The Lovelies of John Alan Maxwell begins in 1985, when young Doug McDaniel leaves home to spend the summer with his grandmother, Gladys Maxwell McDaniel, before leaving for college. He learns of the death of her brother, his great uncle, the year before. Kept from knowing much about this uncle from his domineering family, the young man begins learning stories about his uncle from his grandmother and her sister Elizabeth as they attempt to settle their brother's estate, which consists of hundreds of paintings and thousands of sketches left in Maxwell's small Johnson City studio apartment.

A Knoxville stock broker with a large cocaine addiction is helping Gladys and Elizabeth get the art into a permanent, public museum, but Doug and Gladys don't trust him. Gladys dies suddenly, only five days after Doug leaves for college, and the art is traded suspiciously, never making it to a public museum.

Doug continues to study the work of his uncle, unsatisfied with the lack of details his grandmother and her sister had shared with him. He is particularly drawn to a painting of an unknown young woman. He begins to interview people who had known his uncle, including the Associated Press reporter Willa Gray Martin Pierce, not knowing that Pierce's son-in-law was then Vice President George H. W. Bush.

Over a span of 25 years, McDaniel becomes obsessed with his uncle's life and work, and discovers many works that no one in the family ever acknowledged: works for John Steinbeck, Pearl S. Buck, Ernest Hemingway, Sir Arthur Conan Doyle, and countless other important 20th century novelists and poets. He learns details of his uncle's life, including the influences of Maxwell's Confederate grandfather wounded in the Civil War. McDaniel confirms Maxwell's studies at the Corcoran School of Art in Washington in 1921 and the Art Students League in New York under such important Ashcan School artists George Bellows and George Luks, and also Frank Vincent Dumond, who taught Georgia O'Keefe and Norman Rockwell. Maxwell's role in the Society of Illustrators, the Dutch Treat Club, and his beloved studio at the famous Tenth Street Studio, known as Old 51, at 51 West Tenth Street in Greenwich Village, where Maxwell becomes known for telling ghost stories about old friends, from artist John LaFarge to the Lebanese poet and artist Kahlil Gibran.

Relationships in the bohemian culture of 1920s and 1930s Greenwich Village are explored, as well as Maxwell's commitment to romantic realist art that predated the abstract expressionism of the 1940s, as well as his love of the human form, expressed through Maxwell's prolific illustrations of the grotesque and erotic.

In 1948, Esquire Magazine compared John Alan Maxwell to William Faulkner and Thomas Wolfe as one of the many talents of the Modern South. This film is a tribute to the life and work of countless 20th century illustrators like Maxwell who labored tirelessly through the Great Depression and World War II, fearlessly committed to their art and their work.