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1927- Completed his first oil painting after three years of work.  "One day I decided to get some oil paint and I started the picture that was in my mind. 'End of the War:  Starting Home.'"4

1931- Completed Shell Holes and Observation Balloon, one of three oil paintings of war scenes.

1934- Painted for short periods at a time since his arm and shoulder were still sore.

1937- Entered two paintings in the West Chester County Art Association's annual invitation show.  N.C. Wyeth, the famous illustrator, commented on the fine quality of Pippin's paintings and persuaded Dr. Christian Brinton, President of the association, to give Pippin a one-man show.
Ten paintings and seven burnt-wood panels were exhibited at the West Chester Community Center in June.  The exhibition was a success, resulting in the sale of several art works and Pippin's introduction to Main Line Society.

1938- Museum of Modern Art, New York held the exhibition, "Masters of Popular Painting," which included four Pippins selected by Holger Cahill from the 1937 one-man show.

1939- Robert Carlen of Robert Carlen Galleries, Philadelphia, became Pippin's art dealer in December.

1940- Robert Carlen Galleries, Philadelphia, exhibited twenty-three oil paintings in the "Horace Pippin Exhibition," which included a catalogue with an introduction by Albert C. Barnes.  The Barnes Foundation had previously purchased three paintings and Barnes had invited Pippin to visit his collection in Merion, Pennsylvania.  Pippin attended lectures at the Foundation for several weeks, where he was briefly exposed to the modern painting of C├ęzanne, Matisse, Picasso, Renoir and works by Old Masters.5

1941- Produced his last eight burnt-wood panels.
One-man shows were held at the Robert Carlen Galleries, the Arts Club of Chicago, and the Bignou Gallery, New York; including Pippin's first still-life paintings, Roses with Red Chair and Warped Table.

1942- One-man show at the San Francisco Museum of Art.
Painted three pictures of John Brown, the White Abolitionist.  Pippin, whose grandparents were slaves and whose grandmother witnessed the hanging of John Brown, saw him as a legendary folk hero.  In John Brown Going to His Hanging, Pippin recalled the scene he so often heard described.
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