The Canadian rock star and photographer was tasked with taking snaps of famous faces, also including Cher, Grimes, Jennifer Hudson, Iggy Pop, Normani, Saweetie and St. Vincent, for the iconic calendar's upcoming edition titled 'On The Road'.
And along with the unveiling of this year's Pirelli stars, a black and white shot of the 'Summer of '69' hitmaker taking the intimate photograph of the 30-year-old pop star in a hotel bathroom by Alessandro Scotti has been released.
Bryan, 61, can be seen standing on a toilet to get the money shot.
In a press release, the musician said: "On the road is where I have been for the last 45 years, because the life of a musician is made up of roads, travel, waiting in hotels, hours backstage."
Bryan spent just two days in Los Angeles shooting the pictures in June, and one day in Capri in July, where he took photos of rapper Saweetie, 28, at the Hotel La Scalinatella.
Music legend Cher, 75, was photographed backstage lit by the glow of dressing room mirror lights, experimental pop artist Grimes, 33, was captured in the process of creation, rocker Iggy, 74, can be seen painted in silver for an "after show celebration", while former Fifth Harmony star Normani, 25, was snapped leaning up against a tour bus.
Rapper Bohan Phoenix and R&B-pop star Kali Uchis also appear in the calendar.
The UK subsidiary of Italian tyre brand Pirelli started the calendar in 1964, with art director Derek Forsyth and British photographer Robert Freeman working on the first edition.
Over the years, the likes of Cindy Crawford, Miranda Kerr, Nicole Kidman, Hilary Swank and Uma Thurman have appeared in the calendar.
The presentation of 'On The Road' will take place in November, and will mark the return of the Pirelli Calendar after it was suspended last year due to the COVID-19 pandemic.