Sylvester Stallone, a recognizable figure in 1980s Hollywood, is a complex and often contradictory individual. His persona is a calm, likable presence that is genuine and true. He is also an artist, and his love of magnificent painting and sculpture lies at the heart of his highly personal work. He is not dishonest. Stallone is the only person responsible for his works. That strikes me as strong and powerful.

The legend is also known worldwide as a watch collector like his fellow celebrities Mark Wahlberg, Kevin Hart, John Mayer, etc. His collection varies from Rolex, Patek Philippe, Richard Mille to an independen brand Montegrappa.  

In his Instagram post in 2021, we can see that he wears a Rolex Oyster Perpetual 41mm 124300 in stainless steel with a green dial, that his huge wrist make it look smaller.

Introduced in 2020 the new Oyster Perpetual has been unveiled with a dynamic and vibrant new look, offering lacquer dials in five new colours: candy pink, turquoise blue, yellow, coral red and Rolex green. 

The basketball player LeBron James also owns two Oyster Perpetual - red and turquoise.

Retail price: $5,900.

Most watch collectors love the GMT-Master II Pepsi. So does the legend Sylvester Stallone. He owns the Pepsi on a jubilee bracelet. 

This model features a black dial and a two-color Cerachrom bezel insert in red and blue ceramic. Designed to show the time in two different time zones simultaneously during intercontinental flights, the GMT-Master II has come to be recognized for its robustness and versatile appearance.

The singer John Mayer also owns a Pepsi, but his model is the white gold Pepsi, instead of the steel. 

The legendary actor Sylvester Stallone seems to be a huge fan of Formula One. He was seen attending the Italian Grand Prix 2022 in September 2022. What interests the watch enthusiasts is the watch on his wrist: The stainless steel Rolex Daytona 6241 ‘Paul Newman’ black dial.

The Daytona 6241 is an extremely appealing variation of the model. It’s perfectly proportioned, and the combination of pump pushers and plexy bezel makes it a really wearable watch.

Stallone knows the best!

Now, the one you see in the picture is one of my favorite Rolex watches: It is the Rolex Day-Date 40 reference 228398TRU.

The timepiece is housed on an 18kt gold Rolex president bracelet and features a combination of red sapphire and an 18kt yellow gold diamond set bezel. The dial is diamond pave, and the hour markers are red rudy roman numerals. 

Powered by the Rolex 3255 caliber, the decked-out Day-Date features a 70-hour power reserve and has a water resistance of 100 meters or 330 feet

The market price on the grey market is close to $300,000.

Considering one of the most colourful, funnest, and playful modern watches, the Rolex Daytona Rainbow comes in three different models: rose gold (116595RBOW), yellow gold (116598RBOW), and white gold (116599RBOW). The yellow gold and white gold Daytonas were released in 2012 before the rose gold reference in 2018.

Retail price: $97,000.

Stallone owns several Patek Philippe Nautilus and one of them is the two-tone Patek Philippe Nautilus Chronograph 5980/1AR-001 in steel and rose gold, just like the piece owned by Robert Lewandowski. 

The 40.5mm watch features a blue sunburst dial, gold applied hour markers with luminescent coating, Sapphire crystal case back.

Moreover, the beauty is water-resistant up to 120 meters. The 28-520 C automatic chronograph caliber, with combined 60-minute and 12-hour counters, ensures precision. The energy source is a central rotor made of 21k gold.

Retail price: $73,850.

Market price: ~$110,000.

Just like the Croatian football player Luka Modric, Polish footballer Robert Lewandowski, actor Mark Wahlberg, etc., the legend also owns the white gold Patek Philippe Perpetual Calendar 5740.

Introduced as the first grand complication in the Nautilus collection, it features a blue sunburst dial with gold-applied hour markers and luminescent coating.  

Retail price: $126,850.

Market price: ~$250,000.

Another Nautilus he has is the one that also Prince Joaan of Qatar has. It is the 

Nautilus 5711/1300A made in stainless steel with a diamond-set bezel.

This model that was released in 2007 has the exact same identity of that of the old blue dial Nautilus, except this exact model comes in olive green dial and features also 32 baguette diamonds adorning the bezel.

Retail price: $ 94,620.

Market price: ~$1,400,000.

In the picture, we can see the iconic Richard Mille RM 032 Diver Flyback Chronograph on his wrist. 

Stallone wears this one in The Expendables 3. The rugged RM032 is the perfect companion for the equally rugged and gritty leader of The Expendables, Barney Ross, as he commands an elite group of mercenaries in a struggle against their former co-founder, arms dealer Conrad Stonebanks, now determined to eliminate the group.

In the case of the Richard Mille RM032, more is more, and the more rugged and complicated the watch, the more excitement it elicits. Combining a chronograph with an annual calendar function, rotatable bezel, and waterproof case, the RM032 flouts the traditional design and layout of the diver’s wristwatch. It has everything one might need to explore shipwrecks and coral reefs, and then some.

At 50mm diameter and 18mm in height, it has a commanding presence. 

I think the watch fits his larger than life personality well. 

Market price: ~$135,000.

His another Richard Mille is very iconic and also not in the signature shape. It is the RM 25-01 Manual Winding Tourbillon Chronograph Adventure.

Developed in collaboration with him, the RM 25-01 Adventure tourbillon chronograph attests a desire on the part of Richard Mille and the artist to conquer the most thoroughly hostile of natural environnements. Truly a horological UFO, this timepiece is, as Sylvester Stallone says, ‘Ready for action’.

The goal of the technical approach adopted by the RM 25-01 was to provide a tool that would allow these brave souls to get around safely, wherever they might be.

One of the interesting functions is the compass. It consists of a fixed bezel and a rotating bezel, both crafted in DLC-treated grade 5 titanium, with sapphire glass. It attaches to the case with a bayonet mount. Its cover is made of Carbon TPT®, and includes a mirror with an opening at 12 o’clock that permits greater precision when orientating with the compass needle.

The titanium bezel can be exchanged for a ‘daytime’ bezel should the owner so desire. This second bezel, in Carbon TPT® and grade 5 titanium, possesses marks for the four cardinal directions in addition to a 360° graduated disk and a 24-hour scale.

On the secondary market such as Chrono24, I saw that it sells for around $1 million. WOW!

And let's close this article with a watch that in my opinion is really cool! It is the  yellow gold Montegrappa Chaos, a 43mm watch made by Italian pen maker Montegrappa.

The entire case is covered in engravings. There is a prominent central skull over 12 o'clock, and the rest is covered with snakes and lizards.

The dial features thick sword-style hands and applied brushed Roman numeral hour markers.

Retail price: $76,500