The Mille Miglia should be on any gearhead's bucket list. While today's event is merely an homage to the original race that ran each year from 1927 to 1957—stopping only for the second World War—it's still a race of impossible romance and deep appeal.

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If you're Jay Leno, it's even better—since companies like Jaguar invite you to compete in immaculately-prepared examples of cars that ran the original race. Partnered with Jaguar design boss Ian Callum, Leno's chariot for the 2014 Mille Miglia was an XK120 in famous Ecurie Ecosse livery. Callum and Leno weren't alone either—fellow Jaguar pilots included former F1 drivers Bruno Senna and Martin Brundle in a D-Type, model and TV presenter Jodie Kidd, and AC/DC rocker Brian Johnson. The rest of the race is awash with 'gullwing' Mercedes-Benzes, Lancias of every kind, Bentleys, Alfa Romeos and more—not just on display, but driven hard through Italy's picturesque towns and countryside.

The Mille Miglia route runs from Brescia in the north of the country to the capital Rome, about half way down—and back again. Back in the 1950s, Stirling Moss set the race's all-time record, covering the thousand-mile run with an average speed of more than 100 mph. Moss himself reveals some of the race's quirks in Leno's latest video, from weaving on straights to encourage spectators to stand back, to his banana-only diet—necessitated by the difficulty of eating anything else while driving.

Leno and Callum had it a little easier, and today's event is more of a regularity rally than an outright race. But timing is still tough, and the roads full of traffic, so today's homage remains a thrilling and sometimes dangerous race—as illustrated by the destruction of a 1956 300 SL at this year's event. Others escaped lightly, and for those that finish the event there can be few better feelings—long may events like the Mille Miglia continue.

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