The purpose of this trip could be summed up neatly: I was driving from New York City to central Connecticut, to a casino called Mohegan Sun, owned by and greatly enriching the descendants of a subjugated Native American tribe, to see a friend of mine sing for a rock'n'roll band called Starship.

I should back up. Starship is a band that emerged from another band, Jefferson Starship, which itself emerged from a previous band, known as Jefferson Airplane. The latter was an iconic band of the 1960s: they played Woodstock, Altamont, Monterey, and were central to San Francisco's Summer of Love. Jefferson Starship was the 70s incarnation of the band, after various original members of the band had departed. Starship was yet one more version, prominent in the 1980s and featuring singers Grace Slick and Mickey Thomas. They scored a colossal hit with the song "We Built This City," and soon after, Slick left the band, and they stopped recording. But periodically after that, Thomas would tour under the Starship name, playing smaller venues and casinos like the one at Mohegan Sun, in the middle of one of the oldest states in the Union.

We should back up more. Colonists from England, seeking religious and economic freedom, began coming to America in the 1600s. They pushed inland from the East Coast and soon were all over Connecticut, crowding the native population, which in that region included the Pequot tribe and the Mohegans.

The colonists brought diseases with them against which the Mohegans had little defence and who, weakened and overmatched, chose to form an alliance with the English, and who soon fought with the English against the Mohegans' traditional enemy, the Pequot. As a result of those battles, and through innumerable dubious land deals and land grabs and the assimilation of the Mohegan tribe into mainstream white culture, by the 1800s the Mohegans had dwindled to about 400 members and controlled only a few thousand acres near the Thames River Valley. And by the 1900s, Mohegans had virtually no tribal land at all. Worse, when the US government began recognising certain tribes in the 1970s, granting them sovereign-nation status and the right to (relative) self-determination, the Mohegans were not among those tribes recognised. In a decision that defines perverse, the government that drove the Mohegans from their land and forced their displacement and loss of culture refused to recognise their existence, asserting that the Mohegans had failed to keep adequate records of their meetings and affairs, specifically citing a lack of documentation of the tribe's activities in the 1940s and 1950s.

But in 1992, the Mohegans' chief Ralph Sturges revived the effort to get federal recognition, and was soon aided by some new and powerful friends. Three companies – RJH Development, LMW Investments of Connecticut and Slavik Suites Inc of Michigan – together proposed the idea of building a casino on ancestral Mohegan land. The Mohegans liked the idea, and the companies, in their great generosity, then provided expensive attorneys well versed in applicable laws. These attorneys aided the Mohegans in getting their tribe recognised and, under the Mohegan Nation Land Claims Settlement Act of 1994, which granted the tribe control over their ancestral land on which they could do what they pleased, the Mohegans decided to build a casino-resort-entertainment complex.

It gets stranger. First, the Mohegans needed to buy back some of the land historically theirs, the only problem being that a nuclear power plant had been operating there. The good news was that the plant was dormant – it had been a military contractor, providing the navy with nuclear reactor fuel components during the cold war, and decreased demand for nuclear subs meant closure of the plant. So the Mohegans, the tribe of subjugated native people, bought 97 hectares (240 acres) from the United Nuclear Corporation, a company that provided to their subjugating government nuclear materiel for potential wars with a foreign enemy. After buying the land, the Mohegans cleaned it up to meet state and federal remediation requirements, and broke ground in 1995. Tribal dancing was done to commemorate the occasion.

The Mohegan Sun hotel and casino. Photograph: Getty Images

In 1996, the casino opened, featuring 2,500 slot machines and 170 gaming tables. The creators of Mohegan Sun were dedicated to attracting families to the complex, so they built a 560 sq m (6,000 sq ft) entertainment centre called KidsQuest, which offered hourly childcare and diversions, including the Kiddie theatre and something called Barbieland, for parents who wanted to drink and gamble with consciences unencumbered. The casino employed almost 5,000 people, many of whom had previously worked at the power plant. All the employees, the vast majority of whom were white people of European descent, wore as their uniforms buckskin outfits to honour the Mohegan forebears who, in the most bizarre of ways, made their jobs possible. The casino was an instant success, with first-year profits reaching $36.9m.

