When the country star Toby Keith flew to Riyadh in May to play one of the first public concerts held in Saudi Arabia since the early 1990s, he was given strict instructions: no songs about drinking, marijuana, or sex. Complying was no simple task for the author of such sloshed-and-horny classics as “I Love This Bar” and “As Good as I Once Was,” the latter a song in which Keith is propositioned by twin sisters. “It kind of knocked me down,” he recalled when I met him a few months later in Bethlehem, Pennsylvania. “There were only four or five things that I could play that were famous.”

Keith soldiered on with his less racy hits, filling out the set list with rock and soul standards. Until this year, even so tasteful a show would likely have been forbidden in the notoriously conservative kingdom. But, looking to diversify its economy as oil revenues decline, the country recently relaxed its decades-long de facto ban on live music. At the invitation of the royal court, Keith was the first Westerner to be booked. Billed as a night of “Arabian Lute & American Guitar,” the event paired Keith with the oud-playing Saudi superstar Rabeh Saqer. In videos, you can see the all-male audience in white robes and checkered red-and-white head coverings waving their phones like Bic lighters to Keith’s heartbreak ballad “Does That Blue Moon Ever Shine on You.” “They were friendly,” Keith said of the Saudis. “They clapped and boogied and stomped their feet.”

While Keith was engaged in this act of cultural exchange, Donald Trump was a few miles away with King Salman bin Abdulaziz Al Saud, shuttling between stops on his first official trip abroad. According to press reports, their golf cart briefly slowed so the heads of state could take in the concert on a jumbo TV screen. Keith said he hadn’t known that his visit would coincide with Trump’s, and stressed that their paths never crossed, neither during the president’s speech in favor of a more moderate Islam nor during his communion with a large, glowing orb.

Back home, Keith’s concert was nevertheless rolled into the debate over the propriety of Trump’s trip. What were such strident defenders of America, Trump and Keith both, doing fraternizing with a regime that has been accused of supporting the 9/11 attackers? It’s certainly not obvious why a supposed advocate of liberty, justice, and the inalienable right to sleep with twins would perform at a concert one gender had been forbidden to attend. “My job was to represent the West and to reach out,” Keith told me, noting that the concert’s very existence represented an easing of religious extremism. “Who am I to tell them how to run their country?”

The flap was merely the latest in Keith’s long career as one of the most prominent, if professedly reluctant, political figures in contemporary music. Arguably no major entertainer is more associated with the Trump administration than he is, having headlined the president’s inauguration-eve “Make America Great Again” concert, an event that other stars, even conservative ones, sat out. But Keith is registered as an independent, and explains his stance on ceremonial shows with the straightforward logic of duty: If “the president of the frickin’ United States asks you to do something and you can go, you should go instead of being a jack-off.”

In the past, this was not such a controversial position for a country singer to hold. But in an era of unsurpassed polarization, Keith’s willingness to play any gig he can justify as patriotic is newly fraught: Whether he intended to or not, he’s chosen a side. Or perhaps his songbook chose it for him. Keith’s lyrics have long trucked in a mix of nostalgia, irreverence, bellicosity, tribalism, and America-first priorities that we now recognize as a hallmark of Trumpism. Yet, either in earnest or because he’s wary of his fan base shrinking to the size of the president’s, Keith insists that his politics are more complicated than his red, white, and blotto image might suggest.

The 56-year-old Keith has enjoyed one of the most astonishingly successful careers not only in country but in all of contemporary popular music. A former oil-derrick worker and semi-pro football player from Moore, Oklahoma, Keith broke out with the 1993 hit “Should’ve Been a Cowboy,” an elegy for macho independence that became the most-played country song of the ’90s. He followed that up with 20 No. 1 hits on the country charts. Over the course of 18 studio albums, he has demonstrated a knack for both crying-into-your-whiskey ballads (1994’s dejected “Who’s That Man”) and spilling-your-whiskey-everywhere novelty songs (the 2011 viral masterpiece “Red Solo Cup”). He also boasts a business portfolio that spans record labels and a restaurant chain (at Toby Keith’s I Love This Bar & Grill, active military members eat for free). Though his last bona fide hit came in 2012—he blames the dry spell in part on the new vogue for rap-influenced “hick-hop”—he continues to sell out concerts.

Outside of the country world, Keith is better known for his politics than his songwriting. That’s largely thanks to his 2002 anthem “Courtesy of the Red, White and Blue (The Angry American),” in which the son of an Army veteran growls to the perpetrators of the 9/11 attacks, “We’ll put a boot in your ass / It’s the American way.” The biggest hit of Keith’s career up to that point, it became a rallying cry for American soldiers abroad, for whom Keith regularly performs through the USO. It was also the most prominent in a bumper crop of post-9/11 country songs cheering righteous, retributive war. (Fox News recently paired the song with footage of the “mother of all bombs” falling on Afghanistan.) But Keith has long maintained that the perception of him as a “right-wing idiot,” fueled by liberal detractors like the Dixie Chicks and Michael Moore, is simply wrong. He was a registered Democrat until 2008, and he didn’t support the invasion of Iraq. “I’ve had 200 interviews where they go, ‘So, being a Republican, are you … ?’ ” he said. “I just start laughing. I can’t support the troops and not be a Republican. That’s impossible, right?”

