Legendary founder and editor-in-chief of Playboy magazine, Hugh Hefner, died yesterday at the age of 91. While Hef may not have been known as an avid automotive enthusiast, much of his life was surrounded and accented by over-the-top rides. Most people don't know that the name of his now famous empire was inspired by a defunct automaker with the same name, as the story goes.

The Playboy Automobile Company was founded in 1947 in Buffalo, New York. Though it wasn’t anywhere near as successful as other American automakers that came before or after, the respectable, small manufacturer built a handful of cars before it went out of business in 1951.

A total of 97 cars were produced between 1947 and 1951, the first and most notable being the Continental. Under the hood was a 40-horsepower (29-kilowatt) four-cylinder engine, and its advertised top speed was just 75 miles per hour (121 kilometers per hour). With a wheelbase of just 90 inches, and a total length of just 156 inches, it was a tiny car. The magazine that soon followed, though, was anything but.

Gallery: Playboy Automobile Company

Playboy Magazine was founded in 1953. The name reportedly came from an employee of Playboy Automobile Company who suggested to her son's friend that he call his new magazine 'Playboy.' That friend was Hugh Hefner.

Like the auto manufacturer after which it's named, the magazine had its sights set on a male-dominated audience. The men’s lifestyle brand was one of the first of its kind – but it wasn’t all just about beautiful women. Cars were an integral part of the Playboy personality, specifically in the magazine’s Playmate of the Year award, which was given out annually beginning in the mid-60s.

The first Playmate of the Year was Lisa Winters in 1953. But it wasn’t until 1964 that the company began including a vehicle prize along with the honor. Donna Michelle was the first to be awarded a car as Playmate of the Year in 1964 – a tacky bright pink 1964.5 Ford Mustang complete with a 289 V8 (pictured below).

1964 Playmate Car Of The Year

The award continued on annually from then, and varied in uniqueness from an odd Lamborghini Countach Roadster kit car, awarded to India Allen in 1988, to the Eagle Talon (below, upper left), given to Julie Lynn Cialini in 1995. The most recent winner of Playmate of the Year, Eugena Washington in 2016, took home a brand new Fiat 124 Spider. Other unique offerings included a Mazda 6 in 2009, a Shelby Series 1 in 1998 (below, bottom right), a pink Volvo P1800 in 1973 (below, upper right), and a Plymouth Barracuda in 1967 (below, bottom left).

Playmate Of The Year Cars
Playmate Of The Year Cars
Playmate Of The Year Cars
Playmate Of The Year Cars

Alongside Playmate of the Year, Hef himself was known for his impressive selection of vehicles. The Playboy Mansion was often pictured with a 1969 Mercedes-Benz 600 Pullman limousine in the driveway, typically alongside a first-generation Maserati Ghibli, a Mercedes-Benz 300 SL convertible, or both.

Playmate of the Year, the magazine’s annual Car of the Year award – which saw winners like the Porsche 911 Carrera GTS in 2015, and the Jaguar F-Type in 2014 – and its heavy involvement in motorsport cemented the magazine, and Hefner, in history as an automotive influence to be sure.

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