1928 Cadillac Town Sedan
The official car of Al Capone, its paltry 90 horsepower seems feeble by today's standards, especially when you factor in the mobster's bespoke additions: 3,000 pounds of steel and thick glass, which brought this early exercise in home armoring in at 9,000 lbs in its stocking feet. And it was smartly painted green and black to blend in with the Caddies owned by the City of Chicago—because it sure wasn't outrunning much.
Rolls Royce Silver Ghost (1907-1926)
If you think owning a Roller is a big deal today, imagine the infamous 1920s bootlegger Enoch "Nucky" Johnson (now of "Boardwalk Empire" fame), whose reported $500,000 yearly take on illegal booze sales floated him one of the last of the original Silver Ghosts—at a cost of $14,000, or the price of almost 50 new Model Ts. Considering that any punk with a few grand can rent a Phantom for a day now, we have here proof that social mobility has come a way since Prohibition and the Roaring Twenties. It has, hasn't it?
1929 Bentley 4½ Litre "Blower"
Though he'd not run afoul of English law, Woolf Barnato's fortune stemmed from the diamond trade (his father's firm became part of DeBeers's infamous cartel), a business arguably more destructive than rum running or hooking. While England's working classes stayed poor and Apartheid South Africa profited the few, Barnato and his crew, the Bentley Boys, spent their profligate days far, far away from the site of their shame, except when they were racing about (even against locomotives) in their Bentley motorcars. Doing good while doing badly, Barnato served as the unofficial patron of Bentley through the 1920s, but the Depression forced him to sell out to Rolls-Royce in 1931. The so-called Blower Bentleys were riddled with problems both on and off the track, but if you were a well-heeled rogue in the pre WWII era, this was the steed you needed.
Ford Model 18 "V-8" (1932-1934)
The world's first accessibly priced V-8, introduced by Ford in 1932, it was instantly memorialized by diverse miscreants on the lam, but especially by bank robbers John Dillinger and the Barrows (Bonnie and Clyde), who each wrote to Henry Ford thanking him from a criminal's perspective for his innovation. With its iconic "flathead" design, the Ford V-8 brought accessible power to thieves on the go. Another no-goodnik, Baby Face Nelson, liked them so much he would, along with Dillinger and the Barrows, wind up dying near one
Citroën Traction Avant (1934-1957)
With one of the first successful applications of front-wheel drive, and among the world's first monocoque bodies, the Citroën Traction Avant makes most everyone's list of significant cars, but it's here for a more ignominious reason—it became a quick favorite of the Gestapo in Occupied France, remaining as well the default choice of Gallic organized crime, who liked the low-slung Citroën's forgiving ride and superior handling. Indeed, the car was so advanced for its time that it actually drove Citroën to bankruptcy in 1934 (founder Andre Citroën died the following year), and ownership by tire giant Michelin ensued. That's not criminal, though—that's capitalism.
Mercury Eight (1946-1951)
With most automobile production halted in America during World War II, the return of the Mercury Eight ushered in a bold new era. Powered by the Mercury L-head V-8 (à la the Ford L-head V-8) but lower, longer, and meaner than its Ford counterparts, it became the car of choice not just for scammers and stick-up guys but for outrageous custom car builders like George Barris and others, who'd stick a finger in the eye of prevailing cultural values of the time—James Dean drove one in Rebel Without A Cause, and that's you all you need to know.
