man, I do not ever want to see another Black man go down in a world already seemingly designed for us to fall. But by the same token I do not want to see Black women—or any women of any background—sacrificed just to spare a Black man—or any man of any background—accused of wrongdoing.

This hurts me from all sides, every part of it. I have been a combination of angry and sad, because of the very real and very vivid stories of the many women who’ve come forth, and because Russell Simmons had been a hero of mine, a hero for many of us boys in the ‘hood.

When he made it, we made it. When he dreamed big, we dreamed big. He was us and we were him. I could not have imagined these kinds of allegations against him when I first saw him in person at some New York City event in the early 1990s, when I just stared, because there he was, and I was too timid to greet him. I just stared, hoping whatever magic he had rubbed off on me, a poor boy from the ghetto. Nor could I have imagined, all these years later, that he would be a fallen hero, desperately trying to prove his innocence, thanking me just for listening to him, me, the writer who had found his voice, long ago, because of the culture—our culture—Russell Simmons helped to bring to the entire world.

Wonder Women (Soraya Roberts, Hazlitt)

Was 2020 really the year of the female superhero? Looking back on films like Catwoman, Elektra, and Captain Marvel, and considering this year’s movies like Birds of Prey, the soon-to-be-released Wonder Woman 1984, and the upcoming Black Widow, on the surface you’d think Hollywood finally gets it. But Soraya Roberts argues that today’s female superheroes still operate within a world ruled by white men. Having spoken in May to the original Supergirl herself — Helen Slater, who starred in the 1984 film — Roberts explores the legacy of female superhero films and asks what has changed in the past 30+ years, and what has unfortunately stayed the same.

Catwoman paws at feminism—“Catwomen are not contained by the rules of society,” Berry’s character says—but this soft-core fantasy is still bound by the limits of the male imagination. The film is very much an expression of a popular brand of feminism from the early aughts, just as Elektra would be a year later (another spin-off afterthought rush job, this time from Marvel’s Daredevil, with Jennifer Garner playing a bustier-clad assassin). While real activism could be found that year in Washington’s birth control march and in personal blogs by a diverse array of young women, popular culture preferred a more photogenic brand of lipstick feminism. Practitioners performed their sexuality as a means of subverting male strictures on women’s bodies, except that their behaviour happened to play into the very male gaze it claimed to be challenging. As Ariel Levy writes in Female Chauvinist Pigs: Women and the Rise of Raunch Culture: “Proving that you are hot, worthy of lust, and—necessarily—that you seek to provoke lust is still exclusively women’s work.” Has a male superhero ever been asked, like Elektra, if he has time to get laid? Female superheroes may be immortal, but the Gods remain men.

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Cheri has been an editor at Longreads since 2014. She's currently based in the San Francisco Bay Area.