1. Vincent Van Gough
    Only sold one painting in his life. When he couldn't afford canvases (often) he painted on top of other paintings or on his walls
  2. Emily Dickenson
    Only published seven (I believe) of her thousands of poems during her life, and those were altered by publishers. A notorious recluse
  3. Vivian Maier
    Prolific photographer moonlighting as a nanny. Photographs only found after death
  4. Henry David Thoreau
    Largely (critically) considered fringe/outsider in his time, although he was beloved and admired by writers like Emerson and Robert Frost
  5. Otis Redding
    Did find success, but not nearly enough. His was the first posthumous song to hit #1 on the billboard top 100 and R&B charts with (Sittin' on) The Dock of The bay
  6. Franz Kafka
    Read once that his primary source of income was working as an insurance agent. Asked that his works be burned upon his death
  7. John Kennedy Toole
    Tried to publish A Confederacy of Dunces for years. Gave up. Committed suicide. The novel, published posthumously, won the Pulitzer Prize.
    Suggested by @ChrisK
  8. Nick Drake
    Folk singer who died too young.
    Suggested by @MatthewAlmont
  9. Edgar Allan Poe
    During his life Poe made a meager living off of his writings, sometimes only making a few dollars per publication.
    Suggested by @finesse
  10. Zora Neale Hurston
    Brilliant and renowned author who died in poverty and obscurity in an unmarked grave
    Suggested by @Zeealist