The Pebble Beach Concours d’Elegance is the most prestigious car event in the world and each year, the best of the absolute best cars compete for Best of Show. The process begins with being accepted into the contest (a feat in and of itself) and then entered into an appropriate class, either by manufacturer (like Ferrari and Deusenberg) or by era and type (like postwar touring cars or British prewar cars). Those cars are judged and winners of those individual classes are chosen by class judges. Then, along with honors judges, the Best in Show is selected from the pool of category winners — this is why you might see a ’20s Bentley and a ’50s Ferrari up against one another for top honors.
Eventually, one car rises to the top and establishes itself as a truly special vehicle. Whether it’s a Ferrari custom built for a legendary Italian director or a concept car built for the 1933 World’s Fair, Pebble Beach’s 63 winners so far have had impressive histories and impeccable design. We’ve assembled some of the Concours’ most spectacular Best of Show recipients.
1950 Edwards R-26 Speed Sport Roadster

Usually, judges have a preference for prewar cars, but, with exceptional styling and elegance, the 1950 Edwards R-26 Speed Sport beat out the competition at the Concours’ inaugural year. San Francisco industrialist Sterling H. Edwards built the car with the help of race-car builder Norman Timbs, mostly to prove America could create a race car as successful as the Europeans. The R-26 was crafted from aluminum over a tube frame and powered by a Ford V8-60 engine.
1931 Pierce-Arrow 41 LeBaron Convertible Town Cabriolet

Back in the early to mid ’50s, when the Pebble Beach road race and Concours d’Elegance were operated in tandem, American racing legend Phil Hill had the honor of being the first and only individual to win both the race and the Best of Show in 1955. While he drove a 3.0-liter Ferrari to victory, it was the jaw-dropping looks of his Pierce-Arrow that stunned the judges. Coachbuilder LeBaron handled the car’s styling, and the car has been in the Hill family since brand new. It is now looked over by Phil Hill’s son Derek.