Befitting a man of renowned appetites, Mr Hefner owned a good many cars in his lifetime but was synonymous with none quite so much as the Mercedes-Benz 600 - specifically the long-wheelbase Pullman.
He was not alone in his affections. During its heyday, the 600 also bestrode the driveways of Coco Chanel, Elizabeth Taylor, John Lennon, Jack Nicholson, Ronnie Wood and Elvis Presley - not to mention the garages of Pol Pot, Nicolae Ceausescu, Idi Amin and Leonid Brezhnev. As a signifier of 60s-era wealth and power, its pedigree is unmatched.
Of course, Mr Hefner likely favoured a chauffeur-driven Pullman for its prodigious size; the car's 20-foot length permitting a very generous amount of space for, erm... reclining. Its no-expense-spared development also made it a much lauded benchmark for rolling refinement and high-end convenience.
Much of this reputation was owed to the 600's bespoke hydraulic system, which powered everything from the door locks to the suspension damping. Running on mineral oil at the sort of pressure normally used to cut through concrete, the technology was selected for its speediness and near silent operation. That it contributed mightily to the model's titanic kerbweight and fiscally eye-watering breakdown potential hardly mattered.
Naturally a hydraulic setup of such elaborate scale needed to be powered by something equally extravagant, and having discovered that its contemporary 3.0-litre inline six-pot wasn't really up to the task, Mercedes opted to develop a V8, resulting in the idiosyncratic splendour of the 6.3-litre V8 - or, as its better known, the M100.
Hand-built, and including novel features like sodium-filled valves, forged components, dual alternators and a mechanical fuel injection system, the V8 produced 250hp and - according to our advertiser - 434lb ft of torque from 3,000rpm.
We'd be tempted to quibble with that figure slightly - but such is the gloriousness of the car up for sale that we'll keep our statistic to ourselves and simply marvel instead at the restoration job done on this immaculate 1972 example, on sale for £395K. Mr Hefner was already 46 by that year, and a millionaire many times over. Ideal conditions then for tan velour and a full body shellacking of chocolate brown. RIP, bon vivant.
MERCEDES-BENZ 600 PULLMAN
Engine: 6,329cc, V8
Tranmission: 4-speed automatic, rear-wheel drive
Power (hp): 250@4,000rpm
Torque (lb ft): 370@2,800rpm
MPG: N/A
CO2: N/A
First registered: N/A
Recorded mileage: N/A
Price new: N/A
Yours for: £395,000
See the original advert here.