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Come a Little Closer: Ten Hours With Dierks Bentley on Tour

Dierks Bentley performs at Jones Beach Theater on June 23, 2017 in Wantagh, N.Y.
Zach Belcher

Dierks Bentley performs at Jones Beach Theater on June 23, 2017 in Wantagh, N.Y.

When you're an artist whose been touring for 12 years, one would think that constantly being on the road gets old and shows begin to feel the same every night. But Dierks Bentley would argue otherwise. 

The 41-year-old singer is currently on his What the Hell Tour, marking the 11th headlining trek of his career. Just as the winter part of the tour kicked off, Bentley decided to extend it through the summer in order to reach more cities and new venues, particularly outdoor ones he couldn't hit months ago. And thanks to the long trek, Bentley is currently the leader of Billboard's Hot Tours tally, playing to more than 500,000 fans and earning $13 million in ticket sales. The biggest reason for adding more dates, though? He's having the time of his life. 

“I think our shows are the best they’ve ever been,” Bentley tells Billboard. “I’m more present now than I’ve ever been. I think this gratitude for getting here -- it’s been a long road to get here -- I’m able to look back at it now and be like, I’ve got all these semi trucks, all these fans, playing venues we’ve never had the chance to play before and we’re selling them out. It’s not about numbers, it’s about being in awe and feeling the joy and wonder of doing this probably more than ever."

Of course, when you're a star of his caliber -- 15 No. 1 hits on the Country Airplay chart, more than 4 million albums sold -- you could get away with simply showing up for your set time, delivering a powerhouse performance, and moving along to the next city. But even with a wife and three kids at home, Bentley's main priority when he shows up to a venue is making sure the fans have an experience they'll never forget, whether it's offering a pre-show tailgate with an acoustic performance or running into the crowd to engage with them more. 

During Bentley’s June 23 stop at Northwell Health at Jones Beach Amphitheater on Long Island, Billboard had the opportunity to hang with the country superstar, getting a behind-the-scenes look into the live he lives on the road. Below, check out a play-by-play of Bentley’s night in New York, including exclusive pictures and some insight into Bentley’s lifestyle from the man himself.

1:30 p.m. EST: Lands at Atlantic Aviation at Farmingdale Airport en route to the amphitheater

A licensed pilot, Bentley and his copilot Austin fly the band out to as many shows as possible — which is as convenient for him as it is fun. "I love flying, so it’s a chance to do a hobby, see my family more, and cut some of the corners off the travel. I never have slept well on the bus, and with three kids, without the aviation, I couldn’t really be doing it at this level anymore,” he suggests. "So it’s really just amazing for us to be able to play all these big venues and be on this climb, but then to be home a lot more — a lot of happy wives and kids.

5:08 p.m.: Takes Ice bath…in a trash can

After participating in Polar Plunge events for the past 14 years, Bentley recently incorporated a daily plunge into his pre-show routine — in a trash can for portable purposes — about six months ago, using breathing exercises by Dutch daredevil/meditation and breathing expert Wim Hof.

"Everything I do revolves around energy management," Bentley explains. "Out here on the road, you’re trying to find like a 5-Hour Energy supplement without actually drinking that crap — when I get out of the cold water, for the next five hours I feel really super-charged, so I don’t have to have as much of the other stuff to take the energy on stage." He adds with a laugh, "You can find energy in all sorts of different forms – certainly tonight will be in the form of Red Bull and vodka."

Jokes aside, whatever form of energy he uses, the most important thing to Bentley is that no city gets less of a show then the next. "You want to walk out on stage and give them all you have -- and I always do. It’s like an airplane in some ways: You can’t have a bad flight, you have to have a good flight. I feel the same way about the show, it has to be awesome every night. There’s so much on the line – these people have come out there, they’ve spent their money and their time to be here supporting us, they believe in us. So I’m always looking for ways to make sure I have full power when I go into takeoff mode for the show.”

6:18 p.m.: Performs acoustic at Tailgate Party

Following his ice bath, Bentley uses a traveling sauna to warm himself up and use the calm before the storm to really hone in on his energy management. But soon enough, he’s on his way to one of his VIP experiences, the Tailgate Party acoustic set, where he plays for a crowd of maybe 100 people under a tent — and he’s technically two minutes early. 

"It’s for those hardcore fans that want a little more,” Bentley says of the mini show. "They get in early, there’s food back here, there’s drinks. We take requests, play songs... we warm up before the show anyway backstage, so it’s kind of like us warming up in front of people.”

After Bentley and his band get their acoustic setup ready, he tells the crowd, "This is always my favorite part of the day, but also like, my most nervous part of the day. Because you just looked at me like you recognize me -- do I look weird? Is my fly down? I haven’t had a drink yet. It’s a little early for me, I don’t go on stage until 9:30, so for you guys, I’m going to hold off a little bit so I have plenty to deliver later tonight."

That doesn't mean he plans to let the crowd drink alone tonight, though. "I’m just trying to meet the crowd at least halfway. If you go into a bar and the bartender won’t take a shot with you, it’s not fun,” he says. "For me, I feel like they’re out there tailgating and having so much fun, they’re pretty lit. I’m not gonna get that lit, but I’ll have some drinks with the crowd, and it kind of helps me connect with them in some way."

