It fucking worked perfectly during soundcheck.

And now, when the critical moment hits, limpidly, hysterically — maybe even appropriately — the shit’s just taking way longer than expected. People along the aisles crane their necks. Those in the balcony lean forward, iPhones out. Everyone wonders what’s going on, ultimately trusting that this stunt will be worth it.

With Guster, the reveal is almost always worth the wait. And at the moment, Big Friend, the band’s lovable-yet-mysteriously-unsettling massive inflatable mascot, is slow to inflate. Like, two-minutes-too-slow. This was going to be poetically and symbolically perfect. Guster at Beacon Theater the day after Thanksgiving, playing to a sold out crowd in celebration of their two-and-a-half decades as a band. A 25-songs-for-25-years set crafted with fan favorites, for-the-hardcores rarities and appropriate nods to every iteration of the band’s portage trail to this night. The culmination was to come at the start of a rare second encore, during a poignant, guitar/vocal-only performance of “Parachute” — one of the first songs, and still among the very best, the band ever wrote.

The droll Brian Rosenworcel, drummer and percussionist, emerges from side stage, mid-song, to unpack and plug in Big Friend.

Then … he just stands there. We all do. And wait, wait for the emblematic crescendo from a furry creature in blow-up nylon form. Anxiety turns to amusing awkwardness. Rosenworcel simpers as he implores bandmates Ryan Miller and Adam Gardner to vamp. We can still pull this off!

There is no vamp. The song ends. Big Friend is a blob of disappointment.

“GOD DAMMIT!” Rosenworcel half-jokingly screams as “Parachute” comes to a landing.

“I just want you to know,” a chagrined Miller then tells the amused crowd, ”after 25 years, we still got it, guys.”

Within a minute of the song finishing and the trio prepping for the next tune, Big Friend is … suddenly big! Inflation has reached completion. Quintessential Guster.

Guster: the band that invented a word. A word that transformed to a proper noun for a group who became defined by decades of nimble alt-pop songwriting and an essence of being one of the most fan-friendly and relatable bands to hit the American mainstream the past two decades. More people than you realize know of and still listen to Guster. Ask a friend; you’ll see. Still, they’re one of the most underrated, under-discussed bands of the past two decades, a group liked by many but only truly, endlessly loved by a concentrated faction that has helped pushed this group to continue to make music and do it on their own terms.

This is an abridged story of how they aligned on a fluke, managed to make music for 25 years — and only recently decided to keep growing and going.

Scene: sub-freezing temperatures outside a blue dumpster in Pittsburgh on a January afternoon. The glamour level is lower than the mercury reading.

Snow underfoot, Guster is playing a show to 11 people.

The impromptu four-song set came about in early 2016 after the band had a show in Philly cancelled due to a blizzard. Stuck four hours west, in the Steel City, they figured, Why not? Let’s literally play in front of garbage. The over/under on other established bands that would do this is set at 0.5 (and I am taking the under). This was one of the most simplistically charming things I’ve seen any band do at any level. Especially in a cynical social media era, when so many viral videos and photos could double as clever PR tricks.

That embraceable work ethic and down-to-earth attitude is what’s allowed Guster to comfortably thrive on their own accord.
“There’s an approachability that’s there,” Miller said. “There’s not a pretension that’s there. There’s a sense of humor that’s been pretty pervasive throughout, a sense ‘They don’t take themselves too seriously.’”

You don’t have to idolize your music heroes. I’ve found, often times, the groups and artists many people stick with well beyond their teen years and into their late 20s, 30s and 40s are the ones who truly enable a connection with their fan base. With Guster, there’s a link from interpersonal communication through song that extends to the personality of the band and its members. Guster’s appeal with tens of thousands of their supporters stems from the notion that Rosenworcel, Gardner, Miller (and recent fourth full-time member addition Luke Reynolds) could be your friend, that they really are your friends. Funny guys with a crazy-good knack for melody and harmony who happen to be in a band.

Guster is the most affable, personable, enjoyable alt-pop group of the past two decades. They are not an acquired taste. You “get” them pretty quickly. Check out the dark groove of “Airport Song,” the awesome vocal interplay on “What You Wish For.” “Careful” could have been written in 1976. “Dear Valentine,” off Ganging Up on the Sun, for my money, is one of the best deep cuts on any pop record of the 2000s. Recent LPs have featured sonic exploration with great results, like “On the Ocean,” “Expectation” and “Lazy Love.” They mostly write digestible but layered pop songs that underscore their understated adaptability and underrated sonic prowess. Every record has been a natural modification of the band’s sound and songwriting, and that’s not boilerplate praise. Listen to the records; their modification is undeniable. They were never one-, two- or three-hit wonders. They’ve never won a Grammy. Because of this, it’s easy to claim that Guster’s become one of the most under-appreciated pop acts of the past two decades.

I’ll claim just that.

Guster was born from long-shot odds. If alternate universes exist, Guster doesn’t subsist in any of them. Over the years, the most undersold aspect of the group is how unlikely it was these guys even met, let alone formed a band.

