Comedian Dave Chapelle spotted wearing a Apple

Spotted during his guest appearance on Season 10, Episode 2 of Jerry Seinfeld's web series 'Comedians in Cars Getting Coffee,' Dave Chappelle keeps things characteristically low-key on the wrist. The setting — a car interior, relaxed conversation — is exactly the kind of context where a person's everyday watch choice reveals more than any red carpet outing. Chappelle opts for an Apple Watch in Space Black stainless steel with a matching Space Black Milanese Loop band, a combination that projects quiet confidence without performative flex.

The Space Black stainless steel Apple Watch with Milanese Loop was introduced with the first-generation Apple Watch in 2015 and quickly became one of the most sought-after configurations in the lineup. The PVD-coated stainless steel case offered a darker, more formal aesthetic compared to the standard silver finish, while the Milanese Loop — a continuous fine-mesh stainless steel bracelet with magnetic closure — referenced the centuries-old Italian weaving technique that Swiss and Italian watchmakers had long employed on dress watches. It was Apple signaling, loudly but elegantly, that it understood watchmaking heritage.

From a collector and enthusiast standpoint, the Space Black Milanese Loop combination occupies an interesting position. It was discontinued after the Series 3 era, making earlier examples mildly desirable for those who preferred the darker PVD treatment that Apple later moved away from. The Milanese Loop itself has remained in the Apple Watch ecosystem but without the Space Black PVD treatment in later years, adding a quiet rarity to the original configuration.

Dave Chappelle's watch choices have never been the story — and that is precisely the point. The comedian, who famously walked away from a $50 million Comedy Central deal in 2005, has long operated outside the conventional celebrity playbook. Wearing a functional, design-forward smartwatch rather than a six-figure mechanical piece aligns with his broader persona: sharp, deliberate, unbothered by expectations.

On the secondary market, early Space Black Apple Watch stainless steel models with Milanese Loop command modest premiums among collectors of Apple memorabilia and early wearable tech, though values remain well below traditional luxury timepieces. Retail at launch ran approximately $1,099 for the stainless steel Milanese configuration — a price point that positioned it firmly against entry-level Swiss competition.