It’s hard to be as cool as Steve McQueen, but TAG Heuer’s Monaco watch comes pretty close. Sported by the screen legend in 1971’s auto racing film Le Mans, the piece was well ahead of its time. Featuring a string of firsts like an automatic chronograph and a water-resistant oversize square case—the Monaco, with its blue metallic dial and fire-engine-red hands, introduced a new wave in both technology and horological fashion. Another first? TAG Heuer, known for its precision in the auto-racing world, named Swiss driver (and McQueen pal) Jo Siffert its first official brand ambassador in 1969. And because Siffert was the inspiration for McQueen’s character in Le Mans, the star insisted on his very own Monaco for production. “The fact that he was very clearly wearing [the watch] in the film gave it a glamorous as well as rebellious image,” says Jack Heuer, honorary chairman of TAG Heuer. The timepiece—which TAG has reissued over the years in honor of, among other occasions, the King of Cool’s 75th birthday—has come to be known as the “McQueen Monaco.” McQueen’s real Monaco—the one seen in Le Mans—was auctioned at New York City’s Antiquorum in 2009. Sale price: $87,900.