5 Quintessential Albums That Turn 25 in 2025

As 1999 wound to a close, the approaching millennium brought much anxiety.

But a few artists turned their angst and fear into enduring masterpieces. Twenty-five years later, these albums are no less remarkable. Uniquely, each release documents the threshold of leaving behind the ’90s and what came next. Though the music is varied, each offers a glimpse of life and culture where it was and where it was headed.  

This collection celebrates five quintessential albums released 25 years ago.

Kid A by Radiohead

With OK Computer, Radiohead had redefined what a rock band could sound like. Then arrived Kid A, and the Oxfordshire, England, group abandoned rock music entirely. Thom Yorke wasn’t interested in guitars, or choruses, or even melody. He chose, instead, to deconstruct his band. Kid A is interesting because it’s the sound of a brain recalculating. Imagine Jonny Greenwood’s patch bay, plugging and unplugging the synapses, trying to make sense of glitching beats and avant-garde jazz. Yorke’s lyrics are mere fragments, thought puzzles. They sound like nonsense until they don’t. Radiohead destroyed itself. This is the sound of that process. It’s not the weird noises that sound alien. It’s the resulting perfect album.

All That You Can’t Leave Behind by U2

After years of experimenting with dance and electronic music, U2 reunited with producers Daniel Lanois and Brian Eno. Though many panned Pop, some (ahem) defended it. Still, the old U2 returned. “Beautiful Day” returns to the ecstasy of Bono’s loftiest chants. “Stuck In a Moment You Can’t Get Out Of,” “Elevation,” “Walk On,” and “Kite” fill out the first half like it’s a greatest hits record. Then there’s “In a Little While.” Utterly gorgeous. The story goes that it’s the last song Joey Ramone heard before he died. Ramone’s farewell transformed a drunken ballad into a punk rock hymn. U2 didn’t just recycle a familiar sound. They corralled high ambitions into concise, well-crafted rock songs.

The Marshall Mathers LP by Eminem

Eminem’s colossal third album changed rap music, but it also changed pop culture. Listening to “The Real Slim Shady” makes time traveling seem possible. The tracks are like little tornadoes of memes using rapid-fire wit to reflect the messiness of life back onto listeners. “Stan” uses a sample of Dido’s “Thank You” to detail a fictional account of tabloid-frenzied fan worship. To prove the song’s ubiquitousness, if you check your dictionary, you’ll find the word “stan” in it. It’s a silly exercise to say so-and-so is the “greatest ever.” But a better rapper than Eminem does not exist.

Voodoo by D’Angelo

Five years lapsed between D’Angelo’s debut Brown Sugar and its follow-up Voodoo. On it, he employs groove like a religion, mixing old-soul funk, jazz, gospel, and rock. Recorded at Electric Lady Studios, Voodoo reacted against ultra-slick ’90s R&B with the dirt and warmth of 2-inch tape and vintage gear. Questlove said D’Angelo instructed him to play like he’d “drank some moonshine behind a chuckwagon.” The audible result of this drunk-drumming style appears on the hit “Untitled (How Does It Feel).” You see the fingerprints of legends like Prince, Stevie Wonder, and J Dilla, but D’Angelo used their guiding hands to make his own work of genius.

Figure 8 by Elliott Smith

Autumn de Wilde’s famous Figure 8 photograph has inspired many pilgrimages to visit the mural on Sunset Boulevard. Elliott Smith wrestled with the image of perfection on his final studio album. “I liked the idea of a self-contained, endless pursuit of perfection. But I have a problem with perfection. I don’t think perfection is very artful,” Smith told the Boston Herald in 2000. This balancing act followed Smith for his entire career. Folk singer and punk rocker. Underground gem and Oscar nominee. Smith is like a genre to himself—a brilliant and beautiful musician, gone too soon.

Photo by Frans Schellekens/Redferns