The song is called “Nostalgia,” and sounds like it. The gentle acoustic guitar. The ambling drum loop coated in rec-room dust. The even gentler flute. The Gundam Wing sample. And above it all, the inimitable voice of Chicago’s own Chance the Rapper, cheerful and mournful, cartoonishly childlike and preternaturally wise, pushing far beyond his years in both directions.

Perhaps you’ve revisited that tune lately, now that Chance’s breakout 2012 mixtape 10 Day—alongside its lusher 2013 follow-up Acid Rap—finally landed on Spotify, etc., in late June, both beloved projects full of childhood reveries, both DatPiff classics old enough now to trigger, in devoted listeners, childhood reveries of their own. On “Nostalgia,” Chance memorializes his path from SpongeBob to The Simpsons to Smart Guy, from birthday-party gift bags to ounces of weed, “From diapers to outfits to castles to Elmos / From Santas to grandmas to Game Boys and cellphones.” It is silly and dainty, an infantilizing Trojan Horse for one gut-punch line: “’Round here we lose best friends like every week / I like to think we playin’ a long game of hide-and-go-seek.”

To repeat, the song is called “Nostalgia.” Chance was 18. Come on. Immediately you see the vast potential. Immediately you see the problem.

The song is called “Paranoia,” and sounds like it. The production upgrade is courtesy of L.A.’s Nosaj Thing, a moody decaying merry-go-round with deep bass hits nearly as percussive as Chance’s braying vowels: “Trapped in the middle of the map / With a little-bitty rock / And a little bit of rap / That, with a literary knack / And a little shitty Mac / And like literally jack.” He feels stuck in Chicago, and per the avalanche of gut-punch lines here and throughout the rest of Acid Rap, the dread of Chicago is forever stuck in him: “They’ll be shooting whether it’s dark or not / I mean, the days is pretty dark a lot / Down here, it’s easier to find a gun than it is to find a fucking parking spot.”

Acid Rap made Chance a critical darling, America’s Mayor, a cuddly ambassador for his city buoyed by the overly simplistic binary between himself and other Chicago rappers like Chief Keef. It also made him, potentially, mainstream rap’s next big superstar; a local hero with intergalactic charisma; a major-label talent beholden, as he was quick to remind us, to no label whatsoever. 10 Day and Acid Rap were not for sale, and neither was he. He was 20, and even at his most haunted and fearful, he radiated enough infectious glee to maybe stay blissfully underage forever.

The song is called “Same Drugs,” and doesn’t sound like it. It is the startlingly beautiful highlight of 2016’s Coloring Book (Chance 3, in the parlance), all churchly piano and piercing melancholy. Chance sings most of it, his falsetto just frail enough to be credible. The topic, once again, is lost innocence, Peter Pan–style: “When did you change? / Wendy, you’ve aged / I thought you’d never grow up / I thought you’d never.” Same with him, though: “Window closed / Wendy got old / I was too late, I was too late / A shadow of what I once was.” In the official video, he duets with a bootleg quasi-Muppet.

Chance won three Grammys in early 2017, including Best New Artist and Best Rap Album, despite Coloring Book’s self-classification as, once again, a mixtape—and a label-free independent mixtape at that, despite it being an Apple Music exclusive for two weeks. Chance had long ago mastered the art of reveling in such contradictions. In 2019, his old stuff sounds disproportionately young and naive while he, himself, seems to be aging in fast-forward.

He is 26, and married, and a father, and, indeed, a rap superstar preparing a July release of what is often described as his “debut album,” an irritating bit of Drake-esque category fraud that underscores how odd and modern his rise to superstardom has been, and how unfixed in time he still seems.

The rerelease of 10 Day and Acid Rap (available on vinyl this fall, along with Coloring Book) has been, thus far, a great success, a nascent legacy reasserted. Acid Rap hit no. 5 on the Billboard 200 (his highest chart position ever), with a revitalized Coloring Book (no. 46) and 10 Day (no. 73) joining it. His catalog thus far lacks the volume and volatility of Drake or Kanye or Young Thug, but there is nonetheless, it turns out, a great deal of public interest in Chance the Rapper’s glorious and not-so-recent past.

