By the time Billy Joel arrived in the Soviet Union for a string of six concerts, he was visibly worn down from 11 straight months of touring. The 38-year-old singer was wrangling a traveling crew of 130 people, including his wife and their one-and-a-half-year-old daughter, and it was costing him two and a half million dollars of his own money to be there, money he knew he'd never earn back. His throat was sore and he feared his voice would blow at any second. On top of all that, the whole world was watching. Being one of the first major American artists to perform in the USSR since the construction of the Berlin Wall put him under a microscope, and he was expected to be a stellar ambassador for the United States during what looked to be a thaw in the Cold War. But, the fate of international politics aside, he was still a guy from the streets of Long Island —a once amateur boxer, high school dropout, and reputably pugnacious pop star with a short fuse. It had been a long year for Billy Joel and something was bound to give. Then on the night of July 27, 1987, in front of 22,000 people, it did.

But Gorbachev liked rock and roll. His wife was an Elvis fan and they were both great admirers of John Lennon. And while American music became more prevalent on the Soviet radiowaves under glasnost, Gorbachev wanted to import the real thing in the form of concerts. He and President Ronald Reagan signed a United States-Soviet cultural exchange agreement in Geneva in an effort to open new lines of communication. American acts like James Taylor, the Doobie Brothers, and Santana had accepted offers to play shorter festival sets at a concert for peace in Moscow in the summer of '87. Elton John had also done an intimate performance there in 1979. But what the Soviets had never seen before was a full-on stadium rock show, and Billy Joel was ready to give it to them.

Joel's Soviet trip was two years in the making. When Mikhail Gorbachev took over as leader of the Communist Party there in 1985, he steered the Soviet Union onto a drastically new course, promoting policies of glasnost (openness) and perestroika (restructuring) in an effort to end the political and economic rivalry between the Soviets and the US that arose after World War II. Western culture had previously been explicitly banned under the nation's old totalitarian rule, though rock and roll, a distinctly American export, had managed to seep in via the black market. Bootleggers would smuggle records from the West and etch makeshift copies of them on discarded X-Ray emulsion sheets fished out of hospital dumpsters. These were sold in secret on street corners and alleys, and the practice gained popularity during Beatlemania in the 60s. It was entirely possible to illegally purchase a copy of A Hard Day's Night on the streets of Leningrad printed on an X-Ray of some poor bastard's broken hand.

Depending on whom you asked back in the States, Joel was either a pop genius or a glorified lounge singer. Some critics questioned whether he was the most well suited man for the job. The Chicago Tribune would run an article that summer examining that notion under the headline "Was Billy Joel Rock's Best Rep To USSR?" And while the Soviet Ministry of Culture reportedly also extended invitations to other American artists including Bruce Springsteen and Stevie Wonder, Joel had this advantage over all of them: He said yes. International touring with a stadium show is difficult enough pull off, and the added complications of heading to uncharted territory seemed to scare other artists away. But Joel was the first to jump at the opportunity, taking the initiative and booking six shows there for July and August, 1987.

Beyond money, though, there was something greater at stake. Joel, who grew up among the millions of other American children who practiced ducking and covering under their school desks during routine Civil Defense drills, was raised to fear and distrust the mysterious Ruskies. Though he made it a point of downplaying his ambassadorial role when speaking to the press, he privately hoped that his trip would be something of a peacemaking expedition between the two enemy nations. He tried to lower expectations as much as he could, presenting himself as a mere entertainer, mostly to save face in case the whole thing was a disaster.

It was immediately obvious this wouldn't be a financially profitable venture for Joel. "They paid you in rubles, which wouldn't buy anything, and there was nothing to buy when you were there," Joel once said. He put up a reported two and a half million dollars of his own money to cover the production, knowing he was sure to go into the red. In an attempt to recoup some of the cost, he brought along a film crew to shoot a documentary for HBO, Billy Joel From Leningrad, U.S.S.R., and record a live album, Kontsert, for Columbia Records. (Both were later repackaged in 2014 as A Matter of Trust - The Bridge to Russia.)

Joel and Brinkley celebrated with their gracious hosts afterwards. "Boy, they rolled out the red carpet," Brinkley remembers on A Matter of Trust. "So much wine rolling and vodka, dancing, and music, and singing." But the night of partying and impromptu singing had its price. When Joel arrived in Moscow a few days later for his first of three shows at the Olympijskiy Stadium, his vocal cords were shredded and he was having trouble hitting the high notes during his warm-ups. He visited a medical clinic where a doctor gave him an injection, put electrodes on his throat, and, for some reason, handed him a box of Tic-Tacs and told him to pop a few every so often.

Joel first arrived in Tbilisi, the capital of the Soviet Republic of Georgia, where he and his then wife, model Christie Brinkley, spent time sightseeing—taking walks through outdoor food markets and snapping photos with townspeople. After befriending a few local singers, Joel was invited to a nearby opera house that evening for a jam session, but he arrived that night to find that 1,000 tickets had been sold, and it turned into a full-on performance. It wasn't an ideal setup but Joel made due with the subpar house PA, often shouting to help his voice carry to the back of the room to reach the far rows.

But even though he tried to minimize the political aspect of the trip, his entry into the country was such a spectacle that it was a political act itself. He brought his entire production with him to do his show "lock, stock, and barrel, exactly the way we do it in the States," as he put it. That included everything from the lights to the stage to the speakers, all packed into six semi-tractor trailers, plus several buses full of crew. People lined up on the streets to watch this display of American grandiosity as it rolled through their country.

"I'm not a politician," he said in a May 1, 1987, press conference. "I'm going there as a musician. I want to get more communication going between us. People over there like pop music, they like rock and roll."

