The Chicagoan’s guide to picking your favorite NASCAR driver

michael jordan

The inaugural Chicago Street Race is fast approaching. On July 2, the NASCAR Cup Series hits the city’s iconic Grant Park to race on a never-before-seen 2.2-mile street course track that uses scenic local landmarks like Michigan Avenue, Lakeshore Drive, and Buckingham Fountain. It’s the first time NASCAR has ever raced on a street course and that it’s happening in the Windy City is no accident. Chicago is a no-nonsense, hard-working town with diverse neighborhoods, great food, and an iconic skyline perfectly suited as the backdrop for a historic road course. It’ll be a barnburner of a weekend. (Not to mention the festival-like atmosphere.)

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Because this is the city’s proper introduction to NASCAR (Chicagoland Speedway, which last hosted a race in 2019, is located in suburban Joliet 35 miles southwest of the city), Chicagoans might need a crash course on the 2023 field. There are so many fascinating drivers each with their own unique personalities, driving styles, and skillsets. To make it easy, we’ve decided to pair some of the most prominent drivers with a beloved Chicago celebrity. This isn’t an exact science (no one here is arguing that the sport’s five-time most popular driver Chase Elliott is literally Oprah Winfrey) but it’s a good rubric to familiarize yourself with the Cup Series.

Christopher Bell – Justin Fields

Justin Fields is the supremely talented quarterback for the Chicago Bears who is entering his third season in the NFL. Christopher Bell is the supremely talented driver for Joe Gibbs Racing in his fourth full-time season in the Cup Series and his third for the iconic Toyota team. Both of these athletes have enough promise, charm, and a tangible work ethic to win a championship.

Ryan Blaney – Dansby Swanson

dansby swanson
Daniel Shirey | Getty Images

Dansby Swanson is swiftly becoming one of the most likable athletes in Chicago during his first year as shortstop for the Chicago Cubs after leaving the Atlanta Braves. Though Chase Elliott has won the Most Popular Driver Award every year since 2018, it’s not a stretch to imagine Ryan Blaney having a shot at the prize this year. Like Swanson, Blaney has had success in Atlanta. They also both look like they could be cousins.

Alex Bowman – Billy Corgan

This pick is a curveball because Alex Bowman looks nothing like the Smashing Pumpkins frontman Billy Corgan and I doubt the No. 48 driver could write something as good as Mellon Collie and the Infinite Sadness (nor would I trust Corgan to be as adept behind the wheel as the seven-time Cup winner). However, Corgan loves animals and has been on the cover of the local animal shelter PAWS’ magazine with his cats. Bowman’s a dog person and has donated thousands to the Best Friends Animal Society to help end animal homelessness.

William Byron – Chance the Rapper

No one wants to see William Byron rap (or do we?) but both Chance the Rapper and Willy B – the latter of whom already has a career-high three wins in 2023 – have carved out great careers so far and have yet to hit their peak. The two are also known to love baseball caps despite the fact that Byron’s been donning ones that are just a tad oversized.

Kyle Busch – Jim Belushi

Kyle Busch is one of the all-time best drivers in the sport who had to drive in the shadow of his older brother Kurt Busch to start his career. Comedian and actor Jim Belushi knows what that feels like as his older brother John Belushi was a Saturday Night Live legend and the star of The Blues Brothers and Animal House, but Jim has had a successful career of his own. And we hear Kyle’s done pretty well for himself, too.

jim belushi
Frederick M. Brown | Getty Images

Ross Chastain – Tim Anderson

Ross Chastain is a Cup Series championship contender but he got there by stepping on a lot of toes and causing some controversy. Like Chastain, the greatest Chicago athletes like White Sox shortstop Tim Anderson (along with Bulls legends Dennis Rodman and Joakim Noah) are the kind of guys you’d want on your team – but absolutely hate to play (or race) against.

Chase Elliott – Oprah Winfrey

Few people have been able to accumulate as much goodwill in Chicago as Oprah Winfrey, whose long-running talk show was filmed in the city from 1986 to 2011. She also famously gave everyone a car one time in 2004. Chase Elliott is the closest NASCAR analog. Like his dad Bill Elliott, Chase has been cleaning up the NASCAR Most Popular Driver Award. The 2020 Cup Series champion has won it every year since 2018.

Denny Hamlin – DeMar DeRozan

Though he’s been driving the 11 car for Joe Gibbs Racing since 2005, Denny Hamlin has never won a Cup Series championship. He’s been close a few times but boasts a Hall of Fame career despite not yet claiming the top prize. NBA veteran DeMar DeRozan is in the same boat. The current Bulls forward and perennial MVP contender almost won in Toronto before he was traded to the San Antonio Spurs. Now, he looks to cement his legacy in Chicago – a town Hamlin’s business partner (and member of this list!) once had in the palm of his hands.

Ty Gibbs – Connor Bedard

On June 28, the Chicago Blackhawks are taking the first pick in the 2023 NHL Draft and most every expert expects the team to pick Connor Bedard, the unanimous choice for that top spot. He’s a once-in-a-generation talent who is expected to rejuvenate the struggling franchise. Ty Gibbs, who drives for his grandfather at Joe Gibbs Racing, is an exceptionally promising rookie in the field, too, though JGR itself is still among the elite.

Kevin Harvick – Harrison Ford

At 47 years old, Kevin Harvick is the oldest active driver in the NASCAR Cup Series field. He boasts an iconic career and while this season is his last, he will forever be a legend. Chicago native Harrison Ford has also announced that his upcoming role as Indiana Jones will be his last. At 80 years old, this isn’t a surprise but we’re grateful for all the memories.

Brad Keselowski – Vince Vaughan

vince vaughn brad keselowski and steve byrne
Chris Trotman | NASCAR via Getty Images

Midwesterners Brad Keselowski and Vince Vaughan have experienced immense success in their respective fields for the better part of the last 20 years. While we haven’t seen Keselowski be a Wedding Crasher, he has stacked up a few wins we love revisiting, just like a Vaughan rom-com.

Kyle Larson – Candace Parker

Candace Parker is one of the best WNBA players of all time. She’s a two-time champion and usually the best player on any team she’s ever been on. Kyle Larson, who won the Cup Series championship in 2021, could easily match Parker’s decorated career the longer he races. He’s already one of the best dirt track racers ever though.

Joey Logano – Bill Murray

The ever-smiley Joey Logano shows up in unexpected places often during the races, namely coming across the finish line at the last possible second out of nowhere. Comedian and local legend Bill Murray lives the same way. You’ll see him randomly appearing at house parties, local bars, and weddings being, you know, Bill Murray, which always makes for a great story.

Tyler Reddick and Bubba Wallace – Michael Jordan

This feels like a cop-out, sure. Michael Jordan is the greatest basketball player of all time but I’m not trying to start any arguments about that by bringing up Jimmie Johnson, Richard Petty, Dale Earnhardt, or Jeff Gordon in this blurb. That’s a different debate. Instead, here’s Bubba Wallace and Tyler Reddick, the current roster of 23XI Racing that’s co-owned by the Bulls legend and driver Denny Hamlin slotting in as the pick(s) here.

Martin Truex Jr. – Jeff Tweedy

I don’t know what Martin Truex Jr.’s music taste is like but I can’t imagine he’d hate the universally appealing Wilco. Like the frontman of the Chicago indie rock mainstays, Truex has quietly built one of the strongest careers in the field over the last twenty years. Both look good in a hat and a beard, too, which doesn’t hurt the comp.