To me, Sir Michael Caine has always personified charm and class, plus he tends to be the best dressed guy in the room. I’m not considered overly charming or classy, but I try to stand on the shoulders of Caine when getting dolled up for work. I often fail, but Michael Caine’s style is the goal for this reporter and, if I had a substantial amount of quid in my pocket, I would buy his first car, a 1968 Rolls-Royce Silver Shadow Two-Door Drophead coupe offered by H&H Classics at its Imperial War Museum auction on March 15. The U.K. auction estimates the Silver Shadow will fetch between £100,000 – 150,000. ($121,000 – $182,000)

“Depending upon which version you believe, the actor wandered into the renowned Jack Barclay showroom on Berkeley Square with a handwritten shopping list which read as follows: ‘milk, bread, newspaper, cigarettes, Rolls-Royce’,” the listing states. “Unkempt, unshaven and by his own admission possibly a little the worse for wear, he was given short shrift and ushered off the premises.

“Less than impressed, he journeyed onto Mayfair’s other Rolls-Royce dealership that of H.A. Fox on Dover Street. There he found a 1968 Rolls-Royce Silver Shadow Two-Door Drophead Coupe which had been taken into stock after the playwright and screenwriter Terence Rattigan cancelled his order for it (arguably best known for penning ‘The Yellow Rolls-Royce’, Rattigan already owned a 1966 Rolls-Royce Silver Cloud III Drophead Coupe). Having bought the car, Caine found it cheaper to employ a chauffeur than pay the premium his insurers quoted should he go down the ‘L-plate’ route. Apocryphally or not, the 35-year-old actor then took great pleasure in being driven past the offending Jack Barclay salesman and flicking him a V-sign!”

Caine owned the Silver Shadow for less than two-years and, in 1970, it was acquired by Jack Leach, owner of the Gasworks restaurant in Fulham that was frequented by A-listers like Richard Burton and his American bird. The Silver Shadow was re-registered as “ALO 182H” and was regularly driven by Leach until his passing in 2013. After Leach’s death it was put into storage and was subsequently sold to the current consignor, who commissioned an extensive restoration that the listing indicates “cost the best part of £100,000.”

Just 506 Silver Shadow Two-Door Drophead Coupes were handbuilt by Rolls-Royce’s in-house coachbuilder Mulliner Ward from 1967-1971, and this one was featured extensively in the 1969 documentary, “Candid Caine.” The sale includes V5C Registration Document, RREC copy chassis cards, restoration photos and numerous receipts.

“Personifying cool since the swinging sixties, Caine and the Silver Shadow remain instantly recognisable and widely admired,” says Damian Jones, Senior Motorcar Specialist of H&H Classics. “So, to combine both of these in one fantastic motor car is incredibly rare indeed and we expect significant interest from fans around the world.”

This article, written by David P. Castro, was originally published on ClassicCars.com, an editorial partner of Motor Authority.