Even though the bigshots were gone, Joel still worked himself into a sweat trying to make a connection with the remaining crowd, which he felt was key to a successful performance. "A good concert is an exchange of energy—you make a noise, they make a noise," Joel said on the live album's commentary tracks. "It's like sex. If it's too quiet, you're not doing it good." And this show was too quiet for Joel's liking. He prided himself on being a workmanlike performer, and if he had to individually engage with every single person in the crowd of 22,000 to win them over, so be it. Over two and a half hours, Joel did just that.

But when Joel finally got on stage for the first show, he had a bigger problem to deal with than a sore throat. As he pounded away on the keys of his black Yamaha piano, belting out bangers like "My Life" and "Angry Young Man" with the rest of his band, he noticed that the audience was as still as, in his words, an oil painting. Looking out into the crowd, he saw the stoic faces of middle-aged men and women, many of them Communist Party functionaries who received tickets as a perk, looking cock-eyed and confused, occasionally offering polite, tepid applause. Joel attributes this lukewarm response to the "bigshots who got the tickets in the front" being too turned off by the unprecedented display of bright lights and loud volume to emote any enjoyment. "Which I kind of wanted," he says. The way Joel tells it, once the bigshots finally gave up and left, they gave their tickets to the younger, more enthusiastic people in the back rows and those waiting outside, at which point it finally turned into a real rock and roll show.

During "For the Longest Time," he ran down the aisle with a wireless microphone, grabbing people out of their seats and leading them to the front of the room like the pied piper of pop. Before long, he had gathered a congregation around the edge of the stage. And since there was no barrier, they could reach out and touch Joel's legs and feet, bopping along to songs they'd mostly never heard sung in a language they mostly didn't speak. After hits like "Uptown Girl" and "It's Still Rock and Roll to Me," the show ended with a treat for those who had been sneaking Beatles records for the last few decades: A cover of "Back in the U.S.S.R."

By the time the next night's show rolled around, Joel was even more stressed from doing another day of interviews and seeing even more sights with his wife and meeting even more locals and hearing even more crew members backstage ask how his voice felt and telling them that it hurt even more than the night before.

"By the end of the show, the crowd looked like it could have been Detroit, it could have been Philadelphia, it was the same thing," Joel would tell The Today Show via satellite the next morning. The press back home rewarded his efforts. "A Rocking Billy Joel Breaks Through Soviet Reserve" read a headline in The New York Times, whose article began: "Billy Joel brought his rock-and-roll here today and won the souls of those in a stony Soviet audience, leaving them cheering, dancing on chairs and looking around in fearful wonder as they followed the music and not the rules." By all accounts, it was a success. But, of course, that was only night one.

The Soviet crowd, raised by decades of Iron Curtain austerity, stopped dancing and froze like deer in headlights when they were lit up, petrified that the security guards would crack down on them. Then the lights would go out again and they'd resume dancing. Lights off, dancing. Lights on, frozen stiff. This went on and on like a game of red light, green light, one-two-three. With each flick of the lights, the perfectionist Joel saw his hard earned connection fading away. Mid-song, he started screaming at his crew to cut it out and, like a consummate professional, didn't even miss a beat as he barked orders between lyrics.

In an attempt to speed up the connection process with a fresh slab of audience, he cut many of the ballads from the second night's set to lean on the surefire crowd-pleasers. One song that seemed to win over the audience was his 1980 Top 40 hit, "Sometimes a Fantasy." Sure enough, when Joel looked over his piano which was situated towards the rear of the stage, he didn't see a crowd as still as an oil painting for the song. Instead he saw exactly what he hoped for: people throwing their hands up and dancing. They were having so much fun, in fact, that his documentary crew wanted to get better shots of them and shone the house lights on the first few rows. But that caused a huge problem.

"When am I gonna take control, get a hold of my emotions? STOP LIGHTING THE AUDIENCE!

Why does it always seem to hit me in the middle of the ni-i-ight? STOP IT!

You told me there's a number I can always dial for assistance. LET ME DO MY SHOW FOR CHRISSAKE!"

"I hear Billy singing and he's saying something, but I can't hear what he's saying," lighting director Steven Cohen recalled in A Matter of Trust. But even though Cohen couldn't make out Joel's words, he would definitely recognize what came next—the sound of a piano crashing onto the ground. The five-foot-five-inch Joel had gotten a sturdy grip under the keys, put his back into it, and, with red fury in his face, flipped the whole thing over. Band and crew members recall stray chunks of Yamaha whizzing past them as the piano landed completely upside-down with a loud crash.

With the crazed eyes of a man blacked out on rage, Joel hopped past the overturned piano and stormed towards the front of the stage just feet from the crowd. Since those in attendance had never seen a real rock and roll concert before, they clapped and applauded, thinking it was all part of the act. Joel picked up a microphone stand, swung it above his head, and bashed it into the floor like a lumberjack chopping wood and the crowd cheered even louder. Joel's petrified bandmates stayed clear of his warpath but didn't stop playing, and neither did he. He landed a flying kick into his grand piano as he continued to sing, "Sure it would be better if I had you here to hold me." Then he took a hard swing at it with the mic stand and knocked a big dent into it. The bottom half of the mic stand snapped off and he continued singing into a broken stick while the crowd went wild. No wonder rock and roll shows were so popular in America, they thought. For just five rubles, you could watch a curly haired man beat a piano half to death with a microphone stand. What a deal!

Even though Joel cooled off enough to get the concert back on track, and later apologized for his "real prima donna act" in post-show interviews, the headlines back home turned on him the next morning. "Billy Joel Has A Tantrum" read an Associated Press story picked up by The New York Times.

"I've been on the road for 11 months," he told the reporter. "It's difficult. I'm running ragged."