By Jimmy Carlton Sportswriter Published Jul 08, 2017 at 4:07 AM Photography: David Bernacchi

It’s probably a fawning exaggeration, and maybe it was just great showmanship, but it’s absolutely possible that an indomitable Dierks Bentley and his pair of grinning, grateful openers had even more fun, and were even more happy to be on Summerfest’s American Family Insurance Amphitheater stage, than the awestruck and utterly enraptured audience that delighted in their high-energy, crowd-pleasing, and thrilled-to-be-there performances Friday night.

It sure seemed like they did.

In his fourth show at Summerfest, Bentley was headlining the Big Gig’s biggest stage for the first time, a fact he reminded his adoring fans of often but of which he also seemed genuinely incredulous and thankful. He certainly made the most of the experience with his exuberant stage presence and charismatic novelty acts that have come to characterize his "What The Hell" world tour.

And on a Friday when the party atmosphere was only briefly dampened by an inclement actual atmosphere that dropped cold rain on the uncovered grass seats, Bentley made sure to give extra attention to both his beer-drinking and wet-and-shivering fans.

Bentley took the stage with a bouncing rendition of 2016’s "What the Hell Did I Say" and the raucous 2012 single "5-1-5-0." Then, he got earnest for a bit, telling the audience that this was "a big night for me and my band" because "we’ve worked our way up" over the years at Summerfest, from the small stages to the main one. And then he got rowdy.

In addition to playing many of his hits and some songs off the 2016 album, "Black," and besides the usual swaggering headliner moves like drinking beers on stage and taking phones from people in the front row for pictures, during his bumping 90-minute set, Bentley  did several unconventional – scripted, yes, but still entertaining – things.

Early on, he said he was in the mood for a beer, and challenged a random dude from the crowd to come up on stage for a shotgun chugging contest, which Bentley won easily.

Later, he brought first opener Jon Pardi on stage for a cover of George Strait’s "Write This Down," then showed a photo montage of Pardi superimposed in front of landmark Milwaukee places, such as the Public Market, Leon’s Custard and Lakefront Brewery. For his lovelorn 2016 single, "Different For Girls," he used an incredibly convincing hologram of duet partner Elle King on stage, even thanking "her" afterward.

Following a big, soulful effort – at one point, his voice even seemed to crack – of "Black," the lead track on the eponymous album, and after revving up the crowd with the popular 2013 single "I Hold On," Bentley asked how the rain-soaked people in the grass seats were doing, because he couldn’t see them. Ostensibly struck with an idea, Bentley left the stage, ventured up the aisle on the amphitheater’s south side, high-fiving fans, hugging security guards and saluting police officers along the way, until he got to a makeshift stage at the sound area in the mezzanine.

Climbing up onto the ledge and facing everyone in the grass seats, he played "Riser" solo and acoustic. After again thanking his fans, introducing his bandmates and proudly praising longtime friend and second opener Cole Swindell, Bentley and his group performed a stirring version of "Home," before he walked back around the other side, playfully twirling an usher and retaking the main stage.

With that, he brought out Swindell so the two could do the latter’s 2017 single "Flatliner," which features Bentley. "I’ve been waiting to play this song at Summerfest all year," said Swindell, who repeatedly talked about how appreciative and amazed he was to be in such a position. His opener set was lively and endearing, as the songwriter-turned-rising-star shared his backstory, sang his hits – including "Chillin’ It," "Ain’t Worth the Whiskey" and "Let Me See Ya Girl" – and thanked everyone from the troops and firefighters to fans and Summerfest for serving, listening to country music and letting him live out his dream.

Bentley’s impossibly vigorous homestretch included "Somewhere on a Beach," the lead single on "Black"; the recklessly up-tempo and still-beloved "What Was I Thinkin’," his first number one hit back in 2003; and, finally, an exhilaratingly enervating performance of the infectious 2009 single "Sideways," which left Bentley, exhausted but gratified, on his knees on the stage.

A spent Bentley didn’t have much time to catch his breath after going off stage, however; while the crowd cheered euphorically, the singer was changing into a costume. When the lights came back on, as the first few boozy, sky-high notes of the expected encore, "Drunk on a Plane," honked out, the cockpit of a giant prop plane emerged from backstage with Bentley wearing a pilot’s uniform.

The audience erupted for the 2014 Platinum hit, and especially for the accompanying stunt, and Bentley quickly invited both Swindell and Pardi out to join him for it. The trio, who clearly seem to enjoy each other’s company, danced, swayed and sang, arms around each other, until Bentley tore off his uniform, revealing a T-shirt the NHL Predators fan had on underneath that said, "The road to Nashville goes through Milwaukee." Cue the applause.

Summerfest always books plenty of country artists – Luke Bryan and Zac Brown Band played the amphitheater last week – but Bentley’s concert brought a particular enthusiasm, gladness and glee you don’t usually get with the big-name touring acts. It was refreshing, and it was fun. Even casual fans could understand how Bentley’s rise from Summerfest grounds stage non-headliner to top billing at the amphitheater mirrored his growth and success at large, and that added a local bond and significance to the show.

Early in Swindell’s set, after dutifully playing "Chillin’ It," the Nashville-relocated 34-year-old who started out selling merchandise for Luke Bryan offered one of many personal anecdotes to his Milwaukee audience about that breakout 2013 hit. "I wouldn’t want to chill anywhere else in the world than with you all tonight," he said. "That’s the song that got it all started when I played the Uline stage here three years ago. This is only my second time at Summerfest, and I never dreamed I’d be up here on this stage."

If he follows his buddy’s track, Swindell will be headlining his own show at the American Family Insurance Amphitheater – the "big stage," as Bentley called it – sooner than later. As long as he can dependably win a shotgun race.

Set list

"What The Hell Did I Say"
"Am I the Only One"
"Free and Easy"
"Say You Do"
"Lot of Leavin' Left to Do"
"Write This Down" (George Strait cover with Jon Pardi)
"Every Mile a Memory"
"Up on the Ridge"
"Different for Girls"
"I Hold On"
"Flatliner" (with Cole Swindell)
"Somewhere on a Beach"
"What Was I Thinkin'"
"Drunk on a Plane" (encore)

Born in Milwaukee but a product of Shorewood High School (go ‘Hounds!) and Northwestern University (go ‘Cats!), Jimmy never knew the schoolboy bliss of cheering for a winning football, basketball or baseball team. So he ditched being a fan in order to cover sports professionally - occasionally objectively, always passionately. He's lived in Chicago, New York and Dallas, but now resides again in his beloved Brew City and is an ardent attacker of the notorious Milwaukee Inferiority Complex.

After interning at print publications like Birds and Blooms (official motto: "America's #1 backyard birding and gardening magazine!"), Sports Illustrated (unofficial motto: "Subscribe and save up to 90% off the cover price!") and The Dallas Morning News (a newspaper!), Jimmy worked for web outlets like, where he was a Packers beat reporter, and FOX Sports Wisconsin, where he managed digital content. He's a proponent and frequent user of em dashes, parenthetical asides, descriptive appositives and, really, anything that makes his sentences longer and more needlessly complex.

Jimmy appreciates references to late '90s Brewers and Bucks players and is the curator of the unofficial John Jaha Hall of Fame. He also enjoys running, biking and soccer, but isn't too annoying about them. He writes about sports - both mainstream and unconventional - and non-sports, including history, music, food, art and even golf (just kidding!), and welcomes reader suggestions for off-the-beaten-path story ideas.