Keith says the backlash to his pro-military anthems pushed him away from the Democrats, as did a general shift on the left: “They PC everything,” he said. Still, he made positive, if measured, statements about Barack Obama before his election and traveled to Oslo to play at a celebration of the president’s Nobel Peace Prize win. (Onstage at the Trump concert, he thanked Obama for his service.) Keith told me that he’s tolerant of gay marriage and abortion, and if you listen through his catalog, you’ll hear nods to a certain chicken-fried multiculturalism. “We’re all mud-flap suburbans, all ball caps and turbans,” he sings on 2014’s “Drunk Americans.”

You’ll also hear odes to vigilante justice, gender essentialism, and dads who buy American. Country music has long championed red-state ideals, but Keith has demonstrated a special taste for controversial fare. Few of his contemporaries would have recorded 2011’s “American Ride,” a wry, “We Didn’t Start the Fire”–esque litany of such talk-radio bugaboos as the War on Christmas and the “tidal wave coming ’cross the Mexican border.” And few of his contemporaries are saying anything about Trump, much less playing gigs for him. The rowdy cycles of exclusionary policies and identity-conscious protests of the Trump presidency have made clearer than ever that country music’s frequent celebration of a supposed “real America”—racially specific and traditionalist about gender—isn’t in fact politically neutral, an uncomfortable truth that Keith’s peers still seem to be processing.

Even Keith is cagey when it comes to Trump. During the 2016 election, he disparaged both the Democratic and GOP nominees, and he hasn’t publicly said whom he voted for. He told me that he made his decision at the last minute, adding, “The only thing I didn’t want is another eight years of the Clintons.” So far, he’s cautiously optimistic in his assessment of Trump’s performance, praising his employ of military generals as advisers, shrugging at his fractious style, and offering a standard-issue condemnation of partisan rancor. “There’s a civil war going on,” he said. “All the presidents in the last 20 years, 30 years—the word impeach has come out on every one of them.”

There would seem to be a natural affinity between Keith and Trump. Both are former Democrats who recently became loudmouth, conservative-friendly icons, and both also have a serious knack for branding. I met Keith in August, a few days after Trump’s most vivid threat against North Korea, and when I botched the specifics of the war of words, Keith corrected me. They’ll “be met with fire and fury,” he said, chewing on the president’s coinage as if he was considering a new album title in the vein of 2003’s Shock’n Y’all.

Keith’s latest album, The Bus Songs, compiles new and old material born of men hanging out on a bus and making impolitic chitchat. Keith said songs such as “The Size I Wear” and “Runnin’ Block”—both of which specify the female body types that the burly singer finds attractive or, alternately, repulsive—were designed to entertain in the testosterone-soaked “locker room” environment of U.S. military camps abroad. “We’ve probably got 30 bus songs, but 20 of them we can’t play for anyone else,” he told me, sitting on his tour bus with his buddies. “They’re bad in every way that you can possibly imagine.”

It’s not lost on Keith that this kind of material has become politically charged. “Guys talk like that everywhere,” he replied when I asked about Donald Trump’s “grab ’em by the pussy” comment, also made on a bus and brushed off as “locker-room talk.” “Bill Clinton, everyone was on him about getting a BJ. I was like, ‘It doesn’t affect the way he’s running the country.’ ” He raised the Toby Keith–branded red-plastic cup from which he’d been sipping Jack Daniel’s and addressed the rest of the bus. “I wonder how many presidents did get a BJ in the White House?” he asked, his Oklahoman drawl giving the J a particularly round, plummy resonance.

“At least four,” shot back Keith’s collaborator Scotty Emerick, wearing a cowboy hat and noodling on an acoustic guitar.

“I think Nixon and Pat said they had to watch Deep Throat five times before he could get it down pat,” offered Keith’s manager T. K. Kimbrell to a round of guffaws.

Keith’s national tour has suffered some mild blowback for his playing Trump’s inauguration, with one protest against his booking at an Illinois barbecue festival making the pages of the Chicago Tribune. But Keith says the bulk of his fans—he calls them “redneck, hard-core, old-school, traditional country” people—haven’t changed their attitude about him in the Trump era. “You’re going to get some flak,” he said. “But [to] the people who’re flakking, the other people are going, ‘You didn’t buy an album anyways, bitch!’ ”

There was no sign of controversy in Bethlehem, where I watched him take the stage in the shadow of a decommissioned steel mill. The sold-out audience, more diverse in age than race, toted giant beer mugs—a far cry from the Riyadh show. Keith strode on stage in all denim and a straw cowboy hat, with a cross dangling from his neck. The energetic set spanned his peripatetic career, encompassing ’90s tales of heartbreak, Bush-era salutes to the troops, and his new Bus Songs paean to marijuana, “Wacky Tobaccy”: “If you can’t take the heat, son, vaporize ’er!” At one point, his band members ritualistically passed around a bottle of Wild Shot Mezcal, the liquor line Keith launched in 2011.

When the lights came up after 18 songs, the crowd burst into a spontaneous chanting of “U-S-A! U-S-A!” Keith returned with his band for an encore: “American Soldier” and “Courtesy of the Red, White and Blue.” For the latter song, he pointed at members of the audience holding pro-military signs, and one by one they were brought onto the stage. “Never apologize for being patriotic,” he said. “Fuck ’em.”