Sylvester Stallone's Watches: 5 Most Awesome Timepieces in Sly's Collection

Sylvester Stallone is one of the most recognizable faces in Hollywood: an '80s legend whose name became synonymous with the action movie hero, he's had a recent resurgence at the box office thanks to movies that capitalized heavily on '80s nostalgia, like The Expendables. As of November 3, 2023, Stallone is the star of his own Netflix documentary, simply called Sly.

Unlike your typical action movie guy, there are countless layers to Sly, and that probably explains his career longevity in an industry that isn't exactly known for not being fickle. Hollywood is a cutthroat, dog-eat-dog industry where you're easily replaced if you step out of the spotlight for longer than a couple of years and where those who don't fit certain patterns stand no chance.

Throughout his decades-long career, Stallone was both these things, and this underdog theme is duly explored in Sly.

As it turns out, Stallone is also a very savvy businessman with a real estate portfolio that would make other celebrities feel poor by comparison, an accomplished artist, an auto enthusiast with an impressive collection, and, perhaps most surprising of all, a discerning watch collector – and occasional watch designer.

We'll focus on that last side of Stallone for now. So here are five of the most awesome timepieces that are – or were once – part of his enviable, multi-million collection.

Rolex Cosmograph Daytona "Big Red" Ref. 6263 – $100,000

Sylvester Stallone's collection is packed with Rolexes in different styles and from various eras of production. His most impressive Rolex, though, is a vintage piece that also happens to be one of the most coveted models from the entire lineup because it's one of the last manually-wound Rolexes: the Cosmograph Daytona "Big Red," which usually retails for around $100,000.

In production between 1971 and 1987, the 6263 was introduced at the same time as the 6265, from which it differed by the black Paul Newman dial. It's equipped with a 727 caliber and a 37mm stainless steel case with the black tachometer bezel with the big red "Daytona" inscription above the six-o'clock sub-dial.

This vintage Rolex Daytona, a classic gentleman racer's watch in every sense of the word, is a perfect fit for Sly's wrist that will almost always dwarf a less sturdy piece. The timepiece's character is also a perfect match for the guy who doesn't just play tough guys on the big screen but is one in real life as well.

Patek Philippe Nautilus 5711/1300A – $1 million-$1.4 million

The Patek Philippe 5711 is often called the "holy grail" of watches because it's very rare, very elegant, and... a Patek Philippe. Unlike modern timepieces that are covered in diamonds and gold, this watch is what you'd call a "simple" steel sportswatch, but this is a rare instance when "simple" also equals "super expensive."

Stallone's collection includes several Patek Phillipes because, as we've established already, the man has an eye for valuable collectibles. Patek Phillipe is a watchmaker that doesn't just deliver exquisite craftsmanship but also very few units per year compared to its industry peers. For example, whereas Rolex would churn out 1 million pieces per year for any given model, Patek Phillipe only makes a maximum of 60,000 units in the same timeframe, and that naturally drives prices up.

The 5711 Nautilus was introduced in 1976, and high pricing was part of the marketing strategy. Dubbed "one of the world's costliest watches made of steel," it's seen several iterations over the years – and Sly himself has several of them.

He has the 5711/1A with the blue dial and octagonal stainless steel bezel that retails for $170,000, but he also owns the diamond version, the 5711/1300A released in 2007, which features a dial in olive green and diamonds around the bezel and retails for $1.4 million.

Montegrappa Chaos Gold – $76,500

This is perhaps the most polarizing entry in this list, but that doesn't make it lack merit: the Montegrappa Chaos, described by the Italian press as "the worst thing to happen to Italy since Mussolini," is a limited-edition piece that was both inspired by and designed by Stallone. It all started with a pen he designed with Montegrappa to use on the set of the first Expendables movie.

Montegrappa designed the pen for Sly's Barney character but, sensing a market, ended up releasing it as a limited edition. This spilled into an extended collaboration that included other writing instruments and the Chaos Watch, offered in sterling silver, gold and enamel, and 18k gold, and a total of 399 pieces.

The Chaos Automatic Analogue Wristwatch stood out for the handmade case featuring skulls, lizards, and serpents, hiding the reliable automatic movement ETA 2824. At 54x43mm in diameter, the Chaos was anything but subtle: big and gaudy, it immediately caught the eye and kept it there with the intricate work of the interwoven serpent bodies and the oversize leather strap.

Taken out of context, the Chaos made no sense, and it was harshly criticized by those who did it. But if you think of it as a tie-in for The Expendables movie universe, it's actually a daring collectible – though probably the kind you'd rather keep at home, behind a glass case.

Panerai Luminor 5218-201/a – $214,200

This is the most obscure entry on the list and perhaps the most intriguing as well. Sylvester Stallone is actually credited with putting Panerai on the map, turning it from an obscure luxury watchmaker into a favorite with A-listers. Today's stars known for owning one such timepiece include Tom Cruise, Ben Affleck, Jason Statham, and Russell Crowe.

But before them, there was Sylvester Stallone. At the end of the 1950s, Panerai ended a long and successful partnership with Rolex, and business was declining as a result. When Sly chose to wear a Luminor 5218-201/a in the 1996 film Daylight, no one else in Hollywood was wearing one. Legend has it Stallone had bought the watch on a trip to Italy prior to the start of the production and loved it so much he wanted it to be a part of the Kit character in the film.

In 2020, that same Luminor piece sold for $214,200 at an auction, accompanied by a signed letter from Stallone and photographic evidence of the timepiece's star quality.

Richard Mille RM 25-01 – $1 million

Let's end this with a bang! Like with the other entries on this list, Sly owns several Richard Mille pieces. But this is the most outstanding of the lot, and not in the least because it was designed by and for Stallone himself. At the time it was introduced in 2019, Richard Mille said it was a piece that Rambo would wear.

And not only that, but it might save his life.

The RM 25-01 Tourbillon Adventure Watch was made in only 20 pieces, and one of them went immediately to Sly as a thank-you for being part of the creative process. Made with a titanium-carbon TPT case, the piece hides a tourbillon within the gears, a detachable compass, level, torque, chronograph, and power reserve indicator, and also features two interchangeable bezels, depending on whether you use it as a watch or compass.

As for its life-saving capabilities, these stem from a sealed compartment that holds five water-purifying capsules, allowing you to turn five liters of water drinkable in anything between 30 minutes and two hours. Not bad if you're ever in a Rambo-like scenario, right? As long as you have $1 million to spend on a watch, that is.