The 30 Best Albums of 1999

Music Lists Best Albums
The 30 Best Albums of 1999

As the 1990s came to a close, the music industry was in a strange place. Portable MP3 players were just hitting the market, but major labels had no idea how to respond. A decade of trying to find the next grunge hit or nu-metal clone left rock radio with bands like Creed, Godsmack and Korn dominating the airwaves. Pop radio was an endless barrage of the Backstreet Boys, Christina Aguilera and Britney Spears. There were plenty of bright spots both above and below the surface—in hip hop, college rock, alt-country and punk, but they were often overshadowed by forgettable music you couldn’t escape. Just a month before the year started, frustrated with the state of the music industry, some friends and I started a music company called Paste to highlight some of our favorite overlooked bands. Looking back, it was an amazing time to jump into the industry as everything was about to change. And as this list illustrates, there were a whole lot of musical acts to be excited about. These 30 albums, voted on by Paste music editors and writers, are the albums we remember best, those that would help shape the music of the new millennium.

Here are the 30 best albums of 1999:

boredoms-vision.jpg30. Boredoms: Vision Creation Newsun
Ever since forming 30 years ago, the avant-garde group Boredoms have been pushing the boundaries of genre, composition and music itself under the leadership of auteur and certified oddball Yamatsuka Eye. While their punky, noisy releases such as Pop Tatari are well regarded in their own right, the supersonic ascent of Vision Creation Newsun truly blows minds. Boredoms blend krautrock, psychedelic rock, electronic and whatever genre Yamatsuka may be listening at the time into one freewheeling epic piece that transitions seamlessly from track to track, creating a masterpiece of noisy electronics and tribal drumming. Prepare for an album that establishes itself as mind-bending journey within the first minute and doesn’t let up from there. —Robert Ham

handsome-boy.jpg29. Handsome Boy Modeling School: So… How’s Your Girl?
When it comes to producing concept albums, Dan The Automator and Prince Paul are the gold standard. On their first collaboration, the Handsome Boy record borrows snippets from the short-lived HBO series Get A Life starring Chris Elliott to tell the story of school that helps men become…well…Handsome. Del Tha Funkee Homosapien’s “Magnetizing” and “Once Again” featuring Brand Nubian are the winners here. But the courtroom jargon themed “The Truth” with J-Live’s flows and Roisín Murphy’s (of Moloko) smooth vocals, lingers on the listener’s mind long after the album has finished. —Adrian Spinelli

missy-real.jpg28. Missy Elliott: Da Real World
The freaky promo for Da Real World’s first single saw Missy spray paint her head black and don a catsuit, spiked G-string and skull cap combo designed by none other than Marilyn Manson’s tailor. It was a bold and uncompromising look that perfectly matched the no-holds-barred nature of the track itself. Yet, with Timbaland’s minimalistic production—essentially just a hypnotic shuffling beat and some grimy Missy’s words take center stage. “She’s a Bitch” proved how hell hath no fury like an R&B visionary scorned. And if the Da Brat collaboration “Sock It 2 Me,” had hinted that she possessed a melodic vocal style every bit as impressive as her lyrical flow, “Beep Me 911” confirmed it. Indeed, the sweetly-sung tones of guest stars 702 are always welcome, but Missy could quite easily have carried this song entirely on her own. Far from the booty call its title suggests, Da Real World’s second single instead is a break-up anthem in which Missy simply wants an explanation from the cheater for whom she “gave up clubs and parties.” Timbaland’s trademark vocal tics and clickety-click beats are still present, but with Elliott in uncharacteristically vulnerable mode, “Beep Me 911” undoubtedly stands out from the crowd. “Why you all n my grill. Can you pay my bills?” On paper, the second single from Da Real World could have been mistaken for any of the good-for-nothing smackdowns that emerged in the wake of TLC’s “No Scrubs.” While “All n My Grill’s” theme may have been familiar, its sound was anything but. There’s the eerie strings that appear to have wandered in from a classic Hitchcock movie, some glorious diva-ish ad-libs from Missy discovery Nicole Wray (who has since performed as Lady and as Lady Wray at the Paste Studio earlier this year). And on the European version, the masterful substitution of Outkast’s Big Boi for Frenchman MC Solaar, whose languid delivery and tongue-twisting wordplay elevated the track to new stylish heights. —Jon O’Brien

old-97s-fight.jpg27. Old 97’s: Fight Songs
While Old 97’s didn’t create the alt-country moniker, they certainly helped popularize the genre. Rhett Miller’s songwriting and vocals fill Fight Songs with such a loneliness and desperation, you can almost hear his heart breaking under the slide guitars. The album is indeed packed with “fight songs,” whether that means fighting for love on “Lonely Holiday,” fighting with rival Ryan Adams on “Crash On The Barrelhead” or fighting to get their cat back on “Murder (Or A Heart Attack),” Old 97’s created a roots record as fun as it is brilliant. —Ross Bonaime

