The 100 best paintings in New York: 20-11

Where can I see it?: The LGBT Center

Before succumbing to AIDS in 1990 when he was 31, Keith Haring painted this mural on the walls of the men’s bathroom at the LGBT Center. In his signature black linear style, replete with curlicues and radiant lines, he celebrated gay male sexuality in graphic, cartoony detail. Lines don’t adhere to fixed roles, as the insides of bodies become the outside in a frenzy of activity. Made during the height of the AIDS crisis, the fear surrounding the disease is supplanted with defiant joy.—Jennifer Coates

Photograph: Travis Mark / Artwork: Courtesy the NYC LGBT Community Center and copyright Keith Haring Foundation

Where can I see it?: The Metropolitan Museum of Art

It’s a comic-strip–like religious narrative. In the central panel, the Virgin sits reading, as yet unaware of the angel Gabriel, who has just popped into being. A miniature Christ child speeds toward her, carried on beams of light. And next door, Joseph busies himself making mousetraps.—Anne Doran

Photograph: Courtesy the Metropolitan Museum of Art

Where can I see it?: The Metropolitan Museum of Art

In the late 1960s, Guston abandoned the Ab Ex that had brought him renown and began painting strange cartoonish images, inspired in part by R. Crumb. The big-eyed being in the initially derided Stationary Figure smokes in bed beneath a bare bulb and a window of black sky. The humor, absurdity and deceptively childlike rendering only add to the overriding sense of melancholy.—Joseph Wolin

Photograph: Courtesy Estate of Philip Guston

Where can I see it?: Brooklyn Museum

Wealthy, eccentric and bohemian spinsters, the fabulous Stettheimer sisters hosted midtown salons that attracted the likes of fellow artists Marcel Duchamp and Georgia O’Keeffe. Florine herself painted fanciful scenes like Heat, which depicts the sisters languidly wilting at a birthday party for their mother. Quirky details, such as a kitten clawing at the artist’s wrist in the lower right or what appears to be the Brooklyn Bridge in the upper left, combine with a sure sense of the decorative to reveal a pioneering female artist blazing her own path.—Joseph Wolin

Artwork: Courtesy Brooklyn Museum

Where can I see it?: Museum of Modern Art

This one has the makings of a great horror movie: raw meat, sides of beef that appear crucified, guillotine-like window shades and a mysterious man in a black suit who seems little more than a set of teeth rimmed in crimson. The bilious pink palette doesn’t make things lighter either. Yet coming hard on the heels of the Blitz, Auschwitz and Hiroshima, this nightmarish image by the British artist echoes with lived terror and existential dread.—Joseph Wolin

Photograph: Courtesy the Museum of Modern Art

Where can I see it?: Museum of Modern Art

Ensor lived all of his life in the seaside resort town of Ostend, Belgium, where his family had a business selling souvenirs and masks—and he often used the latter in his paintings to convey the psychological states and satirize the politics, religion and culture of modern Belgian society. Here a foppish specimen is menaced by masked figures even more bizarre than itself.—Anne Doran

Photograph: Courtesy the Museum of Modern Art

Where can I see it?: Museum of Modern Art

Orange Car Crash, a repeating image of a ghastly road accident that was originally a newspaper photo, is a particularly striking example of Warhol’s deeply dark side. Part of an overall series focusing on death and disaster, the painting expresses his fascination with tabloids and smut journalism. His use of repeatedly silkscreened imagery on a half-empty diptych puts a formal distance between viewer and calamity, turning exploitation into abstraction.—Howard Halle

Photograph: Courtesy the Museum of Modern Art

Where can I see it?: Museum of Modern Art

Measuring 10 by 86 feet, F-111 is less of a painting than it is a dioramic distillation of American life at the height of the Cold War. It would have fit right in at Times Square, back before the advent of giant digital screens. The space where F-111 debuted was relatively small. It was an environment that wrapped viewers in images linking consumer culture to the military-industrial complex, with glimpses of a tire, a cake and a little girl under a massive hair dryer, all laid over the titular subject: a super expensive, swing-wing bomber.—Howard Halle

Photograph: Courtesy the Museum of Modern Art

Where can I see it?: The Metropolitan Museum of Art

Still having her red-carpet moment after 130 years, the Parisian socialite, as painted by American expat Sargent, serves us Gilded Age glamour with a profile that just won’t quit. Sargent created this glorious life-size portrait to impress the European public. It didn’t. Despite its virtuosity, the bare shoulders and plunging décolletage proved scandalous, so Sargent put it away for three decades; when he sold it to the Met, he asked that the sitter be given a pseudonym.—Joseph Wolin

Photograph: Courtesy the Metropolitan Museum of Art

Where can I see it?: Museum of Modern Art

For some half a century, Ron Gorchov’s art has flown in the face of his contemporaries, most of whom insist on working with conventional two-dimensional canvases. Instead, Comet, like many of Gorchov’s sculpture-paintings, takes a vaguely saddle-like shape. While the piece’s name might evoke space and the future (we recently landed a spacecraft on a comet), it also brings to mind something ancient, something coded in our DNA from humanity’s earliest days.—Drew Toal

Photograph: Courtesy the Museum of Modern Art