On February 23, 1999, The Roots released their fourth album, Things Fall Apart, a pivotal entry into their discography.

The album title was inspired by Chinua Achebe’s classic book of the same name, which was inspired by a poem by W. B. Yeats. Created during the beginning of The Soulquarian's genius run, which included landmark albums from Common (Like Water for Chocolate), Erykah Badu (Mama's Gun), and D'Angelo (Voodoo), Things Fall Apart elevated The Roots to another level, becoming their first album to go gold.

“We were kind of near the 400,000 [sales] mark, and we felt that ‘What They Do’ would have finally like brought us to platinum,” Questlove said in a 2019 interview. “It didn’t happen, even though the video was loved. We decided that this next album was going to be a do-or-die moment.”

The album was led by the single, "You Got Me," co-written by Jill Scott, sung by Erykah Badu and featuring Eve, which still stands as one of the greatest rap love songs of all time, and won a Grammy.

"The Next Movement" featuring Philly soul group Jazzyfatnastees, "The Spark" and "Dynamite!" are among the standouts on the album, which is anchored by thoughtful lyrics and a liquid approach to production that was both malleable and grounded in jazz and Hip-Hop roots.

Considered The Roots' major breakout album, Things Fall Apart remains a star in their lengthy discography.