These Are Racing Drivers Who Had The Coolest Careers

(As a second to Andretti) Dan Gurney

Raced in F1 for many teams; built, raced, and won with his own car (the Weslake-Eagle, IMO the most beautiful car of all time); raced Indy, NASCAR, SCCA, Trans-Am, and LeMans; team owner; and won the inaugural Cannonball Run.

Pretty cool, indeed.

Jacky Ickx.

6x Le Mans winner, Paris-Dakar winner, Can Am champ, and a pretty decent F1 career and finished 2nd in the standings in 1969 and 1970. And he’s just a cool guy.

Aussie V8 Supercar driver Peter Brock - not necessarily the coolest but certainly the funniest what with somehow convincing GM to sell a car “enhanced” by magical crystals.

The episode of The Dollop about Peter Brock is hilarious.

My favorite would have to be Alex Zanardi, I loved how he bounced around F1 and CART in the US, and it thrilled me when he’d win here in CART and do smoking donuts after a victory. Also how later in life he had a horrific accident that required amputation, to which he still kept racing in all kinds of racing styles.

Paul Newman.

He came to the sport later in his career but he left a mark on the industry and there is no denying the fact that he was an absolute car fanatic.

Runner up: James Garner. Not exactly a professional racer but surely a gearhead and driver.

Phil Hill

Let’s first just look at the man’s credentials:

24 Hours of Le Mans (3) : 1958, 1961, 1962
12 Hours of Sebring (4) : 1955 (3.0 class), 1958, 1959, 1961
1000 km Buenos Aires (3) : 1956 (S+3.0 class), 1958, 1960
1000 km Nürburgring (2) : 1962, 1966
F1 Italian Grand Prix (2) : 1960, 1961
F1 Belgian Grand Prix (1) : 1961
BOAC 500 (Brands Hatch) (1) : 1967
Targa Florio (1) : 1960 (3.0 class)
Road America 500 (2) : 1955, 1957
Continental Tire Monterey Grand Prix (3) : 1950, 1953, 1955
Los Angeles Times Grand Prix (1) : 1959
Swedish Grand Prix (1) : 1956
2000 km Daytona (1) : 1964

Yes, not only was he the first American to win the F1 Championship and Le Mans, but then went on to win Le Mans 2 more times!

Had a successful run working for Enzo, then went and beat Ferrari while driving both the Ford GT40s as well as Jim Hall’s Infamous Chaparral.

Hill has the distinction of having won the first (a three-lap event at Carrell Speedway in a MG TC on July 24, 1949) and last races of his driving career, the final victory driving for Chaparral in the BOAC 500 at Brands Hatch in England in 1967.

Once he retired, cars were still his life. He started a restoration company. Commented for ABC’s Wide World of Sports racing telecasts, and has voted more times as a judge in the Pebble Beach Concours d’Elegance, then anyone else in history. (40 times!)

He actually was rushed to the hospital from a car show. After traveling to the Monterey Historic Automobile Races in August 2008, Hill was taken to Community Hospital of the Monterey Peninsula, where he passed away at the age of 81.

He not only raced in the golden era, but raced for just about every major player at the time. Ferrari, Ford, Shelby America, Jim Hall, and countless others.

Dude, literally saw and did it all!

Honorable mention to John Surtees for being the only one to win both the FIM 500cc Moto GP and FIA Formula driver’s title.

Also Steve McQueen never one much but raced anything he could

Never won anything big (and apparently a jerk), but i always thought robby gordon had a pretty fascinating career.

“Real” answer is probably a driver that pre-dates not being allowed to race all over the place because of things like sponsor conflict, packed calendar for their primary series, contractually not being allowed to do unsafe hobbies, etc.

Leon Duray, aka George Stewart.

Sat on the pole a couple times at Indy during the 1920s. Raced on board and dirt tracks. Took several Miller race cars to Europe where he set Grand Prix speed records but never won a race. So, always fast, but always broke the fragile machines, just like he did in US racing. Sold and traded his Millers to Ettore Bugatti, who copied the engine design to a large extent.

Lived 62 years, which given his life at speed, was quite an accomplishment.

...And in 1969, a fellow named Leon Duray, aka “Jigger” Sirois, drove fast enough for the pole at Indianapolis, but his attempt was waved off and he never raced in the 500. (He’s still kicking too!)

So, people named Leon Duray have had the coolest unheralded racing careers!

I’d say Emerson Fittipaldi, he won two F1 drivers championchips, two Indy 500's and a CART title. He also managed to upset the status quo by chugging orange juice on the podium when he took the checkered flag at Indianapolis.

It is hard to argue that Mario Andretti does not belong on the short list in this category and, of course, this type of discussion can never come up with a definitive answer. I would suggest that one should look a little farther back in time for drivers with “cool” careers.

This is an example of the types of drivers that one could come across in relatively “small” events. F1, USAC (Indy car), SCCA, etc., drivers would compete in a wide variety of cars. Later in the 1960s, Can-AM and Trans-Am, (definitely big-time) races would draw top-level racers from across the world. A little research would probably show that many NASCAR drivers of that era also had fascinating careers. For me, some of the most interesting tidbits are stories about the era are Bruce Mclaren, Stirling Moss, etc., driving Austin-Healey Sprites at Sebring.

It is worth noting that Roger Penske had a relatively short, but interesting, career as a driver in that era.

There are great drivers in every era and many of them have cool careers but, nowadays, their careers seem to be a bit more specialized and, I think, slightly less interesting.