Sylvester Stallone says a Monet he bought for about $110,000 was later offered back to him for roughly $130 million. His art collection delivered what he describes as his biggest paydays, but selling paintings before their prices climbed further left him with regrets.

Speaking on The Overlap podcast, the Rocky star recalled putting his movie earnings into art in the mid-1980s. He described buying paintings, selling them for $3 million and then being approached 10 to 12 years later with offers to buy them back for $75 million.

“I had a collection that you can’t replace because of the shift in finances,” Stallone said.
He still owns work by Pablo Picasso and Andy Warhol. Asked about the value of those pieces, he answered: “About $40 million … for just one.” His collection also includes contemporary artists George Condo and Rashid Johnson, whom he called “this generation’s Picassos.”
His advice to collectors: “Don’t sell it unless you’ve got to pay the mortgage because it’s appreciating.”
Stallone says he’s turning his attention to vintage watches next, claiming some can rise to 10 times their purchase price. He’s particularly interested in hand-painted Rolex Stella watches and says he’s already acquired almost the whole collection.