His future is a little murkier. Three full years have passed since Coloring Book, an eternity in pop and five eternities stacked atop one another in rap. Chance may have bragged about saving SoundCloud, but a swarm of younger and gnarlier rappers made SoundCloud its own terrifyingly vibrant genre. The four singles he dropped in July 2018, including the Rahm Emanuel–antagonizing “I Might Need Security,” had little impact; Chance has never been a singles artist per se, but he is used to dominating the conversation, no matter what delivery system he deigns to use, even if it’s my second-favorite Kit Kat jingle of all time. (Still undefeated.)

To some, he is an invaluable font of joy and cautious optimism amid the genre’s ever-encroaching gloom; to others, he is OL HAPPY ASS, too superfamous now to maintain the relatability that first propelled him to fame (see his more recent wan single “The Man Who Has Everything”), his philanthropy outpacing his art, his childhood fixations not so much winsomely nostalgic now as uncomfortably regressive. These days he’s most apt to rap about God, about fatherhood, about family, and/or about love, which makes him either a vital antidote to rap hedonism and fatalism, or his generation’s toothless answer to Will Smith. Do we want him to grow up or stay the same age? Does he want to be 5 years old or 35? Nostalgia got him this far, and it’s serving him well even now. But how much further can it take him, and how much further can he take us?

10 Day, named for the high school suspension (for smoking weed, naturally) that gave Chance the free time in which to write it, is a delightful project to revisit even—maybe even especially—in its goofier moments. “Long Time” samples the worldly and warbly indie-rock band Beirut, an awkward echo of Childish Gambino’s own, far less successful genre-hopping mixtape days. There is also a song called “Fuck You Tahm Bout,” a brash bit of ludicrous T.I. cosplay that samples Waka Flocka Flame and finds Ol Happy Ass threatening to “stab you with a screwdriver.” His tough-guy phase was mercifully brief.

Acid Rap is far more memorable for far better reasons, the late-teenage rasp of Chance’s voice a permanent hook, a priceless asset, and a burgeoning religion all its own, whether he’s merely chanting juice juice juice juice! or nah nah nah nah nah nah! or this part right here right now right here this part my shit! Yes, he raps “I miss my diagonal grilled cheeses” on “Acid Rain,” but there’s more pathos to these brushes with nostalgia, a present-tense frustration and uncertainty—“And I still be asking God to show his face”—that is certainly more relatable, among nonbelievers and equally frustrated believers alike, than the gospel-driven exuberance of Coloring Book. God is a central figure on that tape, uncomplicated in his benevolence: “It feels like blessings are falling in my lap,” Chance croons, and you can be happy for him and still feel a chasm opening between the two of you.

“THIS NIGGA LOVE GOD” pic.twitter.com/5bPgyb66Ct — Chance The Rapper Album in July (@chancetherapper) August 15, 2018

Backlash is inevitable with everyone, everywhere, and nobody can get as big as Chance without the vibe turning a little monolithic and corporate, even if no corporation owns his masters. (“Same Drugs,” by the way, showed up in a 2017 HBO documentary about Rolling Stone, soundtracking a montage of the magazine’s turn from scrappy San Francisco clubhouse to straitlaced and cubicle-dense New York City powerhouse.) Part of Chance’s challenge now is the standard pivot from Superstar Rookie to Wily Veteran, an absurd transition to be making before his late 20s, but that’s rap stardom for you.

Nonetheless, it’s the rare rapper who isn’t at his or her best at his or her hungriest. The two best moments in Chance’s catalog to date are not solo tracks: One showcases his power-sharing benevolence, the other his indomitable will to conquer when he wants to. Flush from the triumph of Acid Rap, his next move was to hook up with his old live backing band and release 2015’s Surf, a shaggy and unbothered and casually excellent full-length credited to Donnie Trumpet & the Social Experiment; Donnie Trumpet did, indeed, start out as Chance’s trumpet player. That group-effort record peaks with “Sunday Candy,” the single best track Chance has graced to date, though he’s pointedly not the best part, given the sublime elegance of singer-poet Jamila Woods’s chorus, her awestruck melody like a leaf gently falling to earth. The school-play video is a little retrograde, sure, but it’s a strikingly forward-looking approach to looking backward.

