When Yellowcard took the stage at last month’s APMAs to accept the inaugural Vans “Off The Wall” Award and, later, bring the house down with a colossal, career-spanning musical performance, it was a supremely bittersweet moment—another entry into a seemingly mile-long list of lasts the band will be experiencing over the next seven months. In June, Yellowcard announced they’d be breaking up after nearly 20 years, but not before commemorating their career with an expansive world tour and a final, self-titled album, due out Sept. 30 on Hopeless Records.

It was not easy to do, of course,” says vocalist Ryan Key of the decision to put Yellowcard to rest. “Some of the reasons are kind of personal, so it’s hard to spell out everything that went into the decision. It was a long process of coming to terms with why this needed to happen and how it was going to happen. The important thing is we got to a place where we knew this was the direction it was going to go, and we wanted to take advantage of the opportunity to do it our way and plan it out step by step.”

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Doing it their way is what got Yellowcard to this point in the first place. Sure, the band were able to mine the pop-punk gold rush of the early ’00s to platinum success on Ocean Avenue, but they were never afraid to zig when their peers zagged. Instead of churning out a dozen more sun-kissed pop-punk songs for the TRL masses, the band eschewed the formula on 2006’s Lights And Sounds in favor of razor-sharp alt-rock—along with the occasional orchestra, trumpet solo and duet with a Dixie Chick. That sense of fearlessness and experimentation continued well into Yellowcard’s second act, too: Following a two-year hiatus after the touring cycle for 2007’s Paper Walls and a pair of albums to reclaim their sea legs (2011’s When You’re Through Thinking, Say Yes and 2012’s Southern Air), the band once again shot for the stars on 2014’s Lift A Sail, a slab of experimental melodic rock imbued with electronic flourishes.

Produced by Key and guitarist Ryan Mendez—with longtime mentor Neal Avron serving as executive producer—the band’s swan song is a fitting ending to an accomplished career, a record that culls together moments from virtually every one of the band’s albums into a final set. From frantic pop-punk (“Got Yours”) and hooky pop-rock (“A Place We Set Afire”) to sturdy alt-rock (the aptly titled “Rest In Peace”) and folksy campfire balladry (“I’m A Wrecking Ball”), Yellowcard is a poignant, perfect encapsulation of where the band have been—and, perhaps more importantly, where they are now.

“With Lift A Sail, we went into it wanting to experiment and try something new to have fun and push ourselves, but we didn’t do anything on this record that wasn’t exactly what we wanted to do,” Mendez explains. “Let’s put every riff we think sounds great on there. There are a couple of lengthy songs on there. Can we do a song where the bridge is two-and-a-half minutes of guitar noises? Why not? It’s the last chance we have to do it, so we wrote exactly what we wanted to write—not that we haven’t in the past, but maybe in the past we made a decision here or there based on radio. There was no agenda this time besides [to] do what feels good.”

The sense of finality led Key to approach writing Yellowcard from a different angle lyrically, as well. The singer felt especially galvanized by the ability to have the album’s lyrics serve as his farewell to friends, fans and family, and he challenged himself to use each song to express a different sentiment of saying goodbye. Some, like the affecting wistfulness of “Empty Street” (“Boxing up the fireworks/cancel my parade/the street is empty tonight”) and album closer “Fields & Fences,” complete with a goosebump-inducing orchestral outro, find him staring down his rapidly approaching future as Yellowcard’s ex-frontman, while the fiery “Savior’s Robes”—with its biting chorus, “Play us a song I know/Make it an older one”—seems aimed at those who’d prefer the band’s Ocean Avenue selves be fossilized forever.

“It actually really helped me as a writer to have that focus,” Key says. “I don’t remember the last time I wrote a record with a mission ahead of time. With Lift A Sail, I knew it was going to be heavy but didn’t know how it was going to pan out. This time, I knew I wanted to try this to see if I could pull it off. Some of it is very loving and reflective, some of it is angry, some of it is ‘I don’t want to stop, but I know I have to.’ Having it be the final record really lent itself to writing that way.”