In the middle of the casino was the Wolf Den, a cosy theatre open to the rest of the casino space, where performers could entertain the 350 or so people within the stage area and the thousands more in the casino at large. And it is in this Wolf Den that Starship had been booked to play on this certain weekend in 1999.

The problem, though, was that this particular incarnation of Starship, at this particular moment, had no women among its ranks, and this fact would have violated the contract the band had with the Mohegan Sun. The contract stipulated that they had to have a woman on stage with them, and the problem at this juncture was that Thomas, the band's lead singer, was on the outs with his girlfriend, who happened to be the band's backup singer and sole woman member. All of this, at least, was what Julie had been told.

So the manager of the Wolf Den called the manager of Starship and conveyed to him this: if Starship wanted to be paid, they needed to have a woman on stage, period. The Wolf Den manager did not care what the woman did on stage, if she danced or sang or played the tambourine, but Starship could not be just a bunch of old white guys playing old songs. There needed to be youth represented, and womanhood represented, and it would be even better still if the woman was cute and would move around a bit.

So my friend Julie, who at the time was singing and playing guitar in her own band in San Francisco, one day got a call from the guitarist for this touring version of Starship. He wanted to know if Julie might want to fly out to Connecticut for a two-night gig, singing backup. The flight and accommodation would be free, and she would be paid $200 a night. Julie laughed, and then said yes, and the guitarist sent her a tape of the songs they would be singing, and, soon enough, Julie was flying into the Hartford airport, where she was picked up in a limousine and driven to the casino to meet the band, run through the set list and do a soundcheck. During this soundcheck Julie was told that if she was nervous about all this, and nervous during the show, they could turn her microphone down, or even off – that she really had no obligations outside of standing on stage, ideally with a tambourine. But after the soundcheck, and after hearing her vocals, they decided to turn her microphone up. Julie could sing.

The next day, I rented a car in New York city, where I was living at the time, and began the drive up 1-95 to central Connecticut. It's important to note that I was going to the show thinking it would be very funny. I had no real interest in Starship, and knew only two of their songs, the one called : "We Built This City" and the one called "Sara", a love song also popular in the early days of MTV. Both were what is known as "pop-rock" or "pop" music, and both were lavished with scorn by the ranks of music critics, and others, who deem themselves aesthetic arbiters, tastemakers and judges of what is good music and what is not.

I was one of these people. Or thought I was. Or wanted to be. I took great pride in the fact that I was buying REM's Murmur the year it came out, 1983, when I was 13 and they were unknown. I took great pride that I was buying obscure Pere Ubu imports when I was 14, the age at which I was subscribing, with great difficulty from my Illinois suburb, to the Village Voice. Then, and for many years after, I thought I was some kind of music expert, and wouldn't have minded being called a snob, even though, truth be told, I knew almost nothing about music, beyond these bands of a certain type, and knew nothing about any music whatsoever made before 1978, except for the soundtrack to Pennies from Heaven, starring Steve Martin, a movie and album I had, inexplicably, felt deeply connected to. The point is that I knew nothing then, but felt that music was a wonderful way to divide people, to assess their cultural knowledge and use it to arrange them in complicated taste-based caste systems.

So I was driving up 1-95 feeling very happy that I would be seeing this absurd thing, Starship playing a casino with my friend singing backup. It was the kind of end-of-the-meaningful-world hall-of-mirrors I appreciated at the time, and I thought the whole thing would be a many-layered joke that could not be improved upon, with a joke band playing a joke venue, with my friend in on the joke – standing there, on stage, knowing the joke while participating in the joke, and she and I, and probably the band, too, having a big laugh on the audience, who, we assumed, were silly enough to like this music, silly enough to like going to casinos in the middle of the Connecticut woods, ridiculous enough to go to a place called the Wolf's Den to see a many-times-reconstituted band play old songs, none of it moving the world of Art and Progress and Purpose and Real Meaning forward an inch.

