And since there is a high probability of a cell phone-toting, toy dog-carrying starlet stepping out in his way, Kenny equipped the ride with road-race quality six-piston 14-inch Wilwood front brakes within the super-fat, low-profile meats.

“To be honest, I don’t think any vintage car, no matter what you do to it, will handle exactly like a modern car, but I don’t want it to feel like that because then it would lose part of the charm,” he says. “Some of the appeal to me is the difference. We try to update it and make it safer, but I still want it to have some character.”

To be sure that the car had enough power to make the chassis really work, Kenny picked up a late-model Mopar Performance Gen III 392 Hemi. The crate engine comes with all the go-fast goodies like a high-lift hydraulic roller cam, CNC-ported aluminum heads, forged crank and rods, a plug-and-play EFI system that’s set up for big power, and of course the Hemi name that strikes fear into, and respect from, all in its path. With all that power right out of the box, he didn’t see the need to throw a bunch of extras at the engine. “Everything is stock on the motor. I figured with 525 hp and 510 lb-ft of torque right out of the crate, it was pretty good for us. We’ve just been fine-tuning it a little bit and trying to get a little more out of it. The thing is, out here all we have is 91 octane and it was set up for 93 octane, so when we started running it out here we had some pinging. So we’ve just been trying to find the right areas where we need to pull a little bit of timing.”

With that kind of power, it didn’t make sense to hook it up to a lazy man’s slushbox, so Kenny installed a six-speed Viper transmission and a Mopar-supplied Dana 44 with 4.10 gears to send the power to the pavement. A modern take on the infamous Pistol Grip shifter was created by Billet Technology and matched to his reach for comfort and performance.

Subtle styling cues were the theme for modifying the body. “Unless you’re a Mopar guy, a lot of people don’t know what the car is when they see it,” he says. Even those in the know aren’t always hip to the modifications right off the bat. “It takes even a trained eye a few times to look the car over to see what we did,” he says. “We shaved the driprail moldings, keyholes, and side-marker lights, tucked in the front bumper, and with the rear bumper we smoothed and shaved the entire rearend. We molded the entire rear bumper into the body so there’s no seam of any kind. We used ’69 Charger door handles instead of the door handles that came on it.”

Inside, the ride continues bypassing the mainstream. Kenny incorporated Chrysler Sebring convertible seats for the added safety of a built-in shoulder belt without having to install ricer-looking four-point harnesses. Keeping with the updated theme, the car sports a clean modern interior, air conditioning, cupholders, and a kick-ass stereo. “It’s got everything except for safety airbags,” he says. With all the work done to the car plus the original Detroit steel in place, there was a small weight penalty to pay, but it was compensated for. “The car is huge! I think it’s like 18 feet long, and I don’t even know how much it weighs, but that 392 Hemi just gets up and goes,” Kenny says. “I built this car to drive the crap out of.” And that’s exactly what he’s been doing.

As a world-renowned blues/rock guitar hero, Kenny is used to being treated a little different. Likewise, his ’72 Charger also spends its life outside the lines of normalcy. Living outside the boundaries of 9-to-5 society is what puts both of them on the fringe. Perhaps that is why they make such a perfect match for each other as a pair of black sheep.

Kenny Wayne Shepherd’s ’72 Charger ain’t your regular grocery getter—but it does that too.