That watch was the "most beautiful thing I'd ever seen," Stallone said in a video released by Sotheby's, and sparked a decades-long love of watch collecting.
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And now, the Hollywood star is auctioning 11 watches from his personal collection at a Sotheby's sale in New York on June 5. Among the items is the rare Patek Philippe Grandmaster Chime, which is expected to fetch as much as $5 million, as well as watches he wore in some of his films.
Only seven models of the Grandmaster Chime were ever made, given that it is the most complicated wristwatch ever manufactured by the famous luxury watchmakers.
As such, Sotheby's dubbed it the "holy grail" for watch collectors, appreciated for its extraordinarily intricate mechanisms that took 100,000 hours to develop, produce and assemble.
It features 20 complications - functions that go beyond telling the time - such as five chiming mechanisms and a date repeater which audibly indicate both the date and time.
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"This is not easy to come by," Stallone said. "I had to appeal to certain powers that be, write many letters to the board and eventually it was determined that I was going to be the owner of one of these magnificent pieces of art."
Other memorabilia comes with the watch too, including a presentation box engraved with Stallone's name and an iPad and Airpods each complete with a Patek Phillipe case.
Another Patek Philippe watch, this one from its Nautilus family, is expected to sell for up to $400,000. It features an olive-green dial, surrounded by 32 Wesselton baguette diamonds, in a stainless steel casing.
Several other notable watchmakers are represented in the auction too, including models that Stallone wore while on camera.
A Rolex watch released in 2016 to mark the 60th anniversary of a model that was the first to display both day and date separately could sell for $50,000.
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Meanwhile, a watch made by Audemars Piguet featuring a blue face inside a pink gold case is estimated to fetch up to $200,000.
Also included in the auction are several Panerai watches, a brand that Stallone has long championed and worn on camera in the 1996 movie "Daylight."
A model exclusively made for him, with an engraving commemorating that on the back, is among the watches featured in this auction and is expected to sell for up to $60,000.
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