Chance’s other all-universe highlight, of course, is his guest spot on Kanye West’s “Ultralight Beam,” which insured that 2016’s The Life of Pablo peaked on the very first track, and didn’t peak with Kanye at all. Say it with him: “This is my part, nobody else speak.” Actually, don’t say it with him. That song—particularly the Saturday Night Live version, an ultra-rare instance in which Kanye was content to grin from the sideline—was Chance’s coronation, his potential fully realized, his star definitively risen. The raptures of Coloring Book, from the bumptious “No Problems” to the reliably downcast reminisces of “Summer Friends,” were a few months off. But for once his future was as bright, as vibrant, as thrillingly detailed as his past.

It’s not that Chance’s more recent singles have been disappointing, exactly: I am partial to “65th & Ingleside,” a hoarse and rowdy electro-soul ballad dedicated, yes, to Chance’s now-wife, Kirsten Corley, a tender history lesson and a bombastic thank-you letter: “Where’s the return on investment, my first A&R / That shit was played unless you would hit play in the car.” “Work Out,” another of those summer 2018 singles, is a dorky trifle with one very good line: “I know that my girl’s trust is a luxury / I don’t want my next album sounding all Usher-y.” The conundrum, as always, is that contentment, spiritual and otherwise, does not usually make for compelling rap music: Jay-Z never made his marriage to Beyoncé sound more engrossing than he did on 4:44. The challenge, then, is for Chance to exploit his rougher edges, such as they still exist, without blowing up his life.

Speaking of which, if we’re all meant to spend this pre-album interlude indulging in Chance nostalgia, I remain most compelled by one of his few legitimate controversies. In summer 2017, Spin reported that Chance’s management had leaned on MTV News to delete a very thoughtful and only mildly critical piece, written by the critic and reporter David Turner, about a live show on Chance’s Coloring Book tour. Even for those cynical about the backroom machinations of rap stardom, it was a surprising act of oversensitive bullying inconsistent with Chance’s lovable image. And the takedown, once uncovered, had the Streisand Effect of highlighting how perceptive Turner had been about the limits of that image:

The wide-eyed optimism of Coloring Book sounds like a man whose priorities have shifted off himself and towards his child and his new family. This is a necessary pivot in life, but in Chance’s case, the change closed off some of the ways I had into his music. Where before it felt like we were on a similar path, wrestling with taking friendships into adulthood and the role that parents play in one’s life as an adult, suddenly Chance’s accelerated life priorities had created a noticeable gap between artist and listener. This divergence became even clearer with his childhood-themed stage production, evoking a nostalgia for life’s earlier days that I’m fine allowing to remain in the past.

Chance did “Same Drugs” as a puppet duet onstage, too, and Turner likewise astutely described the unease that staging creates:

The song catches Chance reflecting back on the various ways that friends can grow apart as they grow older. For all his Christian themes, Chance still isn’t a preacher in cadence or tone; the performance of “Same Drugs” didn’t disdain or shame drug use, nor did it talk down to the thousands of festivalgoers who might be going through similar life changes. Truthfully, it felt like the song’s message wasn’t meant for us in the audience at all. The giant puppets and over-elaborate stage production all seemed like Chance the Father trying to impart life wisdom to a child rather than emotionally connect to his peers in the crowd.

The short version is that Chance is a husband, and a father, and a devout believer who shares his relationship with God more explicitly than most of his superstar-rapper brethren, and the distance this creates for many 10 Day and Acid Rap fans will only exacerbate the usual backlash, and complicate his imminent (yeah, fine, sure) debut album in ways that may actually improve it. He is far from washed; he is far from Willlennium. I am very excited for Chance 4, and given the moribund rap (and pop!) landscape of summer 2019, so, in all likelihood, are you. But his narrative needed a villain; in the absence of a worthy candidate, for those who’ve long tired of his relentless happy-assedness, Chance himself will have to do. Let him grow up. But feel free to heckle him a little while he struggles, like all of us, to do so.