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The Most Iconic Rolex Watches and the Legends Behind Them

by jingji41

Few brands command the universal recognition and prestige of Rolex. Founded in 1905 by Hans Wilsdorf, the Swiss watchmaker has spent nearly 120 years cementing its reputation as the pinnacle of luxury timekeeping. Synonymous with precision, durability, and status, Rolex has crafted watches worn by explorers, presidents, and cultural icons. Below, we explore the most legendary models and the figures who helped elevate them to horological royalty.

Rolex Land-Dweller: A Modern Classic

Debuting in 2025 at Watches and Wonders, the Land-Dweller is Rolex’s latest innovation. Tennis legend Roger Federer unofficially unveiled it with a wrist shot, sparking immediate buzz. The design pays homage to the 1970s Oysterquartz with an integrated bracelet, while the Calibre 7135 movement introduces the groundbreaking Dynapulse escapement for unparalleled accuracy. Early adopters like Leonardo DiCaprio have already secured theirs, ensuring its place in the spotlight.

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Rolex King Midas: The Golden Exception

Designed by legendary watchmaker Gérald Genta, the King Midas defies Rolex’s typical sporty aesthetic with its bold rectangular case. Crafted entirely from 18-karat gold, it earned its name from the Greek myth of King Midas. Elvis Presley and John Wayne were among its earliest admirers, while modern collectors like Travis Scott keep its legacy alive. Discontinued in 1972, the King Midas remains a rare and revered piece.

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Rolex DeepSea: Built for the Abyss

Rolex’s commitment to pushing boundaries is epitomized by the DeepSea. Originally developed for professional divers needing a watch capable of surviving 1,000-meter depths, it evolved with innovations like the helium escape valve. The James Cameron Sea-Dweller, tested at 10,908 meters in the Mariana Trench, stands as a testament to Rolex’s engineering prowess. Though its 44mm case is imposing, its reliability is unmatched.

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Rolex Oyster Perpetual: Timeless Simplicity

The Oyster Perpetual, introduced in 1926, was the world’s first waterproof wristwatch. Its self-winding movement set a new standard. Today, the brightly colored lacquer-dial versions, like the coveted Tiffany Blue, command double their retail value. Kendrick Lamar’s Grammy appearance with one solidified its cultural cachet, while the recent “Bubble Dial” edition offers a playful twist for collectors.

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Rolex Explorer: The Mountaineer’s Choice

Born from Rolex’s 1953 Everest expedition, the Explorer is the epitome of understated elegance. Its clean black dial with luminescent 3-6-9 numerals has adorned the wrists of Ian Fleming and Tom Hardy. The 36mm version, favored for its classic proportions, remains a purist’s dream.

Rolex GMT-Master II: The Jet-Setter’s Companion

Created for Pan-Am pilots in 1955, the GMT-Master II revolutionized travel with its dual-time-zone display. Nicknamed after its bezel colors—like the “Pepsi” and “Batman”—it’s a favorite among globetrotters. The 2023 left-handed “Destro” edition, worn by Russell Westbrook, added a fresh twist to this iconic line.

Rolex Datejust: The Everyday Icon

Launched in 1945, the Datejust was the first watch with an automatic date window. Its versatility has made it Rolex’s best-selling model, worn by figures from Martin Luther King Jr. to Rihanna. Despite its ubiquity, its timeless design ensures enduring appeal.

Rolex Day-Date: The Presidential Statement

Exclusive to precious metals, the Day-Date debuted in 1957 with its signature “President” bracelet. Lyndon B. Johnson popularized its nickname, while modern admirers include Drake and the Dalai Lama. The 2024 “Emoji” edition, replacing dates with affirmations, showcases Rolex’s playful side.

Rolex Milgauss: The Scientist’s Watch

Designed for CERN researchers in 1956, the Milgauss withstands 1,000 gauss of magnetic interference. Its lightning-bolt seconds hand and Z-Blue crystal make it a standout. Tom Hanks, an early adopter, remains one of its most notable fans.

Rolex Submariner: The Dive Watch Benchmark

The Submariner set the standard with 100-meter water resistance in 1953. Though criticized by some as “basic,” its legacy is unshakable—worn by Jacques Cousteau and Al Pacino alike.

Rolex Daytona: From Underdog to Legend

Initially overlooked, the Daytona rose to fame through motorsports and Paul Newman’s endorsement. His personal model fetched $17.8 million at auction, cementing its status. Today, it’s a favorite of Jay-Z and John Mayer.

Rolex Yacht-Master: Luxury on the High Seas

Introduced in 1992, the Yacht-Master offers a refined alternative to the Submariner. Brad Pitt and Nick Jonas have sported its white-gold and custom editions, embodying its upscale allure.

Rolex Sky-Dweller: The Modern Traveler’s Watch

Released in 2012, the Sky-Dweller caters to global nomads with its dual-time-zone complexity. Tom Cruise and LeBron James favor its bold 42mm design.

Rolex Air-King: A Nod to Aviation History

Born in the 1930s, the Air-King gained cult status through Domino’s Pizza’s employee rewards. Vintage models now fetch up to $19,000.

Rolex 1908: A Return to Elegance

The 2023 Perpetual 1908 revives Rolex’s dress-watch heritage. Roger Federer’s early adoption highlights its appeal for collectors seeking timeless sophistication.

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