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Pulling into Mohegan Sun, I was startled by the fact that it was not some gaudy complex just off the highway, brightly screaming from 10,000 lightbulbs the size of human heads. No, it was actually something that no one would have expected from a casino: it was subdued. The exterior, the grounds, nestled amid a few hundred acres of dense forest, were positively tasteful. The experience of entering the complex was more like the long drive into a golf course or forest preserve. Disquieted, I checked into the hotel and waited in the lobby for Julie and the band.

Soon, two men emerged, each in their mid-30s. Both were thin, both wore black jeans and both loitered in the lobby as they and I waited for Julie. They'd had a soundcheck earlier in the day, so the two men knew her. When Julie emerged, everyone smiled, I greeted her, was introduced to the two musicians, and we all made for the door. Outside, there was a limousine, and, seeing it, I thought of a joke. I batted it around in my head, deciding if it was good enough to use. I went ahead because I was new and at the very least they'd have to laugh politely.

"Ah, rock star parking," I said. Writing that now is very painful.

They all laughed. Writing that now gives me peace.

Inside the limousine were two others. I can't remember everyone's names now, but I know that in that limousine I met Mickey Thomas. He was dressed casually, like he was heading to get some food at a sports bar – snug, faded black jeans and a loose button-down shirt, perhaps made of silk. I remember it having a sheen.

"So you live around here?" one of the band members asked me.

I said I did not.

"So what brings you to these parts?" the band member asked.

"This, actually," I said.

The band member was momentarily surprised to learn I'd driven for three hours to come to this show at a casino in the woods, but he quickly adjusted to the attitude of the rest of the band – that it made perfect sense to travel that far to see them play. Mickey was looking out of the window, at the bare winter trees, the white patches of snow. It all looked very cold as we passed slowly through a long wooded driveway and into a crowded parking lot. Instead of parking there, amid the frozen unwashed making their way inside, we descended underground, to an entrance for performers only.

Soon we were in the dressing room, where there were fruit plates, sandwiches, a case of Evian, a cooler of beer. A TV hung from the ceiling and one of the band members turned it on, found a hockey game and, 20 minutes before the show was to start, the entire band began watching. Julie and I sat there, not sure what to do.

Eventually, one of the guys said, "Well, we're on in about 10 minutes. You want to get a seat?"

I left the green room and two turns later I was on the stage. I'd either taken a wrong turn or this was the only way out. It was momentarily jarring, some of the audience assuming I'd be giving some announcement about the band's imminent arrival. Instead, I quickly stepped down to the concert floor, which was occupied by a few hundred people sitting at tables. I passed through and out into the casino at large.

I did not know then, and still don't know, much about casinos. I don't know if they're immoral at their core, merciless in their aims to take the money of those with loose grips on their earnings or addictive personalities. I don't know if they're predatory. I don't know much about the morality of Native American tribes gaining some measure of prosperity by opening gambling facilities on their land. The surreality of this turn of events for Native Americans has been noted a thousand times before, and I can't add much to your knowledge of casinos here, their ethics or past or future. But I will say that while walking around that night, a cold beer in my hand, I was astounded.

The Mohegan Sun casino and resort was more beautiful that night than it had a right to be, and was, to my eyes one of the more beautiful interiors I'd ever seen. I know that sounds like the most ludicrous kind of hyperbole, but you should know that I love casinos and have loved them since first seeing Reno in 1993. Reno is in many ways a very desperate town, and it's dark and broken at its corners, but when Reno is good, it's gorgeous. It is manmade, and it's absurd, as if built by children who were never told "No". It glows like all stupid hollow unjustifiable optimism embodied. Reno is beautiful that way, too, but the Mohegan Sun was far more beautiful and in a very different way. Whereas Reno, and much of Las Vegas, is entrancing in its rococo extremities, so tacky that you're drawn to it like you would be to garish paintings on black velvet, Mohegan Sun is actually restrained. It does not overpromise. It does not pour its empty apocalyptic sadness all over you.

