The Black Sun Press was an English-language press noted for publishing the early works of many modernist writers including Hart Crane, D. H. Lawrence, Archibald MacLeish, Ernest Hemingway, and Eugene Jolas. It enjoyed the greatest longevity among the several expatriate presses founded in Paris during the 1920s, publishing nearly three times as many titles as did Edward Titus under his Black Manikin Press. Its frontleaf bore their names in the form of a gold cross with the 'r' in Caresse intersecting the first 'r' in Harry's name. The second was Harry’s Sonnets for Caresse. The books were handmade, "lavishly bound, typographically impeccable" versions of unusual books that interested them, like The Fall of the House of Usher by Edgar Allan Poe with illustrations by Alastair (Baron Hans Henning Voigt). They printed a Hindu "Love Book," and letters sent to Harry’s cousin, Walter Berry, by Henry James. in expensive state-of-the art materials made by Babout. They sold their collection of Kay Boyle's short stories through Shakespeare and Company.

In 1928, Harry and Caresse changed the name of the press to the Black Sun Press in keeping with Harry's fascination with the symbolism of the sun. The press rapidly gained notice for publishing beautifully bound, typographically flawless editions of unusual books. They took exquisite care with the books they published, choosing the finest papers and inks.

Expand literary circle

Their literary tastes matured and they sought out their Parisian literary friends and offered to publish their writing. Their friends included D. H. Lawrence, for whom they published a limited edition of 50 copies of The Escaped Cock, illustrated by John Farleigh, in September 1929 (later re-published as The Man Who Died). Lawrence later wrote the introduction to Harry Crosby's volume of poetry, Chariot of the Sun.

Harry occasionally spent time with one of their authors, Ernest Hemingway, who he had met skiing, and in July 1927 they visited Pamplona for the running of the bulls. Harry often drank to excess when with Hemingway. Although Harry spoke fluent French, they socialized primarily among fellow American expatriates.

In 1928, Harry's cousin Walter Berry died, leaving a considerable collection of over 8,000 mostly rare books. In his will he left "all the rest of my books...except such books which Edith Wharton may desire to take...I give and bequeath to my cousin, Harry Grew Crosby." Harry eagerly campaigned to persuade Berry's long-time friend Edith Wharton to give him a great many of the books, and in the end she kept less than 100. Harry prized the collection at first but he became enamored of the idea of reducing the things around him. Caresse later wrote, "We had talked to a wise man in Egypt in 1928 who said, 'My wealth I measure by the things I do without,' and Harry believed the books weighed him down."

The Black Sun Press also published the poetry of Archibald MacLeish, who had like Harry overturned the normal expectations of society, rejecting a career as a lawyer with one of Boston's best law firms and lecturing at Harvard. Harry offered to publish MacLeish's long poem Einstein in a deluxe edition, and paid MacLeish US$200 for his work. They printed 150 copies which were quickly sold. In late June that year, Crane returned from the south of France to Paris. Harry noted in his journal, "Hart C. back from Marseilles where he slept with his thirty sailors and he began again to drink Cutty Sark..." Crane, a heavy drinker since his early days in New York, got drunk at the Cafe Select and fought with waiters over his tab. When the Paris police were called, he fought with them and was beaten. They arrested and jailed him, fining him 800 francs. After six days in prison at La Santé, Harry Crosby paid Crane's fine and advanced him money for the passage back to the United States The first 100 copies of Joyce's book were printed on Japanese velum and signed by the author. It was hand-set in Caslon type and included an abstract portrait of Joyce by Constantin Brâncuși, a pioneer of modernist abstract sculpture. Brâncuși's drawings of Joyce became among the most popular images of him.

During the rest of 1929, they published fourteen works by Ernest Hemingway, James Joyce, René Crevel, T. S. Eliot, and Ezra Pound among others. Caresse wrote a book of poetry, Crosses of Gold, which they published. The Crosbys also published early works by newly emerging writers including Ramon Sartoris, Julien Levy,

Beautiful books in limited editions

thumb|Cover from Transit of Venus, poetry written by Harry Crosby and published by Black Sun Press, in 1929.The books they published were "beautifully bound, hand set books." One of their most beautiful books was the Hindu Love Manual which they first found while on holiday in Damascus. They reprinted it in October 1928 in a release of only 20 copies. Bound in navy blue leather, the cover was stamped with gold to reflect the style of ancient Persian manuscripts. The inside pages were printed on handmade paper colored a distinctive shade of gray and decorated with a gold border. Each illustration in every copy was hand-colored.

In 1929, they published Harry Crosby's volume of verse, Mad Queen, which showed the influence of Surrealism and which included withering attacks on Bostonian tradition. Apart from his obsession with the sun, his writing increasingly contained references to dissolution and suicide. Josephine would inspire Crosby's next collection of poems which he dedicated to her, titled Transit of Venus. Josephine married Albert Smith Bigelow on June 21, 1929, but Harry and Josephine rekindled their affair within a few weeks. Unlike his wife Caresse, Josephine was quarrelsome and prone to fits of jealousy. Harry and Josephine went to Detroit and checked into the expensive ($12 a day) Book-Cadillac Hotel as Mr. and Mrs. Harry Crane. The party went on until nearly dawn,

On the same day, Harry Crosby wrote his final entry in his journal: