Jay-Z wore a platinum Rolex Day-Date on the cover of his 1996 album "In My Lifetime." That single image told the world exactly where he stood. And nearly 30 years later, celebrities with Rolex watches are still making the same statement — just with bigger collections, rarer references, and in some cases, over $4 million on one wrist.
In this guide, you will get the specific models. Not "a gold Rolex." The actual model name. The actual story. The actual reason it matters. From hip-hop artists to global athletes to Hollywood legends, we have covered all.
Hip-Hop Celebrities With Rolex Watches
No cultural world took Rolex further than hip-hop. Artists who came from nothing made Rolex the symbol of everything they built. These five names drove that story.
1. Jay-Z — Rolex Day-Date (Platinum) + Rolex Daytona (Sultan of Oman Commission)
Jay-Z's most documented Rolex is the platinum Day-Date, worn on the cover of "In My Lifetime" in 1996 and photographed repeatedly at press events, NBA Finals appearances, and interviews. The platinum Day-Date retails around $70,000. It features an ice-blue dial exclusive to platinum models, with a black Arabic numeral display he specifically chose over the diamond version.
But the most extraordinary Rolex in Jay-Z's collection is a Daytona commissioned exclusively by the Sultan of Oman. He wore it to a Hamptons party hosted by Michael Rubin. Of the eight examples ever made, produced from 1984 to 1986, a comparable example sold at Phillips auction in Geneva for $4 million. It is considered one of the rarest and most valuable vintage Rolex Daytona commissions ever produced.
Jay-Z also owns the first-generation ceramic-bezel Daytona — which he wears as his more casual piece.
Cultural significance: Jay-Z did not just wear a Rolex. He made the platinum Day-Date the defining symbol of hip-hop's relationship with generational wealth. Wearing it at 26 on an album cover was not about showing money. It was about writing a visual language that an entire culture would adopt.
2. Drake — Rolex Day-Date + Rolex Sky-Dweller (Diamond Meteorite)
Drake has stated publicly that he owns 143 Rolexes. His most frequently photographed model is the Day-Date in multiple configurations — yellow gold with diamond bezel on the GQ cover, white gold with diamond pave dial at a basketball game, pink dial white gold version at other appearances.
His most visually extraordinary piece is an off-catalogue white gold Sky-Dweller extremely rare factory diamond Sky-Dweller models produced in very limited quantities. The 42mm white gold case and bezel are factory-set with 74 baguette-cut diamonds. The dial is meteorite — a material formed from iron-nickel meteorites that shows a crystalline pattern called Widmanstatten that cannot be replicated. It sits on a black Oysterflex rubber strap with a diamond-set white gold clasp. Market value: approximately $700,000.
Cultural significance: Drake treats Rolex the way he treats music: constantly in rotation, never repeating the same thing twice. His 143-Rolex claim alone changed how people talk about watch collecting in hip-hop. He made accumulation part of the narrative.
3. Macklemore — Rolex Rainbow Daytona
Macklemore wears the Rolex Rainbow Daytona, which features a bezel set with multi-colored baguette-cut sapphires arranged in a gradient pattern and diamond hour markers on the dial. Retail pricing on a Rainbow Daytona runs from $200,000 to over $300,000 depending on configuration, and secondary market prices often climb higher.
Cultural significance: The Rainbow Daytona became the single most influential watch in hip-hop's recent history. Its arrival signaled a shift toward factory gem-set pieces over aftermarket custom work. Macklemore wearing it in music videos and live performances drove enormous secondary demand. It is the watch most credited with making rainbow gem-set pieces the new status standard.
4. Jay-Z (Honourable Mention Piece) — Rolex Daytona Steel (Ceramic Bezel)
Already counted above, but worth noting as a separate entry: Jay-Z wears the stainless steel Daytona with white ceramic bezel as what collectors call a "casual" piece. It retails around $16,000 and remains one of the hardest watches to buy at retail globally. On Jay-Z's wrist, paired with all-black fits, it functions as his understatement piece.
