Jay takes boxing royalty Sugar Ray Leonard for a stroll down memory lane, before letting him take his own swing at a regal Rolls Royce Corniche; he trades jabs with Goodfella and Sinatra fanboy Ray Liotta in a 1961 Dual Ghia.

Rapper Rick Ross brings both the heat and smoke in a Hellcat burnout challenge; Fluffy aka Gabriel Iglesias and Jay attempt to move heaven and earth during a CrossFit challenge in a colossal pair of Caterpillar excavators.

Jay meets up with Cedric the Entertainer, who can’t get enough love from Barry White’s bawlin’ 1977 Stutz Blackhawk 6. Then Jay expands the vocabulary of Sebastion Maniscalco who definitely takes a shine to a hot to trot, 1949 Hudson Derelict.

Jay and talk show phenom Trevor Noah test-drive the lightning-fast, all-new, all-electric Mercedes EQS. Then Jay does his damnedest to demolish the already ludicrous world record for the fastest production vehicle ever in Tesla’s all-new Model S Plaid. After attempting to rewrite history, Jay squeezes Comedian Tom Segura into a bug-size Bugatti, lets loose in a one-of-a-kind Porsche Carrera Coupe, and rides off into the sunset with actor Balthazar Getty in a ridiculously rare Lamborghini Sian.

Jay finds out if he can win his cupcakes and eat them too, while off-road racing American Idol Kelly Clarkson in the mother of all minivans; Jay gets an exclusive first look at the ultimate eco-friendly off-roader: the all-new, all-electric Hummer.

Jay Leno kicks Drew Carey's soccer dreams into high gear; James Corden tries to steal Jay's Jag; Jay and Gary Sinise salute a decorated veteran who's helping other vets achieve their dreams; Tammy Pescatelli may be the first to crash car.

Jay and Tim Allen go helmet to helmet in an otherworldly shuttle-van Space Race. Brad Garrett learns how to pedal his way across the finish line. Brad Paisley trades his donkey for an all-new 2021 Corvette C8.

Mark Cuban sinks his shark teeth into a classic Cadillac El Dorado convertible. Jay puts only one degree of separation between Kevin Bacon and the all-new Ford Bronco.

Get ready to roll up your sleeves and Gritter Done! Jay will take the hilarious Tiffany Haddish on the ride of her automotive life and we'll see just how high she pulled herself up by her bootstraps! Then Jay lets big time funnyman Bert Kresicher out of his trunk to find out how he went from life of the party to one of the biggest comedy act in the world! Next up, Ford CEO Jim Farley made didn't follow in the footsteps of some other famous Farley family funnymen.

Jay attempts to make all of Ashton Kutcher’s car dreams come true. Then, Marie Osmond tries to make off with one of Jay's 2021 Ford Mustang Mach 1. Next, Jay gets a little taste of terror from James. Brolin.

Action star Frank Grillo shows Jay the tricks of the action trade in the military-grade infantry support vehicle; Jay tries to give self-proclaimed servant of self-harm, Steve-O, a few more souvenir scars during a thrilling tsunami survival test.

Jay rides a mechanical bull with country icon Dwight Yoakam before they cut loose in a couple of killer Corvettes; Jay views a replica of 007's original Aston Martin DB5; Jay and Paul Reiser ride a pair of Johnny Carson's Corvette-powered swan boats.