Unwitting heavy life decisions catalyzed this 25-year joy ride. It’s oft-written how they were a true college band, how they met their first week at Tufts, in Boston. But Boston is the densest college city in America. Any of them could have just as easily loved Beantown and picked a different school in the city. And aside from a couple of world-renowned institutions, a majority of college kids patrolling Boston every fall are within a three-hour drive of home. Yet none of the guys in Guster are from Massachusetts. Rosenworcel had desperate hopes of going to Brown but was rejected. Gardner was casual and carefree about picking a college, and really didn’t even know anything about the school. He just wanted out of New Vernon, New Jersey, where the horse trails outnumbered the paved roads.

“I don’t even remember loving Tufts and thinking, This is it,” Gardner said. “The irony is, my entire life unfolded from Tufts. I also met my wife there, I met the people I run Reverb with there.”

And in the 164-year history of Tufts, the percentage of people who’ve attended that had upbringings in greater Dallas is probably hovering at 0.1, but Miller’s one of them. He only wound up at Tufts because he loved LEGO as a child, dreamed of getting into MIT for engineering, and by the time he left for school, Tufts fit into his ideal of studying in New England.

All of those decisions had to collide, and even then, the only reason why Miller was keen on the trio forming an act was because they’d all played in bands in high school. An eager, 18-year-old Rosenworcel was so set on making it work, he’d haul his ass from one end of the campus to the other. Long before they were Guster, they were Gus, and before that, they were “Ryan, Adam and Brian,” teenagers playing the Hotung Cafe and stumbling through Paul Simon and Toad the Wet Sprocket covers.

“Ryan and Adam lived ‘uphill’ freshman year and I lived ‘downhill’ — worlds apart,” Rosenworcel said. “I made a very concerted effort to get in on their acoustic project. Sophomore year, me and Ryan decided to room together in 217 Bush Hall and the band really grew from that.”

The band was funded throughout college by their parents. They sold tapes on the streets of Cambridge, and eventually the open-air Harvard Square performances grew too large. As they worked their way toward graduation, Guster became one of the biggest grassroots bands in Boston’s history. Miller still keeps those origins close, as the early ‘90s still remain a pillar of the band’s staying power.

“Being a college band is a huge part of our history,” he said. “We couldn’t have done this if we lived in Brooklyn and waited tables.”

The day after they graduated, they had their van, minimal equipment and no idea if this was going to turn into something bigger. They chose to drive, kept moving and haven’t stopped since.
What are the critical decisions that occur over the course of a band’s run that allow it to continue for 25 years? Lasting that long without a hiatus, outright breakup or accidental disbanding is 1-percent territory in the music world.

“To me, I think it’s a lot of things that make a marriage work,” Gardner said. “It’s respect for each other, good communication, I think it’s really important for us to check our egos. I think that stuff can break up bands. The first thing is a feeling that we continue to make, once you get past those basic ones, once you get into the double-decades, it’s the mutual feeling that we still have more to create together.”

For the uninitiated, 1999’s Lost and Gone Forever is the gateway Guster LP. Be it with records that came before or after, all the band’s rivers curl back to that album. The group got famous for three things: incredible harmonies; all-acoustic ingenuity that sounded more intricate and bigger than a three-piece; and having a dark-haired, lanky Thundergod playing hand drums and, in doing so, breaking conventional thought on bands needing an orthodox drummer to cut their teeth to success.

Guster blew up the model after LAGF. For the sake of his extremities (Rosenworcel ruined his body at certain points to where he was pissing coagulated urine), he took a seat, grabbed a pair of sticks and decided to split time between percussion and a traditional kit. Gardner introduced electric guitars to his arsenal. Miller learned how to sing and play the bass at the same time. The result was 2003’s Keep It Together, which to this day feels like the band’s most colorful record.

“In the recording of Keep It Together there was some real, real ugly stuff,” Rosenworcel said. “Lost and Gone Forever was a difficult album to follow up, and the fact we were completely reinventing ourselves didn’t make it any easier. But we’ve always overcome and you only get stronger when you do.”

There is no as-yet-untold dramatic yarn of a Guster breakup or two that could have been, but the band has hit its walls and boxed its doubts.

“We’ve had a couple of dark moments,” Rosenworcel said. “The main one was, one by one we walked out of the studio on David Kahne during Easy Wonderful. It was like he broke us almost 20 years into our career and we allowed ourselves tohave that guy undermine us and it was really disappointing and the wheels stopped moving for a good while.”

The band eventually regrouped, kept portions of the pieces put together during the Kahne sessions of Easy Wonderful, and eventually finished a far superior record under the production guidance of Joe Pisapia, who was the first official fourth member of Guster, beginning in 2003. But the stress of making Easy Wonderful combined with other musical side projects led Pisapia to step away once the record was done, in 2010. This could have essentially turned into a farewell LP for the band. But it immediately found the only logical replacement in Luke Reynolds, and a new era began.

But with the writing and recording sessions of 2015’s Evermotion (Guster’s low-key stoner record and one that’s just now showing signs of aging well), the situation came to a head. For Gardner, there were genuine questions as to whether that was going to be the band’s final LP.

