It has been posited that Halleck was in love with Drake. This presumption is not without reason; Halleck describes serving as best man at Drake's wedding:
"[Drake] has married, and, as his wife's father is rich, I imagine he will write no more. He was poor, as poets, of course, always are, and offered himself a sacrifice at the shrine of Hymen to shun the 'pains and penalties' of poverty. I officiated as groomsman, though much against my will. His wife was good natured, and loves him to distraction. He is perhaps the handsomest man in New York, - a face like an angel, a form like an Apollo; and, as I well knew that his person was the true index of his mind, I felt myself during the ceremony as committing a crime in aiding and assisting such a sacrifice.
Drake had advised Halleck to pursue becoming a nationally-known poet and to sit on "Appalachia's brow" to take in the immense power of nature and use it to inspire his imagination. A medical student, Drake died of consumption at 25 and Halleck commemorated his friend's death with a mournful poem that is considered by many as his most heartfelt, beginning "Green be the turf above thee" (1820).
Halleck then penned Fanny, his longest poem, also a satire on the literature, fashions, and politics of the time, published anonymously in December 1819. So popular was it at the time that the 50 cent edition was fetching up to $10 before a second extended edition arrived to satisfy demand.
Halleck was never a professional poet. He left school at 15 to work in his families shop in Guilford, and upon coming to New York in May 1811, he became a clerk in the New York bank of Jacob Barker, where he remained for 20 years. On May 15, 1832, Halleck became the private secretary to John Jacob Astor and was appointed by him one of the original trustees of the Astor Library of New York. He also functioned as Astor's cultural tutor, advising him on what pieces of art to purchase. The immensely wealthy--and tightfisted--Astor in his will left to Halleck an annuity of only $200, a meager sum which Astor's son William increased to $1,500. In 1849 he retired to his hometown of Guilford where he spent the rest of his life living with his older unmarried sister. He died in 1867 and is buried at Alderbrook Cemetery in Guilford.
In the mid to late 19th century, Halleck was regarded as one of America's leading poets, dubbed "the American Byron." Charles Dickens spoke very fondly of the "accomplished writer" in a January 1868 letter to William Makepeace Thackeray (as recounted in "Thackeray in the United States"). It is not clear how much of Dickens's fondness is based on Halleck's poetical ability and how much on his wit and charm, which is often lauded by his contemporaries. Abraham Lincoln occasionally read Halleck's poetry aloud to friends in the White House.
American writer and critic Edgar Allan Poe reviewed Halleck's poetry collection Alnwick Castle. Regarding Halleck's poem "Fanny", he said, "to uncultivated ears... [it is] endurable, but to the practiced versifier it is little less than torture." In the September 1843 issue of Graham's Magazine, Poe wrote that the Halleck "has nearly abandoned the Muses, much to the regret of his friends and to the neglect of his reputation."
In 1870 a granite monument was erected to him in Guilford, Conn., the first monument ever erected in celebration of an American Poet.
In 1877 a statue was erected to him, the first statue to commemorate an American poet. It still stands on the Literary Walk on the Mall in New York City's Central Park.
In 2006 The Fitz-Greene Halleck Society was founded to raise awareness of this forgotten historical figure. The Society sees Halleck's value as a lesson of the fleeting nature of fame, but in no way seeks to mock the now almost completely forgotten poet.