I usually associate beautiful old cars with musty warehouses or garages that have a lingering smell of gasoline, the kind of place where work is done and work is completed. RM Sotheby’s has performed the remarkable trick of shaking this association entirely out of my mind.

Car reviews are fine, but oftentimes, very limited. What can you really learn from an afternoon with a car or during a very controlled track experience?

Everyone asks the 84-year-old about his art. Instead, we asked him about cars. Turns out, he’s a closet hot rod lover (and a whole lot more).

We chat supercars and Bentleys with the tennis demigod and her pal, Chelsea Handler. Then, try to return a Sharapova serve. That last bit turned out exactly how you’d expect.

Here’s the evening plan: Drive to that new Italian spot, maybe a nice bottle of Nebbiolo; wheel over to your favorite cocktail joint, where the bartender makes a mean Negroni. Now everyone’s lit and happy, but the buds need a ride home. No, really, I got this. Climb aboard.

Gianni Agnelli was everything you’d want the Chairman of an Italian car company to be. A style icon, one who’d been shot in a dive bar by a Nazi officer during an argument over a girl; an international playboy who raced yachts with John F. Kennedy; and, of course, the heir to Italy’s largest company.

Some trucks just wanna have fun—even if just for one season. It’s as if Land Rover cobbled a segment together from every eBay pull-down menu.

A giddy group of tech journalists nervously shift their weight, fidgeting some. Zac Moseley, owner of Classic Car Club Manhattan (CCC), is giving his “how-to-not-wreck-our-supercars” speech. We’re about to set off on a drive with four exceptional vehicles to test a small plastic box that aims to unlock the full…