When Stephen Colbert landed The Late Show in 2015, he received two notable calls. One from David Letterman, whom he’d be replacing; the other from Letterman’s rival, former Tonight Show host Jay Leno.

“Jay called me right away, and he was lovely,” says Colbert, as he slips into a Leno impression: “He goes, ‘Yeah, you got the pope job. You got the job ’til you’re dead.’ Well, you were wrong on that one, Jay.”

Paul Smith suit, shirt, tie;

Omega watch; Oliver Peoples reading glasses; stylist’s own pocket square.

Photographed by Guy Aroch