Today, Mark Cuban is one of the richest people in the world. But when he was younger, that wasn’t the case. As his wealth has improved over the years, so have his rides.

Although it took him a while to invest in his first nice vehicle. From his first car, that cost less than $200, to the million-dollar limo he drives today, take a look at Mark Cuban’s automobile history.

Humble beginnings with the 1966 Buick LeSabre and Fiat X1/9

The 1966 Buick LeSabre is one of the many cars Cuban drove before he was 25 years old. Just like every car during that time, this clunker cost under $200 and wasn’t much to look at. Even though he had money in his early twenties, he chose to keep his car expenses low because of a money-making philosophy of living well below one’s means and investing the rest. In addition to the Buick, he also had a Fiat X1/9 with a hole in the floorboard.

Although neither of these cars was pretty, they were reliable, which Cuban states is all he needed in a car at that time. He accredits much of his fortune to this time in his life when he drove cheap cars, lived with roommates, and made macaroni and cheese every day in an effort to invest. 

Mercedes-Benz S600 Pullman Guard

In addition to buying nice cars for himself, Cuban is a family man. He was spotted driving himself and his family off the set of Shark Tank, the hit NBC show where he gained much of his fame as an investor, in a Mercedes-Benz S600 Pullman Guard limousine. The Guard is no joke; its primary responsibility is to keep celebrities safe, sporting bulletproof tires, all-around armoring, and a steel bulkhead to protect the driver’s neck in case of attack. 

With all of this armoring and safety equipment, the Guard weighs 11,200 pounds and takes a year and a half to go from order to delivery. It’s incredibly exclusive to even order, and very few people can afford to own it in the first place.

The car is worth $1.56 million in 2019, making it the most expensive Mercedes-Benz on the market today and a far cry from Cuban’s $200 beginnings.  

Finding the 1955 Ford Customline 

One of Cuban’s most unique cars is the 1955 Ford Customline that he bought in 2013. The backstory behind this car is different than the others, though; to find this ride, he went on reality TV show Fast N’ Loud and had the Gas Monkey garage crew find him the perfect car. His requirements? “An ‘Oh my goodness!’ cruiser.”

This Ford vehicle certainly fits, with a sleek white exterior paint, an all-green interior, and a vintage fender that is sure to turn heads. The vehicle was initially a museum piece that was restored, but the tires are still the original.

Cuban has a documented interest in vintage cars like this Ford, even telling the Gas Monkey crew that he wanted an extremely old-fashioned rather than modern look.

Although Mark Cuban is a billionaire, that has never stopped him from living a relatively normal life when he drives his cars. He’s even gone on record saying one of his favorite pastimes is blasting embarrassing old-school hip-hop music when he drives his daughter to school and watching her “bury her head” in embarrassment.

No matter which car he’s driving, Mark Cuban is a smart investor and a family man who has always made thoughtful choices when it comes to his rides. What do you think of Cuban’s rides? Share your thoughts in the comments below!