The Hugh Hefner story is an intriguing one. In his younger years, before he became a famous figure of the adult entertainment industry, Hefner wrote and illustrated comic books. No one probably expected him to go on to become a successful entrepreneur, let alone live out a rags-to-riches tale. Although Hefner passed away a few years ago, he left behind an indelible legacy, leaving proof the American Dream exists and is attainable. Even though he didn't come from a rich background, Hefner was able to start a business that allowed him to live comfortably for the rest of his life. His lavish and decadent lifestyle was widely known and coveted.
Updated April 2022: Hugh Hefner may not be the best rolemodel, but there's no denying that he had a great taste in cars, so for that reason, we updated this article with more facts about some of the coolest models he owned as well as gave away to his models.
Known for hosting extravagant parties where celebrities and major personalities were all in attendance, the Playboy Mansion symbolized the pinnacle of Hefner's fortune. There's an amazing fact behind Hefner starting Playboy and launching his entire business. According to CNBC, Hefner used just $600 to kick off the publication, which resulted in an enterprise worth hundred's of millions of dollars. Along the way, Hefner acquired a few cars as a way of adding to his status as a sophisticated entrepreneur. As someone who recognizes cars and what they represent, Hefner and his business went out of the way to award its female models with automobiles. If they became models of the year, they often got their own car. Here's a look at some of Hugh Hefner's cars in his collection along with some of the best cars Playboy awarded to its standout models year after year.
18 Lamborghini Countach
Lamborghinis are highly regarded among many as the pinnacle of performance and status. That makes it the perfect kind of car to gift to a Playboy model. The Drive reports that India Allen received this Lamborghini Countach thirty years ago back in 1988.
While the source goes on to report that she’d go on to play a part years later in the infamous O.J. Simpson trial, it’s her Lamborghini we remember most. These cars can reach a decent 186 mph top speed, according to AutoZine, which may have been the same speed it went at while driving off the Playboy Mansion lot.
17 Cadillac Series 62
Hugh Hefner was born in the 1920s. As a result, he got to see a majority of the 20th century, including all of its classic cars over the years. Having witnessed so many memorable cars, it’s no wonder Hefner got hooked on them. According to The Drive, this 1955 Cadillac is what started his love for automobiles.
While the car may sound outdated by today’s standards, it was rather advanced for its day. The same source notes that features like the automatic windshield wipers were newer features in its day. It fits Hefner to have a luxury car like this, considering his lavish lifestyle.
16 De Tomaso Pantera
There are plenty of cars that have gone through Hefner’s garage into the hands of awarded Playboy models. While many are unimpressive, this De Tomaso Pantera is an exception. According to AutoGuide, the model Liv Lindeland got this high-performing car that can deliver an impressive 330 hp.
With performance like this, it’s easy to forgive the car's hot-pink paint coating. The same source reports that this car would’ve set buyers back a little more than $10K when it came out in the early ‘70s. Playboy didn’t go the frugal route when they awarded this car in 1972.
15 Mercedes-Benz 300 SL
Hugh Hefner didn’t practice modesty when it came to cars; his Mercedes-Benz 300SL is proof of that. According to The Drive, these can cost up to $1 million, which leaves these for top 1 percenters. Sometimes, it’s less about the car's features or performance and more about how much it's worth.
Even if it only served as another one of his trinkets, it's not a bad one to have. From the car’s aesthetic alone, one can easily tell these are reserved for exceptional entrepreneurs of the world. It’s easy to see why Hefner kept one of these in the Playboy Mansion garage.
14 Plymouth Barracuda
Hefner may have had trouble parting with this Plymouth Barracuda. To let someone take this off his hands and the Playboy Mansion grounds must've stung at first. The good news is—according to AutoGuide—that Plymouth made several more like it following the donation to Lisa Baker.
The same source goes on to speculate about the engine displacement. These model cars came with two engine versions, either a 225 or a 383 cu in. While it’s not exactly clear which engine displacement Baker got for her Plymouth Barracuda from Playboy, it’s a beautiful and stylish car nonetheless—even if it's painted pink.
13 Mini Roadster
The cars Playboy gives out to its best models are the cherry on top. According to Auto Evolution, Hefner himself chooses what models get the car each year. In 2014, Kennedy Summers got a Mini Roadster straight from the Mansion. It may not be the best car on the list, but it’s a free car nonetheless.
What’s ironic is the fact that of all the cars on this list, the Mini Roadster should’ve had a pink paint job. Playboy appeared to have stopped that trend years ago, though; instead, this Mini has a black coat with red racing stripes down the middle.
12 Jaguar F-Type
The cars Hefner and his publication Playboy gave out to its top models all varied in brand and style. According to USA Today, Raquel Pomplun received a Jaguar F-Type. She beamed while posing next to the car at the Playboy Mansion when they awarded her with it.
Jaguars may not have a reputation for their reliability or ability to stand the test of time, yet they excel in luxury. Not to mention, they look stylish, too. One could argue that having looks is the most important criteria for any car that shows up and parks in Hefner’s garage at the Playboy Mansion.
11 Mercedes-Benz 600 Pullman
What do Hugh Hefner and Pablo Escobar’s car collection have in common? They both included Mercedes-Benz 600 Pullmans. These limos represent luxury, class, and status all in one. According to Top Speed, the 600 went into production in 1963 and ended in 1981.
That’s a healthy run for this opulent automobile that high-profile people are attracted to. The Drive reports that this limo was part of Hefner’s rich collection of automobiles to gad around town in. With Hefner having a Mercedes-Benz like this, no one doubted his fortune or his stature as one of the world's biggest magazine moguls.