6:45 p.m.: Bluegrass band The New York Yankers performs before the show's 7 p.m. start

One of the most recently implemented parts of Bentley’s show nights is a 10-minute pre-show performance by a bluegrass band, which actually changes its name at every gig to be a play on the current city’s name: the Mansfield Manscapers, Scranton Scrotum Boys, Big Jersey Johnsons. The secret to these performances? It’s just Bentley and his band goofing off.

As tour veterans and bluegrass lovers, Bentley and his band incorporated the quick set as a fun way to soundcheck while also giving those early arrivers some music to enjoy before the show actually starts — without even realizing they’re seeing Bentley before his headlining set.

"It’s fun to watch people catch on -- some people don’t,” Bentley says. "And some people are adamant -- a girl will tap her boyfriend like, 'That’s him!' and the boyfriend will go, 'No, that’s definitely not him.’”

7:13-8:05 p.m.: Snaps pictures and talks to fans at various meet-and-greets

After delivering two short performances, it’s time for openers Jon Pardi and Cole Swindell to take the stage, and for Bentley to get camera-ready. He has three meet-and-greets to do in under an hour: Meeting with folks affiliated with Twisted Tea (a tour sponsor), fans who won backstage passes through radio and fan club contests, and employees of local radio stations. But as tiring as that sounds, Bentley says he's always appreciative of the time he gets to spend with fans and the stories he gets to hear. "You get some really meaningful stuff that people have put a lot of thought into,” he explains.

After all of that activity, he finally has time to realize he has yet to eat anything — but rather than eating the catering, he requests a peanut butter and jelly sandwich, “heavy on the PB.”

9:08 p.m.: Gives pre-show pep talk in team huddle before hitting the stage

“Let’s go out there and be present,” Bentley tells the band as they form an arm-in-arm circle. He references the sacrifices that were made for everyone to be there and putting the show on, but recognizes the good time that’s ahead of them: “First time at Jones Beach, it’s gonna be a fun night.” 

9:14 p.m.: Takes the stage for headlining set

“The first times are always the craziest, c’mon!” Bentley exclaims as he begins to play the tour title-inspiring track (and new single) “What the Hell Did I Say.” “I’ve been wanting to play here my whole career. I’ve played Madison Square Garden, but I’ve never played Jones Beach. Thank you for making a dream come true tonight.”

Ten minutes later, Bentley is already engaging with his crowd and getting his drink on, inviting a fan named RJ up to shotgun a beer. “This is my Friday night too!” he jokes.

10:09 p.m.: Makes his way to the B-stage to perform “Riser” and “Home"

After jamming his way through hits like “Free and Easy (Down the Road I Go),” "Every Mile a Memory” and “I Hold On,” Bentley then makes his way through the crowd, high-fiving and smiling his way to a B-stage in the middle of the crowd. Touching on the in-the-audience moment prior to the show, he says, "You’re high-fiving people, you’re holding babies, you’re dancing with the security lady – those moments and physical interactions like that are big highlights for me."

Despite having to trudge through some of the standing water the waterfront venue experienced, he shakes it off [saying “it feels pretty good” and tells a story about the last time he played a show in Long Island -- a wedding that he sang bluegrass music at in the beginning of his career, which he didn’t even have a van to get to. “We’ve come a long way since the rental-car days.”

10:24 p.m.: Finishes the show on the main stage

Upon returning to the stage, he brings out Swindell for their duet “Flatliner,” which brings the energy back up to 100 after the acoustic B-stage songs — so much so that he’s inspired to stage dive on the next song. "I do that every night, but it’s not something I always feel comfortable doing, you know?” he said before the show. "But because that’s there, and you force yourself to do something you’re uncomfortable doing, it creates such a rush when it happens and you get past it, and it’s like, ‘Wow!’”

That rush gives Bentley just the spunk he needs to finish off the show with “What Was I Thinkin',” “Sideways” and encore “Drunk on a Plane,” which featured both Swindell and Pardi singing and dancing along, after coming out in a massive plane prop. The crowd was as electric on the roaring final number as they were when Bentley first took the stage, indicative of the energy he brought the entire night — just as he had told Billboard he wanted from the very start of our venture with him.

“There hasn’t been one show where I felt like I didn’t leave everything I have on that stage and found a way to connect with the audience,” Bentley says. “If [fans] were to walk away [feeling something], the one thing I want them to feel is that they’ve been through some sort of transformative experience, not only with us but with people they don’t even know. I want them to be walking through the parking lot like, ‘Did y’all see that? Was that so fun?’ High-fiving strangers and feeling like, ‘Wow, that was awesome.’"

"I think the one way you can get there is a really genuine experience. So I have to feel that same way on stage and walk off stage feeling that same way if I want them to feel that way. And I do, every time I walk off stage, I’m through the roof," he continues. "You find out next year when they come back whether they felt the way you did or not -- but I think they will. This has been a really fun tour."

Above all, what he hopes his shows make clear is exactly what he proved on that night in Jones Beach: "I love being able to do this for a living, being able to travel and play. I pour everything into it."

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