Drake Flexes ‘Rare As Rocking Horse S***’ Rolex At Kentucky Derby

Rapper rocks rare Rollie at the races.

Drake Flexes ‘Rare As Rocking Horse S***’ Rolex At Kentucky Derby

The hip-hop superstar is well-known for his love of the finer things… So it’s perhaps not a surprise he was spotted at one of the world’s most famous horse races wearing an exceedingly rare new Rolex.


Drake is living his best life in 2022, with the 35-year-old Canadian making more money and selling more records than ever.

Indeed, Billboard has just come out and shared data that shows Drake generated more music streams in 2021 than every song released prior to 1980 combined. Even with the pittance streaming services pay, that’s a lot of moolah.

Perhaps that’s why he’s splurged on yet another ridiculously expensive watch. Chilling at the Kentucky Derby last week with fellow rapper Jack Harlow, Drizzy was spotted rocking a rare Rolex Sky-Dweller ‘2021 Secret Release’ (ref. 326259TBR) worth well over AU$1 million.

Images: @champagnepapi / Chrono24

As the name suggests, this Rolex isn’t available to regular punters. It’s an off-the-catalogue special that’s only offered to Rolex’s biggest-spending customers. The watch is so rare, few pictures of it exist online – so Drake’s really blessed us by offering us a glimpse.

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Featuring an 18ct white gold case, meteorite dial and almost completely paved with diamonds, this hefty Sky-Dweller is a real rapper’s watch. Normally mounted on a similarly paved white gold bracelet, Drake has instead opted for the Oysterflex version of this piece, which is slightly more sporty and much more comfortable.

Drake wasn’t just at the Kentucky Derby to take in the atmosphere (although he certainly did plenty of that – as BlogTO reports, Drake got hilariously drunk at the race). He was actually there to film a music video for Jack Harlow’s track Churchill Downs, on which he appears as a featured artist.

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