10 Chevrolet Corvette C4
This Corvette will make car enthusiasts jealous. According to AutoGuide, Donna Edmondson won the car from Playboy as the top model in 1987. The same source reports that the Corvette went through a 1984 makeover, which is reflected in this particular Playboy version as well. With its red paint job, it looks like a race car straight out of an ‘80s arcade game.
Of the cars given out to Playboy models, this one doesn’t sport the characteristic pink paint. AutoGuide points out that the car started at around $28,000, making this one generous giveaway. If Hefner really wanted to, though, he had enough money to fill his garage with Corvettes.
9 Chevrolet Barrister Corvette
It may not be a car Hugh Hefner owned himself, although it certainly found its way to the Playboy Mansion on several occasions. Owned by legendary Hollywood actor James Caan, this Barrister was something fierce with its numerous exhaust pipes curling up out the sides.
According to Motor1, those pipes once belonged to a church organ. Whoever played that church organ probably never imagined those pipes would go on a Corvette, let alone one that frequented the Playboy Mansion. The source also adds that the headlamps came from a Ford Granada, proving once again that this car is something of a Frankenstein monster.
8 Sunbeam Tiger
If Playboy models got the top honors for the year, the popular periodical didn’t hesitate to recognize its stars. Hefner could fill his garage with any car imaginable. Instead of greedily holding on to them, though, he awarded the magazine's best employees. The prizes even included limited-edition versions like this Sunbeam Tiger. According to AutoGuide, there are only 633 of these cars in existence.
Small, classy, and, of course, pink—Jo Collins was the lucky recipient of Playboy’s special edition Sunbeam Tiger. The same source reports that this Sunbeam Tiger was another addition from racecar extraordinaire Carroll Shelby, making it that much more legendary.
7 Ford Mustang
Only a handful of cars are capable of stirring up enthusiasm among aficionados and amateurs alike. One of those has to be Ford Mustangs, which have had one of the most storied legacies in automobile history. It’s only fitting that Playboy’s top model in 1963 got one in turn.
According to AutoGuide, Donna Michelle got a pink Ford Mustang that, back in its day, was worth only $2,814. By today’s standards, that’s nothing. However, when one adjusts for inflation using online calculators, that price tag can amount to somewhere slightly north of $20,000, making this an impressive trophy.
6 BMW 3.0CS E9
The history between Playboy and the automobile industry goes back years. According to The Drive, Playboy put on racing shows that helped solidify Hefner’s passion for cars and speed. There was also another aspect to his love for cars: luxury. Being comfortable and looking cool were important to Hefner's driving experience.
His 1972 BMW 3.0CS E9 helped satisfy those criteria he established for himself. This RWD coupe not only provided Hefner with a pleasant driving experience but also injected a slight boost in performance to his daily routine. It may not be the finest car to arrive at the Playboy Mansion in, but it’s significant nonetheless.
5 Porsche 911S
It’s the kind of Porsche many would take without hesitation in spite of the pink paint job. Awarded to Playboy’s top model in 1975, AutoGuide reports that Marilyn Lange received this special Porsche that didn't slack off when it came to performance. The same source goes on to detail what’s under the hood: an impressive 2.7-liter V6 that can deliver 173 hp.
With the technical mastery and handling Porsches are often known for, it’s easy to imagine this zipping down winding roads. The only thing discouraging such brisk excursions is the pink color, which will attract cops from a mile away.
4 Plymouth Road Runner
The Playboy Mansion has paid host to some of the coolest cars around. Like the celebrities and high-profile figures who visit the Mansion, illustrious and classic cars have also dropped in. According to Motoropia, the Playboy Mansion hosted a show put on by Mopar Collector’s Guide Magazine in 2008.
A 1937 Plymouth Road Runner painted in green made an appearance. The same source reports that it can deliver an insane 930 hp, which makes this modified creation more monster than machine. More than likely, it stopped by Hefner’s garage for a tune-up and rest before continuing on its travels.
3 Dodge Charger
When it comes to muscle cars, the Dodge Charger is one many enthusiasts put in their list of top ten favorites. Although many would argue it’s more a sedan now than a muscle car, Dodge is still making and improving them today. AutoGuide notes that Allison Parks got one back in 1965 for being Playboy’s top model of the year.
This special version came with a powerful V8 engine. It cost a little more than some of the others on the list, and AutoGuide puts the price of the vehicle at a little more than $3,000. That may not sound like a lot by today’s standards, but it’s impressive for the mid-1960s.
2 Porsche Boxster
It’s not the first Porsche to appear on this list—and it’s not pink either—but it’s one Playboy gave out. According to the Boston Herald, this Porsche Boxster went to Victoria Silvstedt around 25 years ago, back in 1997.
Silvstedt lucked out with this speedy convertible that Cars.com details has a 2.5-liter engine that can deliver 202 hp. While the performance may not get the highest marks, the exterior looks stylish. It’s the perfect car to make an impression and one that remains consistent with all of Hefner’s cars he either kept or gave away.
1 Shelby GT500
Look at the scoops on the hood of this rad car. This vehicle is special in more ways than just design, however. AutoGuide reports that it can go from 0 to 60 mph in just six seconds. The Shelby name is one with a rich and storied legacy within automobile history.
It’s something that’s become synonymous with muscle cars and their high performance. Even more, out of the same source, only a limited number of these exist. There have been just a little more than 1,500 ever produced. Plus, this Playboy edition came in a lighter pink than others.
Sources: CNBC, The Drive, Top Speed, AutoGuide, Top Speed, The Drive