It was 74 years and two weeks ago when NASCAR ran the first race of its Strictly Stock division, what we now know as the Cup Series. In the years since, over 2,696 races, those stock cars have rumbled around ovals of dirt, asphalt and concrete, over road courses, through an Atlantic ocean spray, between sand dunes, and even inside ballparks, football stadiums and across an airport tarmac in New Jersey.

This weekend, though, those machines and the drivers within them will navigate a raceway unlike anywhere or anyone before them. They will steer their way through the Loop Community of Chicago, the first true street course ever run by the world’s preeminent stock car series.

These cars weren’t built for this. Michigan Avenue and Lake Shore Drive weren’t built for them. The racers seem to be worried about the course’s raciness and the cockpit heat produced by the special mufflers that will be affixed to the exhaust systems that will be on their cars for this race. Why? Because of the complaints from a not small number of Chicagoans who like to spend their Independence Day weekend hanging out Grant Park, a little irritated about 800-horsepower machines running red lights and shaking walls all weekend, especially the walls of museums covered in fine art.

So, a question: Why even do this?

OK, an answer. And it comes from a man who knows a little something about turning left and right in a high-end racing machine on the same streets where regular folks do the same in city buses and minivans.

“Why not?” says Jenson Button, the former F1 superstar who made 16 starts in the Monaco Grand Prix, including a win during his 2009 world championship season. He’ll be making his second Cup Series appearance this weekend after finishing 37th in his debut in Austin on March 26. “I think it’s great that they’re willing to attract something different, and if it doesn’t work, it doesn’t work. It’s one race on the calendar.”

It might not work. But do you know what? It might work beautifully. Like, literally beautiful. Brightly colored NASCAR Next Gen machines banging doors and hammering down Columbus Drive with the Chicago skyline in the background? That doesn’t sound so bad, does it?

“At the very least, it’s going to look cool, right?” said Ross Chastain, who won for just the first time in 2023 last weekend at Nashville Superspeedway. “I think that willingness to try something different, that probably wasn’t easy for NASCAR, but they’ve certainly been doing it a lot lately and for the most part, yeah, it’s worked out.”

That willingness is still very new. For seemingly forever, the Cup Series schedule went to the same racetracks on the same weekends to run the same races. That’s not a terrible way to go about your business, establishing routines for fans and teams, but it’s only good when it’s working, and it for a long time it did. Then, it didn’t. The fear for NASCAR brass, who admittedly had thrown too much change at their fanbase during the mid-2000s — see: Car of Tomorrow, leaving traditional markets for new racetracks out West, a constantly changing postseason format, even an internal ban on booking country music acts — was that breaking away from the traditional schedule might feel like a history of too many extreme makeovers repeating itself.

“Mindful change is the goal. New ideas that will get people excited, but ideas with roots that come from what made NASCAR great in the first place,” NASCAR president Steve Phelps explained during a preseason chat in his Daytona office. “We all acknowledge concerns and hesitation.”

When they finally got past those concerns and hesitation, though, wow, did they really get past them. Like Chastain wall-riding the final turn at Martinsville last fall.

The Chicago street course is only the latest rollout amid a five-year stretch of “Let’s give this try” ideas that not so long ago NASCAR never would have even considered.

First came the infield layout at Charlotte Motor Speedway that made “Roval” a real word. That was followed by covering Bristol Motor Speedway in dirt. Then the Brickyard 400 at Indianapolis Motor Speedway was moved from the oval to the road course and from August to July. The season finale shifted to Phoenix after 18 years at Homestead-Miami Speedway. Lights at Martinsville Speedway; adding more road courses; building a temporary oval inside the L.A. Coliseum for the preseason Busch Light Clash; going back to the track where Chastain just won; looking at another Nashville date at another track, the legendary Fairgrounds; and the pièce de resistance of this racing renaissance, taking the now-mobile NASCAR All-Star Race and dropping it into North Wilkesboro Speedway, a track that had been closed for nearly three decades.

“I think that on paper, it might feel like a lot, and it is a lot,” confessed Marcus Smith in May, the CEO of Speedway Motorsports Inc. (SMI), owners of 11 racetracks that host Cup events, including the nucleus of those changes in Bristol, Charlotte, North Wilkesboro and Nashville. “But you also might hit a home run. And for all of the changes made, if you really look, we’ve all worked very hard to ensure that a familiar foundation is still there.”

