Starting your career as a writing staff member at Saturday Night Live before leaving to write for The Simpsons is quite the way to enter the world of comedy. As a late-night talk-show host of almost 30 years, Mr Conan O’Brien specialises in relaxed interviews with everyone from Mr Robert Downey Jr to President Barack Obama, all while injecting quick-witted commentary. An essential role of the interviewer is recognising the right and wrong time to speak up. But O’Brien’s watch taste didn’t get that memo as he isn’t afraid to let his wrist game do plenty of the talking. Lately, the astute comedian wears some of the most striking and recognised watches from Panerai, Rolex and Omega, but as this archive image from the first year of Late Night With Conan O’Brien in 1993 shows, watches with sophistication and charm have long been a favourite of his.

In NBC’s hit US interpretation of The Office, Mr Steve Carrell as regional manager Michael Scott hangs a “certificate of authenticity” behind his desk, citing himself as “the proud owner of a Quality Seyko timepiece”. And in The Big Short, a filmmaking goof saw Carell as Mark Baum wear a Rolex Submariner 116610 from 2010, despite the film being set during the financial crisis of 2007 to 2008. Having undergone something of a personal style overhaul in 2017, it looks like his watch collection followed suit, graduating from Scott’s “Seyko” to the Rolex GMT Master II reference 116710BLNR. Known colloquially as the “Batman”, this modern classic can track multiple time zones at once while upholding the desirable Rolex sports watch DNA. It’s a class-leading example of a travel watch, one his “assistant to the regional manager” would undoubtedly approve of.

Mr Richard Pryor was a trailblazer in his field, considered by many as one of the founding fathers of observational comedy. Numerous comedians list his self-deprecating humour and gifted honest storytelling as being influential in honing their craft and voice, and it only takes a few minutes of watching his enthralling comedic delivery to see why. Over his 40-year career, his sharp dress sense and effortless style extended to his taste in watches. He often favoured the unassuming, elegant watches of the era, and from classic Cartier Tank-style pieces such as the one pictured to special pieces like the dual-time watch he was photographed wearing in 1968 for GQ, Pryor had an astute understanding of what watches made him tick.

It took New Yorker Mr Pete Davidson just one semester at college before deciding to drop out and pursue comedy full-time at the age of 20. Now, 10 years later, Davidson’s career as a comic, actor and writer has seen him host SNL, release three stand-up specials, and act in multiple major box-office pictures. His rapid rise to fame has also made him a key figure in pop culture, and looking at his watch collection, it’s clear Davidson is a big fan of one powerhouse of the watch world: Rolex. From a number of Datejust references – including the 41mm diamond-dial watch seen above (ref 126334) – uber-popular sports models such as the Submariner (ref 126610LN) and the perfect daily watch Day-Date 40 (ref 228238), Davidson is well equipped for every stage with his heavy-hitting coronet assemblage.

In the 1967 spy parody Casino Royale, Mr Peter Sellers wears a Rolex GMT Master reference 1675. In the true spirit of the film, Mr Ian Fleming’s original choice of Rolex for James Bond is believed to be the Submariner, making the somewhat symbolic interpretation fitting for the Bond spoof. Whether playing The Pink Panther’s Inspector Clouseau or Bluebottle in The Goon Show, Sellers was a born entertainer, with fellow comedians ranking him as the 14th most influential comedian of all time. As a success during the 1950s, 1960s and 1970s, Sellers had many truly great watches to choose from, and here, having an Italian lunch in 1965, his watch perfectly complements his effortlessly stylish demeanour. It’s sad to think that no matter how hard we try, we’ll never look this suave.

It’s easier to list the things Mr Donald Glover can’t do than the things he can, as the Californian-born star has music, acting, directing, producing, writing and comedy all mastered. Having won the Breakout Performer of the Year at the 2012 American Comedy Awards, a Golden Globe for his performance in the hit comedy-drama Atlanta, as well as five Grammys through his music career as Childish Gambino, this critically acclaimed performer finds even additional ways to make us envious with his impressive taste in watches. His collection very much mirrors his multi-faceted expertise, here spotted at the 75th Emmy Awards with an ever-timeless red Cartier Tank Must reference WGTA0190. Other favourites include a vintage Rolex GMT Master, a yellow-gold IWC Schaffhausen Portofino Chronograph, and a Cartier Santos De Cartier (WGSA0030).

From Not The Nine O’Clock News (1979) and Blackadder (1983) to Mr Bean (1990), Johnny English (2003) and Wonka (2023), Mr Rowan Atkinson is the definition of a multi-generational talent. As one of Britain’s best-loved actors, he remains a permanent fixture of the comedy landscape, with a decorated library of films and TV show hits. While many know him as a not-so-serious on-screen spy, away from his work, he’s been spotted almost always wearing a watch. Here dressed in white tie in 2011, Atkinson clearly shows his Ulysse Nardin Marine Chronometer – a brand he’s worn numerous times. Other favourites of the king of comedic timing include IWC Schaffhausen and Bell & Ross, indicating his taste in watches lies with quality tool watch manufacturers. Who can blame him?