1. Air, Moon Safari
What was this? The super-chill debut album by a couple of suave yet introverted French dudes. You might've made out with someone while listening to this.
What was the popular song on it? "Sexy Boy" was their radio/MTV hit, but "La Femme d'Argent" was the boudoir jam.
2. Ani DiFranco, Living in Clip
What was this? Ani DiFranco's first live album was everywhere, in part because it was the easiest way to jump into her body of work. At the time this came out, she already had seven studio albums.
What was the hit? You're probably thinking of "32 Flavors," the Ani song that turned up on the most mixtapes back then.
3. Black Star, Mos Def & Talib Kweli Are Black Star
What was this? The indie rap album of '98, and the record that put Mos Def and Talib Kweli on the map.
What was the hit? "Definition," which is one of those songs that somehow gets better if you put it on repeat for a half hour.
4. Dr. Octagon, Dr. Octagonecologyst
What was this? Hip-hop veteran Kool Keith reinvented himself on this deeply weird, grimy, and often pornographic record under the name Dr. Octagon. When it came out it felt like it was from the future, so it makes sense that it'd hold up so well today.
5. Massive Attack, Mezzanine
What was this? The third album by the kings of trip-hop. Remember back when Nerve personals were a thing and this was the song virtually everyone mentioned this as the record to put on while having sex? Yup.
What was the hit? "Teardrop," which is better known today as the theme song from House.
6. Belle & Sebastian, If You're Feeling Sinister
What was this? The breakthrough album by the greatest twee band of all time. This is one of those records that didn't really chart on the time, but filled out thousands of mixtapes made in the late '90s.
7. Wilco, Summerteeth
What was this? Wilco's last album as an underdog "alt-country" band before crossing over a few laters with Yankee Hotel Foxtrot. This is a lot of people's favorite Wilco record.
8. Spiritualized, Ladies and Gentlemen, We Are Floating in Space
What was this again? The biggest and boldest record by Jason Pierce's space rock orchestra. One of the best albums about being a heroin junkie ever, and there's some major competition on that front.
9. Radiohead, OK Computer
What was this? Oh come on, you know what OK Computer is. It hasn't gone away. It's one of the most acclaimed rock albums of all time. You probably know at least one person for whom this record was basically their religion circa 1998. It might have been you.
10. Björk, Homogenic
What was this? Björk's third solo record, and the album on which she ascended to art-pop deity status.
11. Wu-Tang Clan, Wu-Tang Forever
What was this? The double-disc sequel to the Wu-Tang Clan's classic debut, Enter the Wu-Tang (36 Chambers). No, it's not as good as the first one. But almost nothing in life is. There's a few duds, but it's mostly amazing. Seriously, go back to this if you haven't in a while.
12. Erykah Badu, Baduizm
What was this? The debut by one of the most original voices in modern R&B. This was the record that really kicked the "neo-soul" movement into high gear.
13. Pavement, Brighten the Corners
What was this? The fourth album by the greatest indie rock band of all time. This is their most refined and chill record, and the one where they actually get a bit jam band-ish.
14. Beastie Boys, Hello Nasty
What is this? It's a Beastie Boys album, obviously! It's the record that came after Ill Communication, and it has some alt-rock–type songs tossed in among the more traditional rap tracks.
What's on this one again? The big hit everyone knows is "Intergalactic," and "Body Movin'" was popular too. Also, this is a great time to mention that "Unite" is one of the Beasties' all-time best deep cuts.
15. Portishead, Portishead
What was this? The second album by the moodiest, sexiest trip-hop band ever. Some elements on this record feel very late '90s — the DJ scratching, for example — but these ballads really hold up.
16. Yo La Tengo, I Can Hear the Heart Beating as One
What was this? The culmination of a decade of hard work, basically. This is the record where Yo La Tengo broke through and found their audience. It's still their most popular record, and for good reason — it's eclectic and consistently great, and features a lot of their best songs.
17. Various Artists, Rawkus Presents: Soundbombing II
What was this? The second in a series of compilations featuring artists from the Rawkus roster. Every single dude with a passing interest in backpacker hip-hop owned a copy of this.
What was the hit? You know, the whole aesthetic of this is anti-"hit." But Common's "One-Nine-Nine-Nine" was a single.
18. Elliott Smith, XO
What was this? The most popular album by the arguably saddest songwriter of the '90s. This is the record where he made the jump from lo-fi to a more polished style that brought out the Beatles-ness in his tunes.
19. Stereolab, Dots and Loops
What was this? Stereolab were a French-British band who specialized in groove-based indie music built from elements of art rock, punk, and '60s kitsch. Dots and Loops wasn't their best record that would be the album that immediately preceded it, Emperor Tomato Ketchup — but it's their most electronic, and the one best suited to being played while you do homework in a cafe.
What was the hit? The single was "Miss Modular," and it's delightful.
20. Phish, A Live One
What was this? The first official live album by the band who carried the torch for jam band culture after Jerry Garcia died. This was a lot of people's entry point for the band, which makes sense since they're known mostly for their live shows.
What was the hit? Oh, you know, the long jammy one.
21. Cat Power, Moon Pix
What was this? Oh, just one of the prettiest and saddest things you'll ever hear in your life. Chan Marshall had been recording as Cat Power for a while at this point, but this is the record that made her an indie star.
22. Cornershop, When I Was Born for the 7th Time
What was this? The breakthrough album by the genre-bending Indian-British band. This is a truly eclectic and joyful album; it's really too bad no one really talks about it anymore. It definitely holds up.
23. Various Artists, Buena Vista Social Club
What was this? The soundtrack to a documentary about Cuban musicians who were not known outside of Cuba. The record is all new recordings compiled and produced by Juan de Marcos González and Ry Cooder. It was a surprise hit, and ended up being one of those CDs that always could be found in a someone's "eclectic" record collection.
What were the hits? "Chan Chan" was sorta the hit, but you've definitely heard all of these songs played a restaurant at some point.
24. Sleater-Kinney, Dig Me Out
What was this? The breakthrough album by one of the great rock bands of the '90s. You might know Carrie Brownstein today as "that woman from Portlandia."
25. Tricky, Pre-Millennium Tension
What was this? The second proper album by one of the most fascinating and distinct producers of the '90s. This record is all lust and paranoia, and the best songs make the most of the odd sexual chemistry between Tricky and his lover/muse, Martina Topley-Bird.
26. Built to Spill, Keep It Like a Secret
What was this? The most epic album by an indie rock band who specialize in huge, cinematic anthems. It's kinda like the halfway point between Billy Corgan and Neil Young.
27. The Magnetic Fields, 69 Love Songs
What was this? It's exactly what it says it is – 69 love songs penned by The Magnetic Fields' Stephin Merritt. It's very consistent, and everyone has their own unique set of favorites.