He’s not wrong. Although some of their dates have been shuffled and at least one facility, California Speedway, will be offline in 2024, a whopping 21 racetracks that hosted points-paying Cup Series races in 2019 were still on the schedule this year. And although the downtown Chicago street course is new, the market is not. Chicagoland Speedway, located in Joliet, Illinois, hosted 19 Cup Series races from 2001 to 2019.

“I believe what is exciting about what is happening now is the enthusiasm to try stuff,” Smith continued, pointing to the racetrack behind him, resurrected North Wilkesboro. “Swing for the fences. You might swing and miss big. But when you connect, you might connect big, too.”

To that point, some of those grandiose ideas have worked. Some haven’t. A substantial chunk of them were testament to “necessity is the mother of invention” ideas that were born from the chasm of the 2020 pandemic. It was NASCAR that returned to facilities and televisions first among all major American sports. Determined to get in a full 36-race season despite going dark for nearly 10 weeks, Phelps and his team bunkered into a Daytona conference room and threw every idea against the wall. They booked doubleheaders and midweek races. Somehow, it worked.

It also kicked open a door that had already been cracked.

“People forget now, but that 2020 schedule was already full of big changes even before the pandemic,” recalled Ben Kennedy, NASCAR’s senior vice president of racing development and strategy, earlier this spring. “The Brickyard and season finale moves were already on the books for that season. So was the doubleheader at Pocono Raceway and Martinsville under the lights. And our riskiest idea, that started in the fall of 2019.”

He is speaking of the Busch Light Clash at the Coliseum. Kennedy, then the just-promoted VP of racing development, was only 27 years old and less than two years removed from his final Xfinity Series start as a driver. When he met with the operators of the nearly century-old home of the Olympics and the USC Trojans, they thought he was inquiring about hosting a NASCAR cooperate event. Then he told them he wanted to build a racetrack inside their football stadium.

“To me, that’s it. That’s the whole thing. Be bold. Why not?” says Joey Logano, who raced against Kennedy nine times between the Xfinity and Trucks Series. “It’s not trying crazy stuff just for the sake of trying it, but ideas that will feel like NASCAR. If it doesn’t work, OK, don’t do it again. But if it does, then it should be all that you want it to. Create something that old school fans will be interested in, but also grab other people’s attention.”

The inaugural event the L.A. Coliseum did that. It created a preseason buzz among established fans and casual TV viewers suffering from a post-football hangover that was palpable two weeks later during Daytona Speedweeks. It also opened up conversations with other potential nontraditional venues. Like, say, the downtown of America’s third-largest city.

“The Chicago event is here because of what we did in Los Angeles,” Kennedy, now 31, explained in May. “The conversation about that event started almost immediately following the 2022 Busch Light Clash, and now we are here. It’s exciting when ideas come to fruition, for everyone.”

It was Kennedy’s great-grandfather, Bill France, who founded NASCAR 75 years ago and as its first president booked racing events wherever they would have him, from long-ago demolished road courses to horse racing tracks and even Chicago’s Soldier Field, home of the Bears. Kennedy’s grandfather, Bill France Jr., streamlined that schedule during the 1970s and created the baseline calendar that the Cup Series largely stuck to for its greatest decades of growth. It was his mother, Lesa France Kennedy, who was the leading pioneer of finding new markets and venues for the sport during the 1990s and 2000s, with some huge hits (see: Kansas Speedway, Chicagoland Speedway) and some huge misses (shuttered exploratory projects in Seattle, Denver and New York).

Now, with that DNA and with the cooperation of the NASCAR Steves (Phelps and COO O’Donnell) as well as Marcus Smith and SMI, Kennedy sits in rooms full of people who are excited to figure out what’s next and to have a discourse on big-swing ideas. Finally. Like Kennedy, though, those people all have their own deep-rooted NASCAR DNA that is always whispering in their ears …

“If it feels like a great idea and you have the means to try it, then try it,” Kennedy says his inner voice tells him. “But what makes it a great idea for us, no matter how out-of-the-box it might be, does it still feel like NASCAR? It needs to. Because if you strike that balance, then it’s hard to lose.”