Singer-songwriter Elliott Smith released XO, his fourth album and major label debut, on August 25, 1998. The album marked a shift in the sound of Smith's music towards grander gestures and lusher production. During its recording, Smith's profile jumped from esteemed indie songwriter to Oscar nominee, for a song featured in 1997's "Good Will Hunting." But XO also turned out to be the musician's second-to-last LP, released five years before his death at the age of just 34. Jayson Greene, contributing editor at Pitchfork, joins us to discuss the legacy of XO and Elliott Smith's career.

This segment is guest-hosted by Kerry Nolan.