Athletes With Rolex Watches
Athletes choose Rolex for two reasons: performance credibility and visual authority. These six names cover both.
1. LeBron James — Rolex Day-Date 40 Everose + Rolex Daytona "Eye of the Tiger"
LeBron James was photographed wearing a Rolex Day-Date 40 in Everose gold at Lionel Messi's Inter Miami debut in July 2023. The Everose case features an olive-green sunray dial and President bracelet. Retail price: $41,500. The photo went viral because it showed LeBron snapping pictures of Messi while wearing a watch that costs more than most Americans earn in a year — and he called it his accessible piece.
His more extreme Rolex is the Daytona "Eye of the Tiger," a factory-set piece featuring a bezel with 38 baguette-cut diamonds and champagne sub-dials interwoven with brilliant-cut diamonds and black lacquer. Market value: approximately $300,000.
Cultural significance: LeBron is the most photographed athlete in the world. Every watch he wears enters public consciousness. The Everose Day-Date at the Messi game created a watch story that competed with the soccer story in terms of media coverage. That is the power of Rolex on the right wrist at the right moment.
2. David Beckham — Rolex Submariner
David Beckham is an official Rolex ambassador and has been photographed with the Submariner more than any other model. His black-dialed Submariner has appeared at Manchester United matches, fashion events, and years of public appearances. The black bezel, black dial steel Submariner retails around $10,000 and is considered by collectors to be the most versatile Rolex ever made.
Cultural significance: Beckham made the Submariner aspirational for men who exist between sport and fashion. He was the first major footballer to treat watch choice as a style statement rather than just an accessory. His black Submariner on a wrist full of tattoos became one of the most imitated watch looks in the world.
3. Tiger Woods — Rolex Deepsea
Tiger Woods served as an official Rolex ambassador for years and was regularly photographed wearing the Rolex Deepsea. The Deepsea is rated to 3,900 meters depth resistance and features a helium escape valve, RingLock system, and a 44mm case in steel. It retails around $13,750.
Woods wore the Deepsea during major tournament victories and post-game appearances, and the watch became visually associated with his comeback arc following multiple injuries.
Cultural significance: The Deepsea on an athlete says something specific: it is the most technically extreme Rolex ever made. Wearing it communicated that Woods chose the hardest option available. That alignment between athlete and object carried real symbolic weight during one of sports' most-followed comeback stories.
4. Alex Rodriguez — Platinum Rolex Day-Date 40 (Ice-Blue Dial)
Alex Rodriguez, former Yankees infielder and current CEO of ARODCorp, was photographed wearing a platinum Rolex Day-Date 40 with an ice-blue dial and darker blue hour markers. The ice-blue dial is exclusive to platinum models, appearing on no other metal variants in the entire Rolex catalog. This is a factory feature, not a customization.
Cultural significance: Rodriguez's watch choice reflects something specific about his post-baseball identity. The Day-Date 40 in platinum is the business world's Rolex. It sits on a platinum President bracelet and carries the visual language of corporate power. A-Rod picked it for an interview setting — not a game or a social event. That choice was deliberate.
5. Garbiñe Muguruza — Rolex Submariner "Cermit" (Green Ceramic Bezel)
Spanish tennis champion Garbiñe Muguruza is an official Rolex ambassador and was photographed wearing the 2020 Submariner nicknamed the "Cermit." The nickname combines "Kermit" (the prior green/black Submariner's nickname) with "ceramic" because the new model uses a black dial with green ceramic bezel. The case grew from 40mm to 41mm in this generation, and the bezel material changed from aluminum to Cerachrom ceramic.
Cultural significance: A professional female athlete wearing the Submariner rather than a Lady-Datejust or smaller model sent a clear message. Muguruza chose the sports watch made for serious physical use. That choice reinforced her on-court identity: all performance, no compromise on aesthetics either.