No, if there were ever a way to create a casino that paid sincere homage to Native American heritage while also housing 2,500 slot machines, this place had achieved it. First of all, the entire gaming area was made to look like a colossal, multi-acre wigwam. The superstructure of the place was made with, or buttressed by, enormous trees, stripped of their bark, their volume speaking of the persistence of life through centuries of struggle, their skins buttery and smooth. There were animal skins stretched and hung from the rafters, from enclaves, everywhere, and always there was an amber light murmuring pleasantly from behind. It was ravishing, all of it, but I know, as you know, that we can't think of this being ravishing. We all know in our hearts that slot machines are great-looking machines, but we have to think they are not great-looking machines because they are slot machines and they vacuum people's money. We know that casinos are beautiful, too, intricate mosaics of glass and silver and crimsons, and white, heavenly lights, but because they are probably morally unhinged and depraved, casinos are not given any credit for any of this.

Mickey Thomas performing with Starship in 2012. Photograph: Rex/Features

Through the doors, young people were streaming in, all of them dressed for a special night out. None were wearing shorts or T-shirts or baseball caps. All the men were wearing button-downs and their hair was tidy, and all the women were in heels and dresses. They were coming to the casino owned by the formerly subjugated Native American tribe and they were hoping for a nice night out, hoping to have a drink, play some games, hear some music by the band called Starship. And, here, Mohegan Sun seemed to have achieved the ultimate goal of all casinos: attracting and cultivating an easy mix of live entertainment, a certain amount of glamour, and a well-dressed and polite clientele. I was having a great time, and the band had yet to begin. I found a stool at the bar, near the sound-mixer, with a clear view of the stage and the people watching it.

The concert area was roughly a circle, a casually fenced-in area in the midst of the rest of the casino, and on the floor were about 50 tables, each seating between four and eight people, all of them talking, drinking, looking to each other, but also glancing every few seconds at the stage, not wanting to miss the entrance of the band. The audience was both what we would expect and, then again, every other table defied assumption. Yes, there were the many tables of older women, out for a girls' night to hear the songs of their youth, sung by a handsome man their age wearing snug pants. But then next to their table were a pair of glamorous couples in what seemed to be ballroom-dancing outfits. Then, next to them and just before the stage, I saw something I did not expect: a trio of tables occupied by adults with various disabilities. Some were in wheelchairs, some on crutches, some were adults with Down's syndrome, and with them were a few care workers, and these helpers were as excited, or probably more so, as those they were helping, or anyone else in the audience for that matter.

They all looked up to the stage in front of them, which was roughly a half-circle, meant to seem like it had been carved out of the tip of a rocky mountain, its peak near the top of the wigwam. On the mountain were a few stuffed or fully fake wolves, standing still, and on either side of the mountain there were screens, which were showing footage of wolves walking, running through heavy snow and howling. I was trying to figure out why there were wolves everywhere – ah, the place is called the Wolf Den! – when the band stepped on to the stage. There was not much fanfare. The stage had no curtain, after all, and the room couldn't be darkened like a normal theatre might, given it was in the middle of the casino. So the band just walked on to the stage, then Julie walked on to the stage, then Mickey, the lights came up slowly, and the audience cheered and whistled, and at least a few people who had been sitting were now standing, clapping and jumping, then sat down again.

The band waved, picked up their instruments and began. Julie was holding a tambourine, which I thought one of the funniest things I'd ever seen, because I'd never seen her or anyone I know holding a tambourine, and took the tambourine as a universal symbol of someone on stage who had nothing else to do. The tambourine added to the strangeness of seeing Julie there at all. I had known Julie for many years, usually in the context of her playing small venues with her loud band, or in the context of the bar where she worked, all her usual environments gritty and without fanfare or polish, in neighbourhoods of San Francisco where the people were young and rode motorcycles, and were not just pretending to be broke but were often actually broke.