Jaguar MK VII-IX (1951-1960)
Stateside, Jaguar was best known for swoopy sports cars, but across the pond, the firm's voluptuous four-door sedans—whose 6-cylinder engines the XK sportsters had been designed to showcase—quickly acquired the underworld's seal of approval. Winning the Monte Carlo Rally with a top speed around 100 mph, the Mark VII and successive iterations were fast, capacious and loud (as in just this side of vulgar), making them a preferred ride for the Brothers Kray and a generation of British criminals
Chevrolet Impala (1963-1964)
In its day, the Impala was an everyman's car, with an audience ranging from hard-working family men with crew cuts to civil rights workers to country-clubbers with Republican party memberships to grifters, pimps and con artists. How fitting then that decades later the Six-Four Impala remained an ubiquitous icon, appealing to both South Central gangbangers and drug-dealing Chicano lowriders, at a time when the main thing they had in common was a mutual enthusiasm for women with Kardashian-sized rears. Watch any West Coast rap video from practically any era and you're bound to see one. Go to any Sunday American Legion game in Middle America, and you'll find one there, too. The wifebeater won't be far off.
Ford Lotus Cortina (1963-1966)
Jim Clark. Graham Hill. Colin Chapman. Car enthusiasts will recognize these famous names associated with the Lotus Cortina, but here's another one you should know: Bruce Reynolds, the mastermind behind the Great Train Robbery, a heist which saw thieves make off with the equivalent of $7 million in used bank notes in Britain's largest robbery to that date, back in 1963 when $7 million really was $7 million. While Reynolds and his gang ended up using Land Rovers to haul the cash, his own Lotus Cortina was famously used for reconnaissance. When it was go time, we suspect, the flashy white and green paint scheme was a little too conspicuous.
Jaguar XJ (1969-1987)
If the Mark VII Jag is a car Michael Caine might have driven around East London in the underworld cinema of yore, then the XJ would be the ride of choice for the bumbling, shearling-clad henchmen of more recent Guy Ritchie outings. Sure, the '70s and '80s constituted a dorky interlude for the entire auto industry, and Jaguar's build-quality trangressions were never more evident. But the classic styling and engineering briefs laid out by the XJ would, along with epic depreciation, help to usher it on its way for a preternaturally long run down in the street-level world of hoodlums who'll pay any price for a little class, as long as that price is not much.
Lincoln Continental Mark III-VIII (1969-1998)
What's the point of being a successful criminal if you can't flaunt your wealth with a loud and proud display of good ol'-fashioned bad taste? The older Sicillian mobsters of "Donnie Brasco" might have dismissed the Lincoln Continental over comparable Cadillac Eldorados, but Lincoln's baroque personal luxury coupe, with its acres of prow, vestigial spare tire hump, and propensity for hideous, vinyl "landau" half-roofs replete with opera windows, was always the big-pimping alternative. A stylistic departure from the coolly elegant, four-door Continentals of the 1960s, the Conti coupes were the ostentatious, menacing symbols of Cosa Nostra big earners through four decades. Insert outsized funeral wreath here: RIP, Continental Mark.
Mercury Marquis (1967-1974)
Back in the day, it seemed like every cop show ("The Streets of San Francisco," "Cannon," "Hawaii Five-O," "Starsky and Hutch") featured a baddie driving one of these FoMoCo barges. Anonymous yet with overtones of evil, they ticked all the boxes in that they looked grim, and had plenty of room for perps, automatic weapons, contraband, and dead guys. It was only when they cornered hard in chase scenes—squealing and kneeling on their soft, bias-ply whitewalls and understeering like ocean liners, that you realized that choosing machinery like this, the criminal classes weren't always as bright as they were malevolent. To be fair, the lawmen often drove the same hopeless sedans, underscoring the enduring psychological truth: Sometimes all that separates criminals from cops is the color of their Mercury.
Lamborghini Countach (1974-1990)
Many an adolescent boy had the white Countach poster on their bedroom wall, but a few lucky "commodities traders" in South Beach had the real thing along with all the trappings said teenage boys dreamed of, like a mobile phone, gold Rolex, and artificially enhanced girlfriend. The 12-cylinder Countach was a ludicrously impractical car with little to redeem it beyond aesthetics, but the machine remains infamous and so evocative of the decadence of the '80s that it's a first-ballot immortal from the era's criminal motor pool. Usually finished in garish psychedelic hues, a matte-black example, painted in radar-resistant stealth-bomber paint, is rumored to have had a successful if short-lived career running drugs between Miami and New York .