xtc-apple.jpg26. XTC: Apple Venus Vol. One
Nineteen ninety-nine was a year of renewal for XTC. They had snipped the shackles of their previous contract with Virgin Records and, after seven long years, were free to record new music under their own name. Is it any wonder then that group’s penultimate album was, primarily, an acoustic guitar-driven ode to the natural world, the restorative qualities of love and a gentle sigh at the lingering end of one’s days. The arrangements were lush and warm, like sinking into a sun-soaked lawn, and Andy Partridge and Colin Moulding’s lyrics were dripping with detail and sly wit. The tonic nature of Apple Venus also included a bit of deck-clearing, with Partridge excoriating his ex-wife in the nasty “Your Dictionary” (“F-U-C-K/Is that how you spell friend/in your dictionary”). That it fit perfectly within the otherwise starry-eyed tone of the album is a testament to their skills as arrangers and performers. It’s a bee sting on an otherwise idyllic afternoon. —Robert Ham

guster-lost.jpg25. Guster: Lost and Gone Forever
Charting the evolution between Lost and Gone Forever and Guster’s previous release, 1997’s Goldfly, is like comparing a snapshot and a finely detailed painting: They were still the same hook-happy pop band with a hand percussionist for a drummer, but with producer Steve Lillywhite at the helm, they used the studio as an instrument, coloring their new songs with layers upon layers of sonic texture. Sadly, their efforts weren’t rewarded on the charts, where singles like “Barrel of a Gun” and “Fa Fa” failed to gain much traction, but the album pointed the way toward broader horizons for the band—and it contains a number of tracks that remain highlights of their catalog, including “What You Wish For,” “Either Way,” “Center of Attention” and “Happier.”—Jeff Giles

olivia-black.jpg24. Olivia Tremor Control: Black Foliage
With the climactic CD Black Foliage, the Olivia Tremor Control solidified themselves as heirs to Pink Floyd’s legacy. The most psychedelic member of Athens, Ga.’s Elephant Six Collective took a foundational bass line and sped it up, slowed it down and otherwise used it as the basis for a large chunk of the project’s songs. The effect is realistically surreal: certain songs sound unaccountably familiar. Dali got it wrong. Surrealism isn’t about melting clocks and barren Andalusian landscapes. It’s about something that seems almost completely normal that is actually almost completely not. The Olivia Tremor Control assume the Pink Floyd throne largely due to their compulsive attention to lost detail. They killed themselves orchestrating and arranging all this multi-instrumental brilliance—and then most of it got lost in the lo-fi swirl of their homemade production. Strangely, the residual intent of the band’s compulsive arrangements still come through. How such structured orchestration arises from the flatlands of eight-track production, I don’t know, but after infinite listenings, the Olivia Tremor Control loom in my mind as large as Syd Barrett, Brian Wilson, Frank Zappa or any other canonized musician you care to name. Had Barrett stayed with Pink Floyd instead of flipping out, Black Foliage is the album Pink Floyd might have cut. —Curt Cloninger

ben-folds-reinhold.jpg23. Ben Folds Five: The Unauthorized Biography of Reinhold Messner
Sure, The Unauthorized Biography of Reinhold Messner is a more melancholic affair than either of Ben Folds Five’s previous two albums, save for two songs: “Army” (with perhaps the best opening lyric of all time) and “Your Redneck Past.” It’s the soundtrack of a band unraveling right in front of us. But it’s also Ben Folds’ finest moment as a songwriter. From the gorgeous piano build on album opener “Narcolepsy” through the Burt Bacharach-esque throwback ballad “Lullabye,” …Reinhold Messner, named after the name on drummer Darren Jessee’s fake ID as a teenager, is a gorgeous and deep listen, one that showcases Folds’ biggest strengths as a songwriter—his ability to write from different perspectives, all of which have quite a bit of autobiographical elements to them. —Steven Edelstone

mos-def-black.jpg22. Mos Def: Black On Both Sides
One year after Black Star raised the bar with their debut album, one-half of that vaunted duo took hip hop to a whole new level of consciousness and window rattling thrills with his solo debut. With production help from icons like DJ Premier and Psycho Les of the Beatnuts and choice guest spots from Q-Tip and Busta Rhymes, Mos Def’s first album is a defining document of the boom-bap era that was the logical evolutionary step beyond Midnight Marauders and Illmatic. And it was the perfect companion piece to Lauryn Hill’s solo effort from the previous year as Mos Def wound in touches of jazz, dancehall and languid soul. The cool, boastful shit was there, but it had to fight for room alongside musical history lessons (“Hip Hop,” “Rock N Roll”