Now she was in Connecticut, on stage with a band that had been around, in some form or another, since before she was born. Julie's own band played dissonant music that she'd written by shredding her soul and then digging into the shredder, finding some threads and trying to arrange them into songs of minor notes and angst, and now Julie was at the Mohegan Sun Resort Casino, and to everyone in the audience, she was simply a member of Starship. Few, if any, of the audience members could have imagined that she had been recruited, desperately and at the last minute, then flown in, quickly trained, and would be gone shortly after this gig. But this is the way with music and musicians, and it's something I've been forever fascinated by – their ability to blend in with each other, instantly, like two rivers meeting and entwining and quickly becoming one. Get a band together and add 100 guitars and it sounds the same, it sounds like everyone knows what they're doing. And looking up at Julie onstage, holding her tambourine, she seemed very happy, and confident that she could be part of this music with these strangers this night.

Starship's first song that night was "Nothing's Gonna Stop Us Now", a big hit they had in 1987, a song commissioned for the soundtrack to the movie Mannequin, starring Andrew McCarthy and Kim Cattrall, and centred around the latter's transition from a mannequin admired by the former to an actual woman and actually in love with Mr McCarthy's character. The crowd loved the song, swaying to its mid-tempo beat, squealing here and there when Mickey made a sensual manoeuvre or two. After the song wrapped up, someone yelled out "Where's Grace Slick?" – this person seemed to genuinely want to know the answer. I can't remember what Mickey said in response, and I can't remember the exact order of the songs they played shortly after that. I do know that they played "Sara", a ballad that had been a No 1 hit around the world, and that Mickey did "Fooled Around and Fell in Love", a song he sang for another group, the Elvin Bishop Band, back in 1978.

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And while they played, I watched the band, scanning from one member to the next and a few things became clear. First of all, they were all consummately skilled – not unexpected for session and touring musicians – but more surprising than their ability to make every song sound exactly as it had on the recording was that they were having a blast. The band, who one might have assumed would be blase, even outright bored, playing these old songs for the thousandth time, were not only playing with professionalism, but they were moving with great feeling, feeding off the energy of the audience, which was pure and loud and was about to get out of control. Mickey was having a visibly good time, and, during those first four or five songs, was trying mightily to get as many people dancing as possible. Between lyrics, between songs, he admonished anyone who was not dancing. "C'mon, people, this is a party!" He was having middling luck getting the non-dancers dancing until the first notes of "We Built This City", when, almost immediately, the entire audience was on its feet. If you don't remember the song, it starts with the title, the words coming obliquely from left to right, as if descending from outer space on some echo escalator: "We built this city / We built this city on rock'n'roll."

Then the music kicks in, a thumpy synthesiser groove. By this time, just after Mickey sang the first words, the entire crowd was on its feet and was flooding toward the stage. It looked almost precisely like the scene in the movie where the underdog band wins over the tough audience who instantly go from sceptical frowns and bored postures to ecstatic dancing, everyone convinced that there was no better band, no better music and no better place on the planet to be than there. This was actually happening, here, a few seconds into the song. The ballroom dancers were up and were executing precision moves, and were soon switching partners with the disabled folks, and everyone seemed suddenly to have known everyone else in the casino for years and knew that interpersonal heat. The care workers were up and flailing, the people on crutches were up and spinning carefully, and because everyone was so familiar with each other and mixing so freely I had the fleeting thought that maybe this was a family reunion, and found myself involuntarily looking at the screen above, for a clue, a sign that might say "Hightower Family Reunion" – but found only the howling wolf again, now ankle-deep in snow.

