During this time, Alain Locke coined the idea of the "New Negro", which was focused on creating progressive and uplifting images of blacks within society.

[2] The synthesis of black representation and visual culture drove the basis of Motley's work as "a means of affirming racial respect and race pride.

He describes his grandmother's surprisingly positive recollections of her life as a slave in his oral history on file with the Smithsonian Archive of American Art.

[5] During World War I, he accompanied his father on many railroad trips that took him all across the country, to destinations including San Francisco, Los Angeles, Hoboken, Atlanta and Philadelphia.

In his oral history interview with Dennis Barrie working for the Smithsonian Archive of American Art, Motley related this encounter with a streetcar conductor in Atlanta, Georgia: I wasn't supposed to go to the front.

During his time at the Art Institute, Motley was mentored by painters Karl Buehr and John W. Norton,[6] and he did well enough to prompt his father's friend to pay his tuition.

[5] He found in the artwork there a formal sophistication and maturity that could give depth to his own work, particularly in the Dutch painters and the genre paintings of Delacroix, Hals, and Rembrandt.

Motley experienced success early in his career; in 1927 his piece Mending Socks was voted the most popular painting at the Newark Museum in New Jersey.

During the 1930s, Motley was employed by the federal Works Progress Administration to depict scenes from African-American history in a series of murals, some of which can be found at Nichols Middle School in Evanston, Illinois.

After his wife's death in 1948 and difficult financial times, Motley was forced to seek work painting shower curtains for the Styletone Corporation.

By asserting the individuality of African Americans in portraiture, Motley essentially demonstrated Blackness as being "worthy of formal portrayal.

Motley spoke to a wide audience of both whites and Blacks in his portraits, aiming to educate them on the politics of skin tone, if in different ways.

"[10] This is consistent with Motley's aims of portraying an absolutely accurate and transparent representation of African Americans; his commitment to differentiating between skin types shows his meticulous efforts to specify even the slightest differences between individuals.

In an interview with the Smithsonian Institution, Motley explained his motives and the difficulty behind painting the different skin tones of African Americans: They're not all the same color, they're not all black, they're not all, as they used to say years ago, high yellow, they're not all brown.

It could be interpreted that through this differentiating, Motley is asking white viewers not to lump all African Americans into the same category or stereotype, but to get to know each of them as individuals before making any judgments.

During this time, Alain Locke coined the idea of the "New Negro," which was very focused on creating progressive and uplifting images of Blacks within society.

Source:[18] In his paintings of jazz culture, Motley often depicted Chicago's Bronzeville neighborhood, which offered a safe haven for blacks migrating from the South.

The excitement in the painting is palpable: one can observe a woman in a white dress throwing her hands up to the sound of the music, a couple embracing—hand in hand—in the back of the cabaret, the lively pianist watching the dancers.

She wears a black velvet dress with red satin trim, a dark brown hat and a small gold chain with a pendant.

Motley's use of physicality and objecthood in this portrait demonstrates conformity to white aesthetic ideals, and shows how these artistic aspects have very realistic historical implications.

It appears that the message Motley is sending to his white audience is that even though the octoroon woman is part African American, she clearly does not fit the stereotype of being poor and uneducated.

Thus, this portrait speaks to the social implications of racial identity by distinguishing the "mulatto" from the upper echelons of black society that was reserved for "octoroons.

Source:[25] During this period, Motley developed a reusable and recognizable language in his artwork, which included contrasting light and dark colors, skewed perspectives, strong patterns and the dominance of a single hue.

Nightlife, in the collection of the Art Institute of Chicago, depicts a bustling night club with people dancing in the background, sitting at tables on the right and drinking at a bar on the left.

[26] The entire image is flushed with a burgundy light that emanates from the floor and walls, creating a warm, rich atmosphere for the club-goers.

In Nightlife, the club patrons appear to have forgotten racism and are making the most of life by having a pleasurable night out listening and dancing to jazz music.

In an interview with The Whitney Museum, art historian Davarian Baldwin argues that, much like in Black Belt and Bronzeville at Night, Motley renders in this painting the nightlife activities that could be observed on Chicago's The Stroll.

[27] Langston Hughes described this entertainment, leisure, and business district in Chicago’s Black Belt community after the First World War as a street that was "full of workers and gamblers, prostitutes and pimps, church folks and sinners."

The Stroll's variety is present in the painting, from the figure on the soapbox labeled "Jesus Saves," to the suggestive couple in the foreground, to the nuclear family observing the scene from their porch in the background.

Motley married his high school sweetheart Edith Granzo in 1924, whose German immigrant parents were opposed to their interracial relationship and disowned her for her marriage.