Porsche 911 Turbo (1974-1989)
If the Countach was the sports car for people who dealt only in cash, the boosted 911 was for people who didn't make money ethically but still filed a tax return. The 930 Turbo (as its known among Porschephiles) was nicknamed "the lawyer killer" for its propensity to wrap itself around trees when its operator caught a nasty wave of panic-induced lift-off oversteer. The Porsche Turbo available today has seen the rough edges removed and is a far cry from its savage ancestor, which was the living embodiment of the fuck-you money its owners helped themselves to.
Mercedes Benz S-Class (1991-1999)
For a time, one could make the case that the W140 S-Class was the best car in the world, but its psychological impact may have been eternal. Marking the cusp before Mercedes's shift from vault-like solidity to over-technological unreliability, this brickiest of brick-house S-Classes was a battle cruiser par excellence, finding favor with captains of industry and criminals—organized and disorganized—as well as a growing band of gangsta rappers, the self-proclaimed criminals whose sales grew in direct proportion to how often they were vilified by the media that underwrote them. Puff Daddy made the big-body Benz the ride of choice for youthful hood denizens back in the '90s, and since these big old S-Classes rarely die of natural causes, that legacy endures.
Lincoln Navigator (1998-present)
Even before the Escalade and quite unlike the upward-mobility time-traveler Range Rover, the Navigator was the original luxury SUV for the made man, combining heft, aggression and less than tasteful luxury cues in a package that strongly appealed to the well-heeled thug's practical side as well as his underlying reptilian sensibility. With all the utilitarian appeal of an SUV, plus the price tag and chrome-tastic flashiness of a luxury car, it didn't take long for automakers to rally around the genre and the absurd profit markups that could be generated. Like any criminal enterprise, the whole scheme came crashing down when fortunes reversed, but just think where we'd be without luxury SUVs.
Cadillac Escalade (1999-present)
So ubiquitous and sinister-looking that its name alone conjures images of shady enterprises and disreputable characters, the Escalade vanquished its Lincoln rival and took its place alongside the S-Class as THE ride of choice for those on the sales end of the urban pharmaceutical business. In a sense, the car almost got too popular for its own good, and as used examples started trickling down to the underclasses, Reaganomics style, they came within reach of even the lowliest dirtbag bounders. As a young friend cogently observed, "When people like The Situation start jocking your swag, you know its time to move on."
Maybach 57/62 (2003-present)
The Maybach was created in part because the S-Class had started suffering a similar problem to Escalade—it was too accessible and hence over-exposed. The solution evidently was to take an even older S-Class chassis, make it look like a Hyundai while bloating it in evey direction, and then sell it for exponentially more. While it quickly became a favorite of third world dictators, record executives, and Wall Street robber barrons, it never achieved the sales figures Mercedes had hoped—even the deeply cynical get it wrong sometimes. Nevertheless, infamously profligate media mogul Birdman recently added a 62 Landaulet model (estimated price: $1.45 million) to his collection, where it joins his similarly introvert Bugatti Veyron. Only in America...
Ferrari F360/F430 (1999-2009)
You'd think that your brightest criminal minds would appreciate the advantages of discreet transport and low depreciation, but no. We left off Ferrari's cash-incinerating Testarossa from our '80s segment because the Countach is arguably the more iconic Italian exotic, but in the 2000s, the F360 and its niftier F430 follow-up ruled the roost. Lamborghini's Gallardo lacked the marque's trademark swing-up doors, but the first 21st century Ferrari was all Ferrari, with carnal styling and an exhaust note that could be heard for miles. The F1 paddle-shift transmission meant clutchless shifting via steering wheel controls, and the ability to snort coke bumps off the hand-stitched center console. Clearly, some criminals just want to go out in a blaze of glory. Top of the world, Ma.
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