6. Cristiano Ronaldo — Rolex GMT-Master II "Ice" (Full Diamond)
Cristiano Ronaldo was spotted at the 14th Dubai International Sports Conference in 2019 wearing the Rolex GMT-Master II "Ice." Made from 18k white gold with nearly 30 carats of baguette-cut diamonds covering the case, dial, bezel, and bracelet, this is the most expensive watch Rolex has ever sold to the public. Original retail price: $485,350. Current secondary market value: approximately $796,000.
Ronaldo also wears the yellow gold Rolex Daytona Rainbow with a black mother-of-pearl dial and 36 baguette-cut rainbow sapphires on the bezel. His mother called it "a perfect combo" in an Instagram post.
Cultural significance: Ronaldo's watch choices match his philosophy: maximum output, maximum visibility, no apology. His GMT-Master II Ice is not a standard watch that was later customized — it is manufactured entirely in-house at Rolex with factory-set stones. That distinction matters to collectors. It is the hardest version of the most expensive Rolex ever made.
Hollywood Celebrities With Rolex Watches
Hollywood taught the world that a Rolex is as much a costume choice as a personal one. These six names show how the brand lives across different eras of the industry.
1. Paul Newman — Rolex Daytona ("The Paul Newman Daytona")
Paul Newman wore his Rolex Daytona for decades. The watch features what is now called the "Paul Newman dial" — an exotic dial with art-deco-style lettering, contrasting sub-register colors, and a distinctive crosshair pattern between the registers. Newman's wife, Joanne Woodward, had "Drive Carefully Me" engraved on the caseback.
When the watch was consigned to Phillips auction in October 2017, it sold for $17.8 million — setting the world record for the highest price paid for a wristwatch at auction. That record stood for years.
Rolex never officially named a dial variation after a celebrity before or since.
Cultural significance: The Paul Newman Daytona is the most important watch in the history of modern collecting. It changed how the entire industry values celebrity provenance. Before this sale, an actor wearing a watch was a style story. After this sale, it became a financial story. The watch market has never been the same.
2. Brad Pitt — Rolex Day-Date + Rolex Daytona + Rolex GMT-Master II
Brad Pitt owns all three of the most culturally significant Rolex models. His yellow gold Day-Date appears at formal events. His Daytona appears at casual settings. His GMT-Master II fills the middle ground. His collection is estimated at over $200,000 in total value, though he has never publicly detailed the specific references.
Cultural significance: Pitt uses Rolex the way serious collectors do: as a rotation. The right model for the right occasion. That approach — knowing when to wear a Presidential and when to reach for a Daytona — is what separates a real collector from someone wearing one watch forever.
3. Robert Downey Jr. — Rolex GMT-Master II
Robert Downey Jr. frequently posts Instagram photos wearing his GMT-Master II. The watch features dual time zones — marking both the current timezone and a second reference timezone via a 24-hour bezel ring. His model retails around $40,000. He also owns a vintage Submariner he wears for casual appearances.
Cultural significance: The GMT-Master II fits Downey's persona with unusual precision. It was designed for Pan Am pilots in the 1950s — people whose job required tracking two timezones simultaneously. An actor who travels constantly between film sets globally chose a watch literally designed for that life. That kind of alignment between person and object is what makes a celebrity watch choice interesting beyond the price.
4. Mark Wahlberg — Rolex Oyster Perpetual (Tiffany Blue)
Mark Wahlberg owns the Rolex Oyster Perpetual with the turquoise dial, often called "Tiffany Blue" by collectors. Rolex did not officially collaborate with Tiffany & Co. on this model. The nickname comes from the dial color resemblance. Due to extremely limited availability, secondary market prices increased significantly after release.
Cultural significance: Wahlberg paid a documented half-million dollars for a watch that originally sold at $6,150. That is not irrational. The Tiffany x Rolex collaboration is one of the most documented examples of scarcity creating explosive value in the watch market. For a man who came from Dorchester, Boston, spending $500,000 on a watch because it is the right watch is its own kind of statement.
