In 1913, 31-year-old Edward Hopper sold his first painting at the legendary Amory Show, an exhibit hosted by the Association of American Painters and Sculptors that featured around 1,250 paintings, sculptures, and decorative works by more than 300 artists. Entitled “Sailing,” the simple painting portrays a lone sailboat on calm waters, its strong sails boosted by wind, stretching in to the blue sky amidst the muted color palettes that would later become Hopper’s trademark.

However, the Edward Hopper we know and love—the American artist of searing honesty, painful realism, and subtle despair—was still 10 years from the making. In fact, the Edward Hopper of the Amory Show was an indisputable failure. Success, Hopper would find, was an allusive creature that dodged and evaded his every grasp and slipped away to the nautical reaches of his early work.

All he needed, though, was a woman.

Born July 22, 1882 in Nyack, NY, Hopper showed an early talent in drawing. Though he grew up in a modest middle-class environment, Hopper’s parents were extraordinarily supportive of their son, offering encouragement and material aid, which included a wide range of painting materials such as charcoal, watercolor, and oil.

Though Hopper entered a correspondence school in 1899, following parental advice to seek a more profitable, commercial job, Hopper ultimately studied at the prestigious New York Institute of Art and Design for six years. Then, in 1905, Hopper landed an illustrating job for an advertising agency, designing covers for trade magazines. Hopper despised the occupation.

Notwithstanding his venomous attitude towards illustrating, Hopper would stay in the business for more than 20 years, as his painting career attracted little interest. Not that Hopper was not trying: he traveled to Europe on three separate occasions, absorbing the emerging styles of art (mainly in Paris) such as Impressionism, while increasing his education in classics, such as Rembrandt.

“It’s hard for me to decide what I want to paint,” Hopper said of his creative process at the time. “I go for months without finding it sometimes. It comes slowly.”

Hopper rented a studio in New York, but he was forced to partake in door-to-door appeals to endorse his work. In the meantime, he continued illustrating, this time working for a movie production company and designing movie posters. Walter Tittle, a fellow illustrator who knew Hopper at the time, said Hopper suffered “from long periods of unconquerable inertia, sitting for days at a time before his easel in helpless unhappiness, unable to raise a hand to break the spell.”

For a brief time, Hopper turned to etching, producing about 70 works that received some acclaim. Things, however, were finally about to turn for the poor, frustrated Hopper. All he needed was a woman.

Gloucester, MA served as a site of inspiration for Hopper. He had previously traveled to the town in 1912, where he painted his first lighthouse painting, a staple subject of his early work. A later trip, this one in 1923, reunited Hopper with a one Josephine Nivison, an artist and former student of Robert Henri, one of Hopper’s teachers at the New York Institute of Art and Design.

They married a year later and remained lifelong partners. Following their marriage, Hopper’s career began accumulating momentum. As the manager of his affairs, Josephine abandoned her own artistic aspirations for those of her husband’s, organizing six of Hopper’s Gloucester paintings at a 1923 exhibit at the Brooklyn Museum. The museum purchased one of the paintings, “The Mansard Roof,” for $100, and Hopper later sold all of his watercolors at a personal exhibit a year later.

Finally, at 41, after years of painful illustrations, personal doubt, and sacrifice, Hopper’s career as a painter solidified. His early successes, however, did not feature the lonely, secluded human subjects of his latter-day work, but rather, the lighthouses and homes of the sunny New England villages he often visited.

Despite this fact, Hopper’s stark portrayals of seaside living are stunning, boasting realistic colors, impressionistic brush work, and some of the more dramatic uses of shadow this side of film noir, a genre Hopper indelibly influenced; furthermore, the works served as inspiration for a number of Hollywood films, most notably Alfred Hitchcock’s Psycho, which based the ominous house on the hill of Norman Bates on Hopper’s Gloucester work.

The true irony of Hopper’s sudden success, though, was that it came from a wife of most unlikely compatibility. Hopper, standing an imposing six feet six inches, was quiet, focused, and uncomfortably intense, with his long, interminable silences and bouts of observation that often rendered his peers uncomfortable.

