Year after year, Pitchfork Music Festival proves to be one of the most celebrated music festivals in the country. Its small size gives it a leisurely feel (the three-day festival in Chicago’s Union Park draws an estimated 50,000 attendees compared Lollapalooza’s 300,000 in Grant Park). Vendors help support the local economy, and the lineup is always — what’s the word? — eclectic. It’s a reflection of the acts praised by the Pitchfork taste arbiters in the months leading up to the annual festival.

In his new book But What If We’re Wrong?, Chuck Klosterman questions the idea of "merit" (being worthy of praise) as reliable criteria for the longevity of culture – books, movies, etc.

In the broadest sense, merit does play a key role: The work has to be good enough to enter the critical conversation, whatever that conversation happens to be. But once something is safely inside the walls of that discussion, the relative merits of its content matters much less.

In other words, what critics are praising today isn't necessarily going to be what we're listening to 50 years from now. It's surprising that Klosterman — a contemporary pop culture writer with dozens of essays about music published by Rolling Stone, Spin and the like — fails to apply this question to music. So I’m going to.

Today, Pet Sounds — which Brian Wilson performed front-to-back at Pitchfork — is regarded as a towering masterpiece. How did it achieve that status, though? Was it because of the album's critical acclaim, its popular success, or both? Would Wilson be selling out arenas if the Beach Boys were merely critics' darlings?

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Curation — of a music festival lineup, for example — also informs longevity. Much like Klosterman thought after first seeing a building designed by well-respected architect Frank Lloyd Wright, devoted Pitchfork followers either think, “This is what brilliance sounds like,” or “This is what Pitchfork recognizes as brilliance,” when the lineup is announced.

When a pop singer-songwriter who got her start on Canadian Idol and has sold more than 20 million records worldwide opens for Beach House, it contextualizes Carly Rae Jepsen’s seemingly straight-up pop tracks: we hear the music differently than we would if she was playing at, say, a Jingle Ball show with Nick Jonas and Becky G. While Jepsen is an obvious outlier compared to past Pitchfork Music Festivals, she could have easily headlined the festival’s opening night just as well as Beach House. Same goes for Broken Social Scene’s hit-heavy set.

Pitchfork meticulously curates the lineup, but each set is ultimately curated by the individual acts. Any individual artist might choose to cover another artist's song (like Car Seat Headrest expressively did with Bowie’s “Blackstar") or inviting a fellow artist on stage (like Blood Orange did with Jepsen for his highly-hyped but otherwise predictable set; or Porches did with Blood Orange for a massive-sounding set in front of a measly crowd early Sunday; or Jeremih did with Chicago’s beloved Chance the Rapper, last year’s headliner).

These are all examples of artists contextualizing their own bodies of work. (Remember, merit doesn’t help here.) “Look, we’re playing this cool, respected festival, and look, I have another cool, respected artist on stage with me.” Or, “Look, I’m covering this iconic artist because I respect their work and want to be associated with them” (and in turn, further perpetuates the icon’s longevity).

What happens when artists who (theoretically) dream of longevity are on a bill with someone who has already achieved it?

Saturday’s lineup featured Brian Wilson performing the Beach Boys’ 1966 album Pet Sounds front-to-back. By all accounts, this record has reached the epitome of longevity in modern music. 50 years after its release, it’s seen as an essential album and the bedrock for any proper record collection. Pet Sounds has been, over time, deemed a masterpiece; whether something is remotely comparable or not, any and all new music is inherently being compared to it.

How’s that feel, Pitchfork Music Festival 2016 performers that aren’t Brian Wilson?

If you’re Kamasi Washington, Savages, or Sufjan Stevens, it’s gotta feel good, because when there are acts that so obviously stand out in the presence of a legend — a front-to-back performance of a masterpiece (albeit an uninspiring performance) — well, that’s pretty cool.

Savages, who played the same Pitchfork Music Festival stage two years ago, proved that they still deserve to be in the spotlight. Jehnny Beth brought ferocity to the stage (and off the stage, into the crowd) while Gemma Thompson’s guitar, Fay Milton’s drums, and Ayse Hassan’s bass made hearts pound. The band and the crowd were feeding off the blazing energy of the sun.

Washington had a late start to his set (one of the very few delayed starts of the weekend), but easily took the audience from 0 to 60. The West Coast jazz extraordinaire played five songs during the 40-minute set, setting aside plenty of time to let his bandmates flaunt their skills with solos. While Washington led the band with his sax, vocalist Patrice Quinn kept the crowd lively, making it one of the most feel-good sets of the weekend.

And Sufjan. Oh, Sufjan. I regrettably missed his Carrie & Lowell tour when it came through town, so I was eager to watch his headlining performance. I was ready to cry my eyes out and feel solace. “I’ve been touring the world singing about death, loneliness and heartbreak, so I’m going to play some upbeat songs,” Sufjan said, introducing “Too Much.” The band’s coordinated neon outfits themselves brought an uplifting spirit to the show, so much that I couldn’t sneak a single tear. So instead of weeping to the tune of “Should’ve Known Better,” I reflected on Stevens’s rare talent that he has developed in his 16+ years of songwriting.

In his new book, Klosterman makes a sound point: “To matter forever, you need to matter to those who don’t care.” The Pitchfork Music Festival audience obviously cares – about all the acts, not just the highlights.

In 1965, the year before Pet Sounds released, Bob Dylan famously went electric at the Newport Folk Festival. Back then and to this day, Bob Dylan is considered to be a music luminary. Consider other acts on the '65 Newport lineup like Joan Baez or Peter, Paul & Mary: highly praised in their day, but did not see the same longevity as Dylan. They're remembered, but they're an afterthought.

What will be the Pet Sounds of 2016? Moreover, what performers will we remember but wonder, "Hm, what are they up to these days?"

Sufjan Stevens could very well perform Carrie & Lowell front-to-back at the 61st annual Pitchfork Music Festival. Same goes for Savages' Adore Life or Kamasi Washington's The Epic. Or they could all end up in a $3 virtual record bin 50 years from now. These musicians and these albums have merit. They have entered the conversation. But to predict how they fair far off in the future — who and what will achieve longevity — is impossible. We could all be wrong.

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