From the Sicilian Mafia to the Japanese Yakuza.
The general public has always had a fascination with the underbelly of society, and organized gangs glue it together. Gangsters all over the world need general transport, and whether we talk about street gangs or the Italian mafia, gangster cars serve as status symbols first and practical vehicles second. Part of that status is telling people the owner has power through money, force, or both. Practicality generally comes with size and power. Some cars have become closely associated with organized crime and gangsters to be used as shorthand in movies. A black Range Rover is a prime global example, and that's where we'll start.
Whether it's Mexican cartels, LA gangbangers, or European villains, a black Range Rover is a prime and general example of gangster or gangsta cars. It's as iconic in movies as it is on the street. One of the most famous specific examples is a gritty one in the UK known as the Range Rover Murders.
Craig Rolfe, Tony Tucker, and Pat Tate were three notorious drug dealers in Essex and part of the "Essex Boys" gang, to the point this writer remembers seeing them around and serving one of them in a gas station way back in the day. They were found in a shotgun-blasted Range Rover down a lane they were lured to near a busy road.
The Range Rover achieved its gangster association by being big, comfortable, powerful, and expensive - which are traits in most of the cars on this list and able to go off-road easily. Hence, it's particularly popular with Cartels and British gangs, but its appeal is just as apparent with urban gangsters.
The most famous of the mobster cars is the Lincoln Continental. Whatever the classic decade, the Lincoln Continental conveyed wealth and style while having a menacing look about it. Part of that menacing look could be that you can fit at least two bodies in the trunk. Paul Castellano, head of the Gambino crime family, drove a Continental. John Gotti, who ordered Castellano's death and became boss of the Gambino family, also owned one. To get an idea of how desirable the luxury car was at the peak of the Mafia's hold over New York, Richard Kuklinski, a Mafia contract killer, spoke in his book about wanting to own one from an early age. In popular culture, it's one of the great old-school gangster cars and is ingrained into our consciousness from movies such as The Godfather and Goodfellas. Because of the, the Continental is one the definitive mob cars.
Rarely is the Mercedes S-Class depicted as a mobster car in movies, but it is the car to drive if you're up the chain of command in the Japanese Yakuza. Curiously, they nearly always have tinted windows and are left-hand-drive in a country where right-hand-drive is the norm. The Mercedes S-Class is chosen for the same reason it's popular everywhere else for the well-heeled - it's stylish, luxurious, powerful, and reliable. The tinted windows are logical because gangsters live in a world where discreation and secrecy is important and violence is normal. The left hand drive is a question of status, and not only in Yakuza circles. It's a Japanese society thing.
If you were in the Mafia in the 1940s and 1950s, there was no more of an intimidating luxury car than the 1937 Mercedes Benz 260D. Its original infamy came from its use by the Nazi SS death squads during World War II when it became known as the Death Car. However, it's equally, if not more readily, identifiable from pop culture as one of the original Italian mafia cars. Only 1,967 were built after the war, so it was rare as well. If you saw one of these rolling through Sicily back in the day, you knew that whoever was inside was a big deal and not to be trifled with.
While we're on the subject of old gangster cars, the Ford Model 18 V8 was a favorite amongst gangsters as it was a powerful getaway car. The most famous photos of a 1932 Ford Model 18 V8 feature a lot of bullet holes and the dead bodies of Bonnie and Clyde, but technically they were just criminals, not gangsters. The most famous gangster that favored the Model 18 was John Dillinger. He was a gangster during the Great Depression that caught the media's attention, and Dillinger played up to it. Conversely, J. Edgar Hoover used that media fame to evolve the Bureau of Investigation into the Federal Bureau of Investigation (FBI). With the Dillinger Gang, he is known to have been part of at least 12 bank robberies over two years. His most famous escapade was escaping from a jail in Indiana that the police boasted as being "escape-proof."
When it comes to classic gangster cars, the Brits love a Jaguar. The Jaguar Mark II was famous for being used in bank robberies in the early 1960s. It turned out that 'grace, space, and pace' was a great slogan to advertise to criminals as well as the general well-to-do. However, they were often stolen cars. If you were a real gangster, like the Kray brothers, you drove a Jaguar MK X. The MK X was designed with the US market in mind, so it was one of the widest cars on the market. It also came with the legendary XK straight-six engine. The Kray twins are the most infamous gangsters in the UK, and their gang, known simply as the Firm, pretty much owned the East End of London through the 1950s and 1960s. Towards the end of their reign of terror, the MK X was their ride of choice. There are other 1960s gangster cars, but the MK X was the biggest statement that could be made, as Rolls-Royces were for pop stars and posers.
Russian mobster cars are generally varied, but the BMW 7 Series is a staple for those higher up the ranks. The G-Wagon is often associated with Eastern European gangs, but they're not particularly maneuverable and are mostly driven by bodyguards or soldiers. The 7 Series has the same advantages of power and handling that the 5 Series delivers, but with more space and luxury amenities. It also draws about as much attention as a BMW 5 Series, and in the ultra-violent world of the Russian Mafia, being discrete is how you gain power and hold onto it.
Whether you know him as Al Capone or Scarface, he's the most famous gangster of all time. He was an antiques dealer that became a Chicago-based bootlegger during prohibition. He's become the subject of endless books and movies and owned cars that suited his ego. The most famous of those is the 1928 V8-powered Cadillac that he had armored with almost 3,000 pounds of steel plating. Later on, bullet-resistant windows were added, and it was painted green with black fenders to look like a police car of its period. It's one of the most famous mobster cars and was last seen up for sale for a million dollars.
It's big, it's expensive, it's powerful, and it can go off-road. The Cadillac Escalade is the brash partner to the Range Rover. It's a statement car that exudes power and money, and is a good choice for gangsters that don't want to keep a low profile. That makes it popular for downtown-based gangsters that want to be seen on the streets and either remind people who's in control or just brag that they have money and power - even if it's just an older model and they control a single neighborhood. Further up the pole, the real money-makers can go new and have their Cadillacs armored. Just like Capone.