While modern-day watches are getting more accurate, slim and complicated than ever before, the most valuable and rare watches, much like automobiles, can only be found in the annals of history or, more accurately, at modern auction houses. From vintage Rolexes that once adorned the wrist of the biggest movie star in the world, to a super complicated pocket watch born of healthy competition between two tycoons – the tales told by these watches are as impressive as the innovations that powered them. 1. Rolex Paul Newman Daytona (Ref 6239) Seven years ago, the world of haute horology changed forever as a Rolex Daytona that once belonged to Hollywood star Paul Newman was auctioned for a record-breaking $17.8 million (Rs 151.5 crore). Why? Because not only was Newman the most bankable movie star of his generation, he was a bonafide semi-professional racer who never entered a race without his trusted Daytona Chronograph. Newman’s Daytona – a gift from his wife, actress Joanne Woodward – has long been considered the Holy Grail among watch collectors purely because of its ability to straddle multiple worlds : Hollywood, motorsport and horology. 2. Patek Philippe Henry Graves Supercomplication Not only is the Patek Philippe Henry Graves Supercomplication one of the rarest watches on the planet, it’s also the most valued and storied. Legend has it that the timepiece was created by Patek on special request by prominent 1930s New York banker Henry Graves Jr. Graves, who was in competition with fellow one percenter James Packard for whom Patek had made, in 1925 what was then the most complicated watch in the world, featuring 10 supercomplications. Not to be outdone, Graves immediately commissioned an even more complicated pocket watch – this one containing 24 complications. The watch boasts a double dial, a perpetual calendar, moon phase display, and a chronograph capable of timing two events at once. It also features Westminster chimes, indicators for sunrise and sunset times, and a celestial chart showing the night sky over New York’s Central Park—as viewed from Graves’ residence on Fifth Avenue. 3. Patek Phillippe Grand Master Chime Ref. 6300A - 010 Originally unveiled in 2014 to commemorate Patek’s 175th anniversary, the Grand Master Chime was, understandably enough, produced in very limited numbers. Only one made it to the corridors of history, the only version to feature a stainless steel case. The most complicated Patek Philippe wristwatch ever created, the Grand Master Chime features 20 complications displayed in two dials, an ebony black one and a salmon one for each side of the swiveling, reversible case with guilloché-patterned sides. 4. Vacheron Constantin Chronometre Royal Ref 4907 Launched in 1954, the Vacheron Constantin Chronometre Royal was produced in limited numbers, with the exact figure being unknown. Curiously enough, only one model ever made it to an auction house. That specific model, with its original silver dial remains free of any restorations, carrying the patina gathered over half a century and featuring faceted, applied white gold hour markers and raised enamel printing. The Chronometre Royal is famous not for its complications but for its era-defining precision and its well-preserved case. 5. Rolex Daytona Gold “Unicorn” Ref. 6265 Holding the distinction of being the second-most expensive Rolex ever sold publicly—surpassed only by Paul Newman’s legendary Daytona—is this one-of-a-kind white gold Cosmograph Daytona, famously dubbed the “Unicorn” for its unmatched rarity. Crafted around 1970, this extraordinary timepiece stands out not only for its rarity but also for its distinctive bark-finish bracelet, fashioned entirely from white gold. At the time, Rolex produced Daytonas exclusively in stainless steel and yellow gold, making the emergence of a white gold version a true revelation for collectors. Its scarcity and unusual finish instantly captured the attention of the vintage watch world. Housed within the 37mm Oyster case beats the manually wound Caliber 727, a 17-jewel movement renowned for its reliability and precision. 6. Breguet “Breguet et Fils,” Paris No. 2667 Precision 4 Abraham-Louis Breguet, the visionary behind the tourbillon and one of horology’s most revered figures, crafted this masterpiece with a yellow gold case engraved with a unique serial number. The engine-turned dial features a minute track and subdials bearing both Arabic and Roman numerals—one with yellow-gold hands, the other with blued steel—displaying local and mean time, along with a central sundial for seconds. Housed within the 63.7mm case is a groundbreaking dual-movement mechanism, each with its own barrel, pare-chute shock protection, and blued Breguet free-sprung balance springs—an extraordinary technical achievement for its era. 7. Rolex Zerographe Reference 4336 The first Rolex chronograph to feature an in-house movement, the Zerographe is one of the most coveted vintage Rolexes in the pantheon of rare 20th century watches. It was also the first Rolex watch ever to feature a rotating bezel. If those two factors weren’t enough to elevate the Zerographe to the stratosphere of haute horology, one must consider the fact that it was originally invented in 1937. It is estimated that only seven or twelve pieces were ever produced, howver only four examples are known to currently exist.