Whoa, we’ve hit the top 20! I’ve been writing this column since 2011, because like a good Gen X-er, I didn’t care that much about following through. Alas, here we are. Five more ’90s classics in ya ear. (You can check out the whole list here.)

20. Beastie Boys – Check Your Head (1992)

That cover image you’re looking at right now, with the Beastie Boys sitting on a curb next to their instrument cases? It wasn’t a joke. Even though Mike D, MCA and Ad-Rock had just reinvented themselves, against all odds, on the triumphant samplepalooza Paul’s Boutique, they took an even bigger risk on the follow-up – ditching their old producers and proven formulas so they could play their own loose concoction of funk, rap and hardcore punk. Like the Monkees, novelty-act status had masked the fact that the Beastie Boys had legitimate musical chops. Check Your Head is stuffed with monumental riffs and meditative instrumentals, lovingly sequenced into 20 tracks that resist the shuffle button. The rapping reflects this anything-goes, jam-session mentality, summed up by Mike D on track one: “All I ever really wanna do is get nice / Get loose and goof a little slice of life.” Only six years after “Brass Monkey” squawked its way onto the charts, this deeply musical, effortlessly electrifying LP entered the world. It was irrefutable proof of one of popular music’s greatest evolutions.

19. Nas – Illmatic (1994)

There’s a moment, before Nasir Jones raps a word of his debut album, that underlines how incredibly fresh his artistry was. As the ominous, subway-rattling bass line of “NY State of Mind” ramps up underneath, the 20-year-old MC confesses into the mic, “I don’t know how to start this.” And then, even though the ink is still drying, he jumps in, telling stories about life in New York’s Queensbridge projects that are so detailed, you can hear the dice hitting the walls: “On the corner bettin’ Grants with the cee-lo champs / Laughin’ at base-heads tryin to sell some broken amps.” Illmatic is a masterpiece of scene-setting, a clinic of internal rhymes, and an emotional watershed from a composition-book-scrawling kid who grew up surrounded by violence and nourished by poetry. And the beats – crafted by top producers of the ’90s – dramatically soundtrack these vivid scenes, from the clave-clacking quiet-storm R&B of “Life’s a Bitch” to the mournful organ loop of “Memory Lane.” He may have had no clue how to begin, but once Nas took that leap, it would be 38 minutes before he touched the ground.

18. Lucinda Williams – Car Wheels on a Gravel Road (1998)

Lucinda Williams wanted her fourth album to sound a particular way. Warmer, punchier, more like the Pretenders or Steve Earle – “His vocals were more outfront, and it was a bigger sound,” she said about the latter. And thankfully, she stuck to her guns, through six years of label flameouts and disagreements with stubborn male producers (Earle included). Because Car Wheels on a Gravel Road sounds big in the most authentic possible way, a deeply rooted Louisiana oak that we can lean up against for an afternoon. It opens with “Right In Time,” an achingly physical love song that pairs visceral yearning (“Think about you and that long ride / I bite my nails, I get weak inside”) with a chiming guitar riff that’s as fulfilling as the sound of your lover pulling into the driveway. As Williams goes on to explore the nooks and crannies of Southern music, from jukebox country to jailbird folk and dobro-happy roots-rock, the connective tissue is her voice – defiantly front and center, singing about wandering spirits seeking meaning, making it seem like the journey itself could be enough.

17. The Roots – Things Fall Apart (1999)

With the millennium coming to an end, the Clinton crime bill wreaking havoc on black communities, and an extended era of anti-Muslim fear-mongering right around the corner, The Roots released an album called Things Fall Apart. It was, quite ironically, the moment where everything came together for them. There’s a feeling of unrest throughout, an understanding that now it’s time to spark shit. Beats fade away in the middle of verses, the rappers left alone to soldier on. Its lead single, a love song about trust, prominently features the line “sometimes relationships get ill.” Its bookends are an argument between musicians from Mo’ Better Blues and a spoken word screed about the cycle of abuse. But even with the pull of these serious undercurrents, Things Fall Apart is a delight to listen to, a telepathic group at its peak, lovingly laid to tape. The crisp crack of Questlove’s snare; Kamal Gray’s nourishing Fender Rhodes vamps; Black Thought’s sweat-on-the-mic intensity – it gels in that next-level Revolver way. Resulting in a record that makes you feel grateful for its artistry, and wary of what’s to come.

16. Smog – Knock Knock (1999)

“Let’s go to the country / just you and me,” goes the opening lines of singer/songwriter Bill Callahan’s seventh LP. But that invitation wasn’t as casual as it sounded. Knock Knock found Callahan expanding his palette, both lyrically and instrumentally, the obscure lo-fi vision of his early albums making way for richly rendered, naturalistic tone-poems about empathetic prison guards, bone-chilling childhood traumas, and restorative balms of affection. “I lay back in the tall grass / And let the ants cover me,” he sings in his rumbling basso, describing a moment of psychological healing like Leonard Cohen on a Thoreau kick. The music is equally exploratory, using bouncing cellos and children’s choirs to buoy Callahan’s lush, searching guitar. It’s a formula he’d take to even more panoramic heights later on in his career, a smirking cowboy wading through amber waves of pain, coming out the other side humbled and smitten. Making Knock Knock even more meaningful in context. This isn’t just some invitation to a three-day weekend on the lake. It’s an artist taking the first steps into the underbrush of his soul.