5. Jennifer Garner — Rose Gold Lady-Datejust
Jennifer Garner wears the Lady-Datejust in rose gold with a champagne dial and diamond hour markers. The 28mm case fits a smaller wrist while maintaining all the precision and prestige of the full Datejust. She has worn it at film premieres, while dropping kids at school, and at press events — which is exactly the functional range the Lady-Datejust was designed for.
Cultural significance: Garner's choice illustrates something most Rolex coverage ignores: the Lady-Datejust is not a smaller version of a man's watch. It is a full watch in its own right. The rose gold model with diamond markers communicates that Garner does not adjust her jewelry choices based on whether she is on a red carpet or a school run. That consistency is its own kind of style authority.
6. Christopher Plummer — Vintage Rolex Daytona (Manual-Wind, Black Dial)
Christopher Plummer was photographed wearing a vintage stainless steel Rolex Daytona with a black dial and white registers at a press conference for "All the Money in the World" in December 2017. He passed away in February 2021 at age 91.
This is a manually-wound Daytona from the late 1970s with a black tachymeter bezel — one of the final manually-wound generations before Rolex introduced automatic movements. Collectors prize these late manual-wind examples for their clean, understated dial design.
Cultural significance: An actor who played one of film's most memorable villains (in "Knives Out") and most celebrated patriots (in "The Sound of Music") wore a quietly significant vintage Rolex at a professional event. That watch does not announce itself. It rewards the people who know what they are looking at. That is the correct watch for a man of Plummer's stature.
Music Icons and Global Figures With Rolex Watches
These two musicians and one world leader each with a different relationship to Rolex and what it represents.
1. Lenny Kravitz — Vintage Rolex Daytona (Black Tachymeter Bezel)
Lenny Kravitz — musician, producer, photographer, and designer — wears a vintage Rolex Daytona with a black tachymeter bezel and matching black dial. He wore it on a leather bund strap rather than the standard Oyster bracelet, a modification that puts the watch closer to the skin and gives it a completely different visual character.
In 2016, Kravitz collaborated with Les Artisans de Genève to create a limited edition of 55 pieces based on a two-tone Daytona.
Cultural significance: Kravitz has always preferred vintage to new, original to derivative. That vintage Daytona on a bund strap is not a compromise — it is a deliberate statement about how to wear a classic object in a way that is fully personal. No one in music handles a Rolex with more individual conviction.
2. Lisa (Blackpink) — Two-Tone Rolex Datejust
Lisa, member of Blackpink and now a solo artist, wears a two-tone Rolex Datejust with a blue dial and diamond hour markers valued around $15,000. She frequently showcases it on social media to an audience of over 100 million followers across platforms.
Cultural significance: Lisa is arguably the most influential watch-wearer among Gen Z globally. Her Datejust has introduced Rolex to an audience that did not grow up in the hip-hop or sports world. Her wearing it with the same ease as a rapper or a retired president is a signal that the brand's cultural reach in 2024 is fully borderless.
3. Barack Obama — Rolex Oyster Perpetual (Steel, White Dial)
Barack Obama has been photographed wearing a Rolex Oyster Perpetual in stainless steel with a clean white dial on multiple occasions since leaving the presidency in 2017. The Oyster Perpetual is Rolex's most stripped-back model: no date, no bezel complications, no precious metal. Just the core movement in a clean case.
Cultural significance: A former president of the United States, who could wear anything on his wrist, chose the simplest Rolex made. That choice communicates authority without needing to prove it. In collecting culture, this is called "understated confidence." Obama's Oyster Perpetual says: I know exactly how little I need to say.
The 4 Rolex Models Celebrities Rolex Watches Choose Most
Looking at these names, four models appear again and again.
The Day-Date (Presidential): Jay-Z, Drake, LeBron James, Brad Pitt, Alex Rodriguez, Barack Obama's group. Exclusively available in 18k gold or platinum. Never made in stainless steel. Entry retail: approximately $35,000. The most documented luxury watch in hip-hop history.
The Daytona: Jay-Z, Macklemore, Brad Pitt, Paul Newman, Christopher Plummer, Lenny Kravitz, Cristiano Ronaldo. Originally built for racing drivers. The Paul Newman sale changed how the world values Rolex permanently.