“Whereas before it was, ‘When are we doing it?’ he said. “The question changed a little bit. It wasn’t because the dynamic was bad — it was good — it was just a real question. We’re older now. Do we want to be doing this? If we’re at a point in our lives where we want to be doing other things, we should decide that now. I think that really hit a clear point [with Evermotion] where it wasn’t an automatic assumption that we were going to to continue to make music together.”

Many fan bases would significantly dwindle with a band who abandoned a three-prong approach to its sound that got them to where they were. Guster’s didn’t. They stayed steady, and if you go to shows now, you see plenty of college-aged fans, people who got hooked because of Easy Wonderful or Ganging Up on the Sun. Guster’s capacity to writhe their way out of being pigeonholed has been essential to their relevance as a successful standalone touring act. In their early years they were lumped with underground folk movements, but that’s a complete mislabeling. Soon thereafter, because of the festivals they played and acts they opened for, they were associated in with jam bands — but they don’t jam, and their songs don’t invite improvisation. They were never emo, never new-age punk, never ska, and their establishment in the ’90s preceded the indie-rock explosion of the early aughts, so they dodged dropping off with the dozens of other acts who came, flashed, and fizzled.

“I still don’t have a great explanation other than we’re a pop band,” Miller said. “We do right pop songs, if you really bare down [and listen]. Indie pop or rock pop, I don’t know, but I don’t bristle at that categorization at all. I don’t think we’re trying to invent anything either, and I’ve always chased the idea that we can make a classic pop record the way REM made pop records, or The Kinks made pop records, or Wilco or The Beach Boys.”

Rosenworcel sums it up with a phrase that might as well be Guster’s unofficial motto: “We know if it’s not fun, it’s not worth doing.”

“I understand there’s a lot of nostalgia and I used to resist that,” Miller told the Beacon Theater audience amid some mid-show musing.

No more.

The band doesn’t trade in nostalgia, but they do pick from that jar just enough to remind their fans they know success and sustainability is achieved through recognition of the past with a head-first approach on the future.

That night, the band invited an elderly chorus from Long Island, cutely named the Silver Chords, to sing on two songs. Near the end of the set, Miller surprised a hardcore fan from the early days, someone who’s long since cleared the bar on 200 Guster shows, to come on stage and speak to the band and the fans in attendance. Rosenworcel writes the sets, and he appropriately started the show with “What You Wish For” with just the original trio kicking off the night. The second encore also began with just the three. The details are never lost on this band nor its fan base, and that made the night so rewarding for both.

The most poignant moment of the show came after the Big Friend snafu, when they busted out “So Long,” a setlist rarity. And as they played in front of an aux mic, the band was drowned out by the capacity crowd. It was a communal moment, ironic given the song and its lyrics. But again, that’s Guster.

“I don’t know if I was able to be fully in the moment of what it meant, the 25th, and it was really more of a fun, awesome show in real time than having that huge gravity of 25 years,” Gardner said. ”I think if I let it really hit me fully, it’d be too emotional.”

Said Miller: “In some ways it felt like a great Guster show, too, which I think is a testament that it isn’t just a purely nostalgic trip.”

Not at all, and they went right up until that don’t-even-think-about-it 11 p.m. Beacon curfew. In the dressing room afterward, Miller, Gardner, Rosenworcel and Reynolds toasted to the show, to their band, to “no regrets.” They sounded enthused, satisfied, proud, like a hungry band on the verge of a first record deal. Miller giddily interjected how he thought “Barrel of a Gun” was one of their best performances of that song ever. Gardner insisted the Beacon has to be the spot they return to every Thanksgiving weekend. A renewed tradition.

“The Beacon’s always been a special venue for us,” Gardner said. ”It’s the first show of a series shows for our 25th year. It made sense that it started there.”

They managed themselves for years. They shared dorm rooms, then a house, and shipped fans band goodies in boxes of cereal. Guster built and sustained everything with humor and humility. They’ve gotten older, but this doesn’t feel like an aging band. The plan was never for a one-night-only celebration. This 25th anniversary will bleed into 2017, headlined by a four-night Jan. 12-15 run at the Paradise Rock Club in Boston, which was the first legitimate venue to give Guster a chance. They’ll be honoring their fans and the band’s legacy many more times, but appropriately enough, the plan is to have a new album released before the year expires; 2017 will be Guster’s 26th year, and they sound eager to move their sound forward again.

“I’m fucking reflective every day,” Miller said. “Every time we step out on the stage, when we tour. Do people care? I’ve had all kinds of psychic breaks an internal breaks and what are we even doing? Is this even fun? Can we make music anymore? Those conversations happen constantly. Fortunately we’ve come around where we’re in a good place. I’m buoyed by the joy of the room. The energy in the room. The shows don’t feel overly nostalgic. They feel very visceral. … I’ve heard the team ‘cult band’ thrown around with us, which I don’t take as pejorative at all. If I sit here and play and think about what we’ve done and where we are, it’s fucking incredible.“

Watch this and you’ll see where Miller is coming from, what the band built and why, if it’s not fun, it’s not worth doing.