Green Day’s “Good Riddance (Time of Your Life)” was released Dec. 2, 1997, but the poignant ballad could have come out several years earlier.

Frontman Billie Joe Armstrong originally began working on the tune during the group’s early days. Sometime around 1991, he’d fallen for a woman named Amanda who frequented the Bay Area’s Gilman Street music scene. She was a feminist and a rebel, and eventually she broke Armstrong’s heart. Amanda dumped him and moved to Ecuador. Some said it was to be with family; others claim she joined the Peace Corps. Whatever the reason, the experience inspired the young Armstrong.

“I went to this house party in Berkeley, where all these college students were passing an acoustic guitar around and singing songs — a ‘weird dudes with ponytails and an acoustic guitar’ kind of moment,” Armstrong later told Rolling Stone. “I remember going, ‘Oh, man, I should try doing an acoustic song,’ so I wrote that song about her and the end of our relationship.”

The deeply personal “Good Riddance was a far cry from the loud, frenetic punk music Green Day was cranking out at the time. As such, Armstrong initially opted to hide the song from bandmates Tre Cool and Mike Dirnt. In fact, he refused to even bring it up until the recording sessions for 1994’s Dookie.

"We didn't put it on Dookie because it didn't fit," producer Rob Cavallo said in the book Nobody Likes You, "and we said, ‘Well this doesn't really fit. We think it's a great song, but it doesn't really fit the album.’”

A similar conversation would take place during the sessions for 1995’s Insomniac, as Green Day considered and once again rejected “Good Riddance.”

“I didn’t think it was going to be for Green Day at all,” Armstrong told Rolling Stone. “Then when we were doing Insomniac, I did a demo for it, but it wasn’t right for that album, either. I didn’t really know what to do.”

Finally, during sessions for 1997’s Nimrod, Green Day determined they were ready to give “Good Riddance” a try. It had been some six years after the song began to take shape.

“It took quite a while actually to figure out how to arrange that song and structure it,” Cavallo said in Nobody Likes You. “I played around with it for a couple of months before we went in the studio because I was like, ‘Oh my God, I know this song’s a hit, but we just have to figure out how to do it. How do we do this song?’ And when it came time for Nimrod, Billie said, ‘I think this song will finally fit.’”

Listen to 'Good Riddance (Time of Your Life)'

Cavallo suggested one important addition. “Then I thought to myself, ‘You know, the one thing that the song really needs is strings,’” he added. “When I brought the idea to them, they said, ‘Strings? Are you sure?’ and I said, ‘I think so. I think it's what the song really wants.’ They said, ‘Well, OK, we'll fuckin’ try it then.’ They were definitely open to it, but it was a risk.”

In the end, “Good Riddance (Time of Your Life)” essentially became an Armstrong solo track, as his voice and acoustic guitar were the only other instruments on the song. It was deeply personal, sorrowful in tone and undisputedly catchy. It was also dramatically different from any other Green Day song.

“Probably the most punk thing we could have done is put that on the record at that point,” Dirnt later told VH1, noting the band’s refusal to be boxed into a certain sound.

“It was amazing,” Armstrong told Rolling Stone. “It opened up a brand-new world: ‘Oh, fuck, we can do so much more.’”

Released as the second single from Nimrod, “Good Riddance (Time of Your Life)” became a multi-platinum smash. Beyond chart success, the song also became a cultural benchmark of the late-’90s. “Good Riddance” was everywhere, soundtracking everything from the World Series to the final episode of Seinfeld.

“It took on a life of its own,” Armstrong added. “I was definitely not thinking about weddings and graduations when I wrote it.” Cool later admitted that “you never expected to write anybody’s prom fucking song. You never even got invited to your prom!”

Decades later, “Good Riddance” remains one of Green Day’s most beloved songs. Just as important as its popularity, the song emboldened the band to venture further beyond their punk-rock comfort zone. It’s fair to assume the world would never have heard such bold endeavors as American Idiot and 21st Century Breakdown had Green Day continued to keep “Good Riddance” on the shelf.

"I was scared for that song to come out," Armstrong said in Nobody Likes You, "and I was really excited at the same time. I thought it was a powerful song and it made me cry and all that, but there was just that fear of it coming out – and I never had that feeling of being afraid.

"But because it was such a vulnerable song," he added, "to put that song out and it was like which way will it end up going? It was really exciting and it kind of sparked more in us as songwriters to expand on that."

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