The star of the show was a bottle of LeNell’s Red Hook Rye 23 Year Old Barrel #1, which sold for $56,250 (£44,814).
That smashed the estimate of $20,000 to $30,000 at Sotheby’s ‘Festive Spirits and American Classics’ auction in the Big Apple.
LeNell Camacho Santa Ana owned a specialist spirits store in the Red Hook area of Brooklyn back in the 2000s.
She regularly embarked upon buying trips to Kentucky, and one of her excursions saw her land four barrels of rye that had been distilled at Bernheim Distillery in Louisville in the early 1980s.
It was used to create LeNell’s Red Hook Rye, which has emerged as one of the most distinctive and sought-after rye bottlings of all time. The 23 Year Old Barrel #1 was signed by Camacho Santa Ana.
Zev Glesta, spirits specialist at Sotheby’s, said it had secured some of the ‘rarest whiskeys that only surface once in a blue moon’ for the auction.
A bottle of Rathskeller Rye 136 Proof 1983 shattered its target of $18,000 to $24,000 by fetching $37,500 (£29,876).
The 24-year-old rye was commissioned by the Seelbach, Louisville’s grandest hotel, in 2007 to commemorate the building’s rich history.
Another highlight was a bottle of D.H. Cromwell 15 Year Old, which sold for $30,000 (£23,900) – $10,000 higher than the upper estimate.
It is one of just 72 bottles of this whiskey, which was produced by Julian ‘Pappy’ Van Winkle III at his Old Commonwealth Distillery.
The whiskey pays tribute to a Milwaukee bar owner called Helen Cromell, who often added a ‘w’ to her name to make it easier to remember.
She became a close friend of Pappy Van Winkle, so this bottling was created in 2000 to honour her memory.
Cromell was nicknamed Dirty Helen for her ‘spicy vocabulary’, and the label bears the letters VGS, short for ‘very good s***’.
Meanwhile, a bottle of Old Rip Van Winkle 25 Year Old 1989 sold for $37,500 (£29,876), which was $7,500 above the upper estimate.
It is the oldest Van Winkle whiskey ever released, nicknamed the ‘Pappy of Pappys’. It is known as the best, rarest and most coveted bottle the Julian Van Winkle III ever produced.
It was released in a run of just 710 bottles back in 2014, and it features some of the last Stitzel-Weller bourbon made at that distillery before it shut down.
A bottle of Van Winkle Special Reserve 19 Year Old Corti Brothers sold for $22,500 (£17,925), while another sold for $20,000 (£15,934).
The Corti brothers ran a gourmet grocery store in Sacramento in the 1980s, which became one of the earliest buyers of Pappy Van Winkle whiskeys.
Owner Darrell Corti is credited with convincing Van Winkle to use a cognac-style bottle, which is now one of the distillery’s hallmarks.
Twelve bottles of A.H. Hirsch sold for a total of $88,750 (£70,725). The highlight was an A.H. Hirsch 19 Year Old bottle from 1974, which fetched $11,875 (£9,462).
A bottle of Michter’s Single Barrel Rye 25 Year Old also beat its upper estimate by selling for $23,750 (£18,923).
