"I have to do this to get boosted up; start my climb," Dierks Bentley, sipping on a spiked energy drink, told Rolling Stone Country a few hours before taking the stage at Bonnaroo on Sunday.
Bentley, one of the few mainstream contemporary country singers to ever appear at the Nashville-neighboring, Manchester, Tennessee multi-genre festival — having made his debut there in 2007 — returned to the farm this weekend. As part of actor/comedian/musician Ed Helms' Bluegrass Situation Superjam, Bentley performed a pair of songs he has sung a thousand times at Nashville's hole-in-the-wall bluegrass haunt the Station Inn and countless Music City pickin' parties over the years. Helms' Superjam was one of three such on-stage mash-ups at the festival this weekend. Other installments saw the likes of the Doors' Robby Krieger jamming with Skrillex and Chaka Khan playing with Derek Trucks.
"It's gonna be totally off the cuff. … People are going to get a chance to see what happens when you go to Ronnie McCoury's house,” Bentley said before the warts-and-all show that featured appearances from Helms' own the Lonesome Trio, Sarah Jarosz, Lake Street Drive, the Black Lillies, the Lone Bellow, Robert Ellis, Yonder Mountain String Band banjoist Dave Johnston and others. Surprise guests the Avett Brothers had to be hastily shuttled to the Bonnaroo's "That Tent" — where they led the band and audience through sing-alongs of the North Carolina Ridgerunners' "Be Kind to a Man When He's Down" and a spirited all-star-jam take on Bill Medley and Jennifer Warnes' Dirty Dancing theme "(I've Had) The Time of My Life" — from the main stage, where they'd just played direct support to festival headliner Elton John.
Helms invited Bentley to join the Superjam when the singer texted the actor/comedian asking if he'd appear in his "Drunk on a Plane" video. "I texted him asking if he'd do it, knowing full well that he's just too big of a star to be in a music video," Bentley recalls. "He should have done it, the video's at Number Two."
But Helms did text back with an offer to play Bonnaroo. "Hell yeah! Are you kidding me?" Bentley responded. "I’m always down for a bluegrass pickin', especially in front of an awesome crowd like this at Bonnaroo.
"I feel honored to be here representing a little of my neck of the woods — country music," Bentley said, "and I'm really excited to be part of this bluegrass [jam] because I love bluegrass music." In 2010, Bentley released the bluegrass album Up on the Ridge, which saw the singer and a star-studded cast of collaborators adapt the style to songs by Bob Dylan, Kris Kristofferson and U2, along with banjo- and mandolin-tinged originals.
After Helms' dry wittingly introducing him as, "a man who traveled very far to be here," during a flood-lights-cueing introduction, Bentley — clad in a baseball cap and long-sleeved baseball tee — strolled onstage and counted Helms and his supergroup into a festive version of Bill Monroe's "Nine Pound Hammer," a song referenced in one of Bentley's own hits, "What Was I Thinkin'." That led into Bentley and company doing his bluegrass gem "Rovin' Gambler," an Up on the Ridge tune he originally cut with the Punch Brothers. The Superjam version boasted some mean flat pickin' from bluegrass luminary Bryan Sutton ("One of the greatest guitarists of all-time," Bentley says), and a wailing harmonica solo from famed rock photographer Danny Clinch.
To a lesser extent, Bentley brought a little of that pickin' party flavor to his 2007 Bonnaroo set, when he tapped bluegrass virtuoso Sam Bush and Americana statesman Buddy Miller to mix things up a bit. "I can't believe it's been seven years," he says, looking back on the gig. "It's crazy how times flies. I'm hoping to come back again and do a full show here."
Along with the likes of Miranda Lambert and Zac Brown Band, Bentley's one of only a handful of country stars to nab a billing at Bonnaroo, which has been going strong since 2002. "It feels like a little bit of a sore thumb; being a country singer at a rock festival," Bentley says, "but challenging yourself always brings out the best. To quote a great movie of all-time, Young Guns: 'When you stop testing yourself, that's when you die.'"