He numbered among his friends some of the most famous individuals of the early 20th century, including Salvador Dalí, Ernest Hemingway, and Henri Cartier-Bresson.

It was the first to publish works by several struggling authors who later became famous, including James Joyce, Kay Boyle, Ernest Hemingway, Hart Crane, D. H. Lawrence, and René Crevel.

He was the product of generations of blue-blood English and Dutch American families, descended from the Van Rensselaers, Schuylers, Morgans, and Grews.

Taking his studies very lightly, he thought he was going to fail, and paid a knowledgeable man who was familiar with what questions would be asked on the examinations to tutor him.

[2][11]: 2 On September 9, 1922, Crosby and Polly were married in the Municipal Building in New York City, and two days later they reboarded the RMS Aquitania and moved with her children to Paris.

They found an apartment at 12, Quai d'Orléans overlooking the Seine, on the exclusive Île Saint-Louis, and Polly donned her red bathing suit and row Crosby down the Seine in his dark business suit, formal hat, umbrella, and briefcase[14] to the Place de la Concorde, where he walked the last few blocks to the bank on Place Vendôme.

"[17] In 1924, they rented an apartment in the Faubourg St. Germain for six months from Princess Marthe Bibesco, a friend of Crosby's cousin Walter Berry, for 50,000 francs (the equivalent of $2,200, about $40,365 in today's dollars).

"[2]: 145 His inheritance, multiplied by the favorable exchange rate the American dollar enjoyed in postwar Europe, allowed them to indulge in an extravagant expatriate lifestyle.

[2]: 144 The couple became known for hosting small dinner parties from their giant bed in their palatial townhouse on Île Saint-Louis, and afterward everyone was invited to enjoy their huge bathtub together, taking advantage of iced bottles of champagne near at hand.

[2]: 132 On November 19, 1925, Crosby and Polly rented a fashionable apartment on 19, Rue de Lille, where they remained for the rest of their time in Paris.

The ground floor of the central mill tower served as a dining room, where guests sat on logs cut from the neighboring woods.

[15] Henry wrote in his journal: Mobs for luncheon—poets and painters and pederasts and divorcées and Christ knows who and there was a great signing of names on the wall at the foot of the stairs and a firing off of the cannon and bottle after bottle of red wine and Kay Boyle made fun of Hart Crane and he was angry and flung The American Caravan into the fire because it contained a story of Kay Boyle's (he forgot it had a poem of his in it) and there was a tempest of drinking and polo harra burra on the donkeys.

[25] In 1923, shortly after their arrival in Paris, Caresse introduced Crosby to her friend Constance Crowninshield Coolidge, also a Boston Brahmin, an American expatriate.

"[2]: 214–215  The three remained close friends, and on October 1, 1924, Constance married the Count Pierre de Jumilhac, although the marriage lasted only five years.

He became legendary for his seductive abilities in some social circles in Paris,[4] maintaining relationships with a variety of beautiful and doting young women.

He wrote in his diary about it later:[7] I remember two strong young men stark naked wrestling on the floor for the honor of dancing with a young girl...and I remember a mad student drinking champagne out of a skull which he had pilfered from my Library as I had pilfered it a year ago from the Catacombs...and in a corner I watched two savages making love...and beside me sitting on the floor a plump woman with bare breasts absorbed in the passion of giving milk to one of the snakes!One year, Caresse arrived topless riding a baby elephant and wearing a turquoise wig.

The motif for the ball that year was Inca, and Crosby dressed for the occasion, covering himself in red ochre and wearing nothing but a loincloth and a necklace of dead pigeons.

In 1928, as Éditions Narcisse, they printed a limited edition of 300 numbered copies of "The Fall of the House of Usher" by Edgar Allan Poe with illustrations by Alastair.

[29] They published early works of several writers before they were well known, including James Joyce's Tales Told of Shem and Shaun (which was later integrated into Finnegans Wake).

[34] Crosby and Josephine met and traveled to Detroit, where they checked into the expensive ($12 a day—about $220 today) Book-Cadillac Hotel as Mr. and Mrs Harry Crane.

[13] Crosby and Caresse made plans to see Crane again before they left for Europe on December 10 to attend the popular Broadway play Berkeley Square.

The coroner reported that Crosby's toenails were painted red, and that he had a Christian cross tattooed on the sole of one foot and a pagan icon representing the sun on the other.

[2] The New York Times front page blared, "COUPLE SHOT DEAD IN ARTISTS' HOTEL; Suicide Compact Is Indicated Between Henry Grew Crosby and Harvard Man's Wife.

She related that Crosby had told her, "the Rotch girl was pestering him; he was exasperated; she had threatened to kill herself in the lobby of the Savoy-Plaza if he didn't meet her at once.

She also established, with Jacques Porel, a side venture, Crosby Continental Editions, that published paperback books by Ernest Hemingway, William Faulkner, and Dorothy Parker, among others.

[11] The Black Sun Press produced finely crafted books in small editions, including works by, among others, D. H. Lawrence, Archibald MacLeish, James Joyce, Kay Boyle, and Hart Crane.

"I had written at length about the life of Harry Crosby, who I scarcely know," he wrote, "in order to avoid discussing the more recent death of Hart Crane, whom I know so well that I couldn't bear to write about him.

"[40][41] In 1931, Caresse also published Torchbearer, a collection of his poetry with an afterword by Ezra Pound, and Aphrodite in Flight, a 75-paragraph-long prose-poem and how-to manual for lovers that compared making love to a woman to flying planes.

[42] During 1931 and 1932, Caresse collaborated with Harry's mother Henrietta to publish letters he had written to his family while serving in France from the summer of 1917 until he returned home in 1919.

A rare volume published by the Black Sun Press of Hart Crane's book-length poem The Bridge, including photos by Walker Evans, was sold by Christie's in 2009 for US$21,250.