Collector’s Edition

In a town known for its intense love of cars, these meticulous collectors of classic automobiles are the kings of shiny things. We took a peek behind their garage doors.

Ray Skillman

Photography by Tony Valainis/Indianapolis Monthly

For Hoosiers raised on television car commercials, the name Ray Skillman has a nostalgic ring to it. Among the titans of local car dealers, Skillman worships beautiful vehicles, and the 65,000-square-foot showroom that holds his vintage collection is a cathedral of chrome. Amid the rows of Indy 500 race cars, neatly catalogued Corvettes, muscle cars, and pristine American-made oldies, Skillman has tucked other treasures. Restored neon signs hang from the rafters, and a refurbished carousel is the centerpiece of the room.

FIRST CAR A 1950 Ford Business Coupe that his grandfather gave him FAVORITE CAR Mario Andretti’s 1965 Brawner Hawk IndyCar DAILY DRIVE A 2024 GMC Yukon Denali

Shawn Miller

Photography by Tony Valainis/Indianapolis Monthly

He bought his first ride at the age of 13 with paper route money, a purchase that launched his lifelong appreciation for classic automobiles—especially those made in Indianapolis. “Some of the best cars in the ’20s and ’30s were built here,” says Miller. “We had the big three: Stutz, Marmon, and Duesenberg. And these were expensive cars.” Miller is the founder of Significant Cars, a full-service collector-car dealer and broker. A former headhunter with a background in IT, he hopes to someday open a museum featuring Indianapolis cars.

FIRST CAR A 1935 Standard Avon 16-horsepower Sports Saloon, only three of which were made, and Miller still owns his FAVORITE CAR His red 1935 Auburn Supercharged Cabriolet DAILY DRIVE An Alfa Romeo Stelvio

Mike Simmons

Photography by Tony Valainis/Indianapolis Monthly

The founder of Silo Auto Club and Conservancy once made a deal with his wife: When he buys one car, he has to get rid of one car. “I’ve not done so well on that,” says Simmons, whose collection of automobiles grew so large that he opened this downtown storage facility and social hub catering to fellow car fanatics. That was in 2018. “I thought, worst case scenario, I have a place to put my stuff,” Simmons says. Silo’s current membership is around 125, and it offers a full bar and a space for hosting live music.

FIRST CAR A hand-me-down 1968 Pontiac Grand Prix FAVORITE CAR His dad’s 1963 Corvette DAILY DRIVE An emerald green 1995 Toyota Land Cruiser