The Submariner: David Beckham, Garbiñe Muguruza, Brad Pitt. The world's most recognizable sports watch. 300-meter water resistance. Produced since 1953. Steel entry price around $10,000 to $14,000.
The GMT-Master II: Robert Downey Jr., Cristiano Ronaldo, Drake. Originally designed for Pan Am pilots in the 1950s. Tracks two time zones simultaneously. The "Pepsi" and "Batman" bezel variants are the most sought-after secondary market pieces.
Why Celebrities Choose Iced-Out Rolex Over Stock Pieces
The watches above represent one end of the Rolex celebrity spectrum. The other end is the iced-out custom Rolex.
Here is how it works: a stock Rolex is sent to a certified jeweler. The factory metal is replaced with diamonds — VS clarity or better — across the case, bracelet, bezel, crown, and in some cases the dial itself. The result is a watch that shares a case with a Rolex but looks nothing like one at first glance.
Drake's diamond Sky-Dweller. Lil Wayne's fully paved Daytonas. Ronaldo's GMT-Master II Ice (factory diamond-set, not aftermarket — a critical distinction Rolex makes internally at Rolex's own gem-setting studio in Geneva).
The fully iced look runs from $50,000 on a modest stock Submariner to over $500,000 on a Day-Date with VS diamond coverage on every surface.
If the celebrity watch aesthetic speaks to you but the Rolex price does not, that gap is exactly where Glazed Diamonds builds. Our hip-hop jewelry collection and diamond watch collection are built around the same visual language, with the same standards of stone coverage and craftsmanship, at a price point that reflects your intelligence as a buyer.
Explore our luxury moissanite watches for men collection that carry the full wrist presence of a diamond-set Rolex without the six-figure price tag.
Please review our returns policy before purchase.
Conclusion
These celebrities with Rolex watches are not telling the same story. Jay-Z used a platinum Presidential to write a new chapter of hip-hop culture in 1996. Paul Newman wore a manual-wind Daytona for decades until it became the most valuable wristwatch ever auctioned. Drake built a collection of 143 because the accumulation itself is the statement. Obama chose the simplest Rolex made because he needed to say nothing more.
The watches are different. The message is consistent: they know exactly what they are wearing and why.
At Glazed Diamonds, we build for people who understand that language. Whether you are drawn to the Presidential power of the Day-Date, the iced-out world of the custom Daytona, or the clean authority of the Submariner, we have pieces built around the same visual thinking.
Frequently Asked Questions
Which celebrity has the most Rolex watches?
Drake is widely known as the biggest Rolex collector among celebrities. He has said he owns over 140 Rolex watches, including rare Day-Date and diamond Sky-Dweller models.
What is the most expensive Rolex ever worn by a celebrity?
Paul Newman’s Rolex Daytona became the most expensive ever, selling for $17.8 million at auction. Cristiano Ronaldo’s diamond GMT-Master II Ice is also one of the most expensive modern Rolex watches.
Why do so many hip-hop artists wear the Rolex Day-Date?
The Day-Date is made only in gold or platinum, which makes it a strong symbol of wealth and success. Many rappers wear it to represent achievement and status.
What is a Paul Newman Daytona?
It is a rare vintage Rolex Daytona with a special dial style worn by actor Paul Newman. His personal watch became the most valuable Rolex ever sold.
What is the difference between an iced-out Rolex and a factory diamond Rolex?
An iced-out Rolex has diamonds added by a jeweler after purchase. A factory diamond Rolex has diamonds set by Rolex itself, which makes it more valuable and collectible.
Are there Rolex alternatives for people who want the celebrity watch aesthetic?
Yes. Moissanite and lab-grown diamond watches offer the same luxury look and shine at a much lower price than a real Rolex.
What Rolex model is best for a first-time luxury watch buyer?
The Submariner is the best starting Rolex. It is durable, easy to wear daily, and one of the most recognized luxury watches in the world.