There are certainly regrets over the years: The band admit the jump to Razor & Tie for Lift A Sail—a move done almost exclusively with another shot at radio in mind—was probably an unnecessary decision. You get the sense they realize they never should have left Hopeless Records, but Key and co. learned long ago there’s no use dwelling on mistakes. It’s that forward-thinking mentality that kept them going through the leaner years, when other bands with their same level of past success might have schemed behind the scenes to reclaim glory days gone by. And it’s what prevented ego from getting in the way of opportunities like a 2011 tour slot opening for All Time Low, a band who worshipped at the altar of Ocean Avenue back in the day, but had ballooned in popularity by the time Yellowcard returned from hiatus.

“By the time Southern Air came along, it kind of felt like we never left,” violinist Sean Mackin says. “We had some tours with some youthful bands that kind of jump-started the Yellowcard career again. We truly had a second chance and went so many amazing places we didn’t go the first time around.”

“Our band has gone from being all the way at the top of the game and kind of crashing down to a point where you need to take some time away from it,” Key adds. “It’s a conscious choice every day not to live in the past and wonder, ‘What if we had done this or that differently? Would we have maintained that Ocean Avenue success for longer or sold more records?’ I think between putting out so much music and touring our asses off for the past five or six years, it hasn’t been hard to make that choice. There are a lot of bands that don’t get the opportunities we’ve had once, let alone twice. You have to be humble and not let yourself get stuck in ‘coulda shoulda woulda.’”

When asked their favorite moments of Yellowcard’s career, the answers are wide-ranging. Key holds the group’s 2004 MTV Video Music Award in high regard, while Mendez and bassist Josh Portman recall standout shows in Japan and Africa, respectively. For Mackin, his proudest moment isn’t even really a professional one: “It was a pretty big deal in my family when I dropped out of college,” he says. “There was some unrest in the relationship with me and my mom. She always recited, ‘If you want to live in my house, you’ll play the violin. One day you’ll understand. This is a gift.’ Being able to call her one afternoon in 2004 and say, ‘Hey, mom, just wanted to check in and let you know we sold a million records. I play violin because of you, and you didn’t like the path I chose, but we made something of ourselves’ ... that was a real special moment for me and my family.”

There are still plenty of special moments to come as Yellowcard embark on their victory lap around the world, a 50-plus date tour that kicks off in North America in October and snakes its way through Europe, the UK, Australia and Japan well into next year. Those hoping for a reunion with estranged drummer Longineu Parsons will be disappointed, but the group have enlisted the help of Like Torches drummer Jimmy Brunkvist, whose band will accompany Yellowcard for much of the farewell tour. They’ve already prepped a massive 25-song setlist, which they promise will span nearly every album since Key assumed the role of frontman in 1999 and includes deep cuts, B-sides, new songs and, yes, plenty of fan favorites.

QUIZ: How well do you know the lyrics to “Ocean Avenue”?

There will undoubtedly be more than a few tears shed, both in the crowd and onstage, as the days get checked off and the number of shows begins to dwindle. But even though the end is near, it’s best to treat the end of Yellowcard less like a funeral procession and more like a celebration: As Key notes, some bands never get a second chance at all, let alone one as productive and successful as Yellowcard have enjoyed since returning from hiatus.

“There’s not really a way to fully acknowledge how grateful we are, whether it’s for people who have supported the band throughout our career or the fans around the world who have given us this opportunity, time and again,” he says. “We know how small the odds of being a successful artist for this long are—they’re not good. There’s been a lot of pinch-yourself moments throughout our career, and that’s thanks to the fans. We’re really lucky.”

They never did have another radio hit or recapture that mainstream success, but that’s not what this was really all about in the end. Yellowcard’s second act was about the band being true to themselves, about embracing their past while striving for a brighter future. The band’s fans realized this, too, and they honored Yellowcard with staunch loyalty that will exist long after the last notes of “Ocean Avenue” ring out in some sweaty rock club next March. When the curtain finally falls on their career, Yellowcard will go down as one of the most revered pop-punk band of the modern era—not bad for a group of kids from Florida with a record deal and a violin.