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Elliott Smith's XO stands as a bittersweet monument to what might have been—a gorgeous, haunting collection that captures an artist at the peak of his powers, even as personal demons lurked in the shadows. Released in 1998, this album marked Smith's major label debut and his most polished work, yet it pulses with the same raw vulnerability that made him indie rock's most heartbreaking troubadour.

The path to XO began in the aftermath of Smith's previous album, Either/Or, which had garnered critical acclaim but modest sales. Everything changed when director Gus Van Sant selected Smith's "Miss Misery" for the Good Will Hunting soundtrack, catapulting the shy, whisper-singing songwriter from Portland coffee shops to the Academy Awards stage. Suddenly, major labels came calling, and Smith found himself in the surreal position of performing his delicate ballad at the Oscars ceremony in 1998, looking visibly uncomfortable in his white suit as he competed against Celine Dion's "My Heart Will Go On."

This unexpected spotlight led to his signing with DreamWorks Records, where he was given a substantially larger budget to craft XO. Working primarily at Sunset Sound and Capitol Studios in Los Angeles, Smith embraced a fuller, more orchestrated sound while maintaining the intimate songwriting that had made him a critical darling. The result is an album that bridges the gap between his lo-fi indie origins and mainstream accessibility without sacrificing an ounce of emotional authenticity.

Musically, XO represents Smith at his most ambitious. While his earlier work relied heavily on double-tracked vocals and sparse instrumentation, here he incorporates lush string arrangements, subtle brass sections, and more prominent drums. The production, handled by Smith himself along with Rob Schnapf and Tom Rothrock, creates a warm, enveloping sound that feels like being wrapped in a melancholy embrace. It's baroque pop meets indie folk, with Beatles-esque harmonies floating over chord progressions that seem to spiral inward on themselves.

The album opens with "Sweet Adeline," a deceptively gentle number that showcases Smith's gift for melody while hinting at darker undercurrents. The real knockout punch comes with "Tomorrow Tomorrow," a swirling, orchestrated piece that builds from a simple piano figure into something genuinely epic. Smith's voice, always his secret weapon, floats above the arrangement like smoke, delivering lines about disappointment and longing with devastating precision.

"Baby Britain" stands as perhaps the album's masterpiece—a perfect encapsulation of Smith's ability to wrap profound sadness in irresistible hooks. The song's jaunty rhythm and bright instrumentation provide stark contrast to lyrics about emotional numbness and disconnection. It's this tension between surface beauty and underlying pain that makes XO so compelling. "Pitseleh" offers another highlight, with its hypnotic guitar figure and Smith's most tender vocal performance, creating an atmosphere of intimate confession.

The album's emotional centerpiece might be "Independence Day," where Smith's fragile voice delivers devastating observations about family dysfunction over a backdrop that's both lush and lonely. Even "Bled White," despite its ominous title, transforms personal anguish into something approaching transcendence through sheer melodic beauty.

XO's legacy has only grown in the decades since its release. Following Smith's tragic death in 2003, the album has been reassessed as not just his commercial peak but perhaps his artistic one as well. It influenced countless indie artists who learned from Smith's example that vulnerability could be a strength, that whispered confessions could be more powerful than shouted anthems. Bands like Death Cab for Cutie, The National, and Phoebe Bridgers all owe debts to the template Smith perfected here.

The album stands as proof that major label resources don't have to corrupt artistic vision—in Smith's hands, bigger budgets simply meant more colors on his palette. XO captures that rare moment when an artist's personal vision aligns perfectly with broader accessibility, creating something that speaks to both critics and casual listeners.

Nearly three decades later, XO remains a masterclass in melancholy, a beautiful and devastating document of one man's struggle with depression, addiction, and fame. It's an album that rewards both casual listening and deep study, revealing new layers of meaning with each encounter. In Smith's catalog, XO represents the sound of an artist fully realizing his potential while battling the forces that would ultimately consume him—making it all the more precious and heartbreaking.