The song was cooking along, and everyone was watching Mickey, who was singing with the microphone cord in one hand, and for a second it seemed like the audience was moving around in a moat, Mickey the tower above them. Every so often they looked up to Mickey, and then back to each other with eyes that said: "Can you believe this?" Mickey moved from one side of the stage to the other, sharing himself with not too much movement, and nothing quick or exuberant – just a few steps one way, a few the other, stopping for the chorus, at which point he would make fists of his hands and squeeze them in front of his torso and lean back a bit to belt the words forth. The dancers in the audience awaited the chorus and exploded when it came. Every time it was almost there – "Don't you re-mem-ber …" then a few downbeats then a quiet, pre-chorus, "We built this city … We built this city on … rock'n'roll!" – the suspense was murderous. Then, twice as loud:

"We built this city!

We built this city on rock'n'roll!

Built this city!

Built this city on rock'n'roll!"

And everyone's arms were shooting into the air, pumping with each syllable. And the chorus kept coming – eight, nine, 10 times! The band was milking it and the arms shot up again and again. Good Lord, we all thought, that is a great chorus. But then again, what did it mean? What city was built by rock'n'roll? Was it an actual city they were talking about? Starship was from where – Marin County, I think. Jefferson Airplane was from San Francisco, but Starship was from Mill Valley … Was it Mill Valley that was built by rock'n'roll? The song made little sense. The rest of the words didn't seem to add up to much but, unconsciously, everyone in the audience was attributing its message to our own cities, imagining that our hometowns were built by rock'n'roll, and imagining or assuming that this was a good thing, to create a city's foundation out of rock music, just as Sydney, Australia – wasn't it Sydney? – had created their foundation by using overturned trees jammed into the clay of the bay. Or maybe it was this city, Mohegan Sun, that was built on rock'n'roll? It was better than being built by genocide or nuclear power, right?

The Mohegan Sun casino, where Starship played in 1999. Photograph: Mario Tama/Getty Images North America

I tried to think of a time when I'd seen so many people so happy all at once. I'd been to maybe 100 concerts at that point, and had seen placid enjoyment, mass head-nodding, knee‑bending, a dull contentment made possible with beer or pot. But people nodding their heads at indie rock shows were not happy this way. People twirling at funk-rock shows were not happy this way. This was different. This was unconscious. This was subconscious. These people at Mohegan Sun were not even drunk; they were dancing in front of the stage, mostly sober – had I ever known anyone who could or would dance sober? I was still in the back, by the bar, but I was jumping up and down, and the rest of the bar was jumping up and down, everyone's face positively stupid. And it occurred to me then that fun is only fun when it's stupid. That there is no joy without stupidity, without abandon, without judgment – that music is best enjoyed in this stupid way, in a stupid place like this, with people you love holding stupid tambourines and playing with strangers amid strangers, who are dancing around to a song about spaceship-people building municipalities without permits or city planners but with pop songs.

The song continued, longer than the recording, the chorus coming again and again, the hands flailing, the faces astonished, the feet jerking all over the place. Even Julie, who was a Serious Indie Musician and Songwriter, was having fun. She was playing her tambourine, and mugging for the crowd, and pogo-ing during the chorus, and whipping the crowd into a new level of frenzy. The wolves on the screen continued to hunt in the snow, and the teepee above us continued to be both vaguely offensive and absolutely beautiful and historically reverent, and the song continued, on and on. Everyone was having such fun that, when the encore came, the band played the song again. To be clear: in a 42-minute set, Starship played the same song, "We Built This City", twice.

And why not?

And here it's important to note that all of history is broken. It's important to note that everything we humans do is messy. It's important to note that we are makers of mistakes, a billion mistakes every day. Most of what we do is wrong, we have to admit this – most of what we do is utterly wrong. We make colossal blunders, then small corrections, then more mistakes, more small corrections. Sometimes we learn, usually we don't. But then every so often we create a little joy. Every so often someone creates a perfect pop song, and then people can come and hear it being played, even in an Native American casino built on land stolen and restolen over and over again, by a band far past its creative prime, simply because if they do, before we are too old to do so, before we all die, before the United States crumbles in on itself, people will forget all our mistakes, national and personal, for a second or two, and will dance our ugly selves stupid.

• This essay will appear in Dave Eggers's forthcoming travel collection, Visitants (Hamish Hamilton).