Josephine, on the other hand, was short, round, and jolly, routinely dominating the interviews in which the couple would partake and regularly clashing with her husband. Hopper would often eschew personal confrontation for subtle wit, leaving Josephine ironic, sometimes bitter drawings and notes around the house (or even paintings, such as this work, “Four Lane Road”). Differences aside, Josephine was the main key to Hopper’s success and his muse, serving as the model for the numerous female subjects of his paintings (a fine example being this painting, “Office at Night”).

Hopper would continue to work as a painter for the next four decades, shifting his focus from buildings to human subjects while commanding prodigious fees for his products. In 1931, for example, with the Great Depression in full swing, Hopper sold 30-some paintings, fetching thousands of dollars for each one.

“Nighthawks,” Hopper’s 1942 painting, is a masterpiece of American art, and the impeccable structure of the work justifies its rather overwhelming reputation.

On first glance, the painting seems basic, even comical. An isolated diner in an unmarked city. Three customers. One employee. “Phillies” printed in basic yellow across the diner’s outside. But such was the genius of Hopper: his uncanny ability to transmit thousands of words and emotions with the simplest of images.

Produced in the twilight of Pearl Harbor, Hopper set the painting in the most American of all images: the diner. The characters, dazed and stunned at their loss of innocence, sit blankly, staring off into the abyss of international maturity. All the while, the bright, white light of the diner is swallowed whole by the ominous darkness of the city. Hopper properly encapsulated an entire nation’s grief into one painting, and every time I visit the Art Institute of Chicago, where the painting resides, I am moved by its honesty.

“Nighthawks” secured Hopper’s status as a household name, and the painting continues to introduce new generations to Hopper’s work.

In February of 2008, I visited the Art Institute of Chicago’s special “Hopper Exhibit,” a blowout show that included the earliest of Hopper’s sketches and etchings to his last completed painting, “Two Comedians.” As I walked through the exhibit, though, and viewed masterpiece after masterpiece, it became patently clear that Edward Hopper was a visionary far beyond “Nighthawks.” While that masterpiece serves as an indelible introduction to Hopper’s work, the scope of the piece—the fact that it specifically targets post-Pearl Harbor America—actually limits, in my mind, the true cusp of Hopper’s vision, which was a specific brand of America permeated in sadness.

Works such as “Automat,” “Chop Suey,” “Office in a Small City,” “Room in New York,” and “Pennsylvania Coal Town,” all concerned themselves with the fear of modernity and the loss of intimacy, how all of our various technological advances and economic, capitalistic gains seem to advance our human connection further and further apart. This quality, in today’s terms of the Internet and text messaging, makes Hopper seem like a prophet.

A second quality that works with this disconnect is an uncomfortable sexuality, best seen in “Morning in a City.” One of a number of Hopper’s works that feature nude women, the brand of nudity Hopper employs is entirely devoid of eroticism. The pink, white, full-fleshed bodies bare little resemblance to the movie stars of the era; instead, Hopper’s use of nudity further communicates this disconnect, emphasizing restrained, desperate women who desire affection…so much so, they’ll stare out of apartment windows in the nude.

My absolute favorite Hopper, though, is “Western Motel,” a 1957 work. A homely woman, dressed in a simple purple outfit, sits on a bed, a puzzled, empty expression on her face, which looks directly at the viewer. Suitcases lay by the bedside, a shirt rests on a chair, and a car can be seen through the motel room’s window. Hopper certainly produced better paintings with stronger color, composition, and importance, but the reason that “Western Motel” always, without fail, grabs my attention is its narrative.

All of Hopper’s paintings, especially his later work, emphasize the narrative, the snapshot quality of an artist capturing the subject’s actions. Hopper’s narratives, however, are brilliantly incomplete and ambiguous: is the woman in “Western Motel” traveling with her husband? Does a faulty marriage explain her blank look? Or, perhaps, her look is not blank, but bold and of pride, of strength? Maybe she left her husband? Maybe she is setting off on a new course in life, proud and unapologetic in her decision?

Hopper intentionally leaves these questions unanswered. He forces us to answer. He demands it. He shows us, as we stare at the representations of our own sorrow, what it means to be human.