Love them or hate them, many of the songs that Glenn Frey recorded with the Eagles deserve the term “timeless.” “Hotel California” will long haunt pop culture, whether via American Horror Story episodes or on Frank Ocean albums. It’s hard to conceive of a karaoke night where songs like “Tequila Sunrise” aren’t performed. And “Take It Easy” will keep seeping into the consciousness of young people who may have no idea that it helped define the ’70s; already, the song feels so elemental that it can be strange to think of it as tied to a particular time and place at all.

The above can’t easily be said for Frey’s solo hits in the 1980s, a fact that somehow makes those songs feel more poignant in the wake of Frey’s death Monday at age 67. Frey is usually seen as the leader of the Eagles, and he and Don Henley have said they deserve the bulk of the credit for the band’s hits. But after a famously contentious Long Beach concert in 1980, Frey reportedly initiated, and then savored, their breakup. “After you work at something for nine years, you kind of want to be your own boss,” he told People ​afterwards. He explained in a different interview that he titled his 1982 solo debut No Fun Aloud because “I had a lot of fun doing it, and I wanted people to have a lot of fun listening to it.”

Juxtaposing the Eagles’ late ’70s hits—say, “Heartache Tonight”—with No Fun Aloud’s first single “The One You Love” feels like time traveling between decades. The syrupy sax, the pillowy electric piano, the steady ballad rhythm, Frey’s supremely tender, unaccompanied performance—whatever this sound is, it isn’t carefree California country-rock of the kind that made the Eagles famous.

No Fun Aloud went gold, but it was a few more years before Frey’s career truly entered a near-iconic second act. The singles “The Heat Is On” (1984) and “You Belong to the City” (1985) both arrived on epochal soundtracks—Beverly Hill Cop and Miami Vice, respectively. The songs are perfect time capsules, defined by lite-jazz sax peals, guitar riffs that are no less pulse-raising for sounding chintzy today, and Frey somehow growling while crooning.

Frey licensed “You Belong to the City” for an extended-length Pepsi commercial that he also starred in, which was neither the first or last time his work annoyed people who believe that rock and capitalism shouldn’t embrace each other too enthusiastically. “If Little Steven and Neil Young don’t like me doing Pepsi commercials, I trade insults at 40 paces,” Frey said in his defense in 1988, according to a fan site. “When has integrity ever been synonymous with rock ‘n’ roll?” The statement might sound extraordinarily mercenary, but it was also refreshingly honest coming from from a hitmaker. Cameron Crowe’s 1975 Rolling Stone cover story on the Eagles featured lots of quotes from Frey and Henley about carefully planning their career and contriving ways to remain relevant; rather than later back away from those statements, the pair remained loud and proud about the fact that their high ambition was matched by their own abilities.

Frey’s second album, 1984’s The Allnighter, produced another successful single that’s become a trademark of its era: “Smuggler’s Blues,” which inspired an episode of Miami Vice that Frey also starred in.

That show has become a surprisingly important musical touchstone in the new millennium. When people today say a song sounds like Miami Vice, they’re in part noting how it sounds like Frey’s ’80s work. Taylor Swift’s 1989 bears the marks of someone who rifled through his solo hits; so does M83’s “Midnight City,” the music from lots of artists in the indie “chillwave” movement that crested a couple years back, and of course, the beloved Grand Theft Auto: Vice City soundtrack. If this particular era’s music isn’t timeless per se, it’s in part because of dated studio tricks—gated drums, now-obsolete keyboards, saxophone used in ways seemingly scientifically engineered to inspire backlash. When artists today throwback to those production choices, it’s necessarily with a wink, deliberately tapping into shared nostalgia. But it also often accompanies the kind of earnest, straining feeling that was a speciality of Frey’s.

“Smuggler’s Blues” is also remarkable for its lyrics about the intractability of the international drug trade, an issue that was very much of its era but obviously remains relevant today. Like many of Frey’s songs, it was a narrative; unlike most of his or anyone’s, it has a complex political message. Frey and Henley both talked a lot about how much they sweated on the words to their songs, and you can see that work in the economy and directness of “Smuggler’s Blues”:

I knew the gun was loaded
But I didn’t think he’d kill
Everything exploded, and the blood began to spill

Pop doesn’t produce many songs like this these days, with un-mushy subject matter (Robert Christgau’s review called it “non-DSMR”) discussed without ironic layering or meta references. The bluntness may scan as cheesy today, but it’s also part of its novelty and appeal. Of course, Frey could and did create music that was more obtuse and mysterious—“Hotel California,” also about drugs, is the ultimate example. But “Smuggler’s Blues” was written and recorded for a different era and it served it well, which is all Frey ever really wanted to do. At one point in the ’90s, he reflected on the idea of relevance and legacy: “What happens is, if you make music for your time, and you do it well enough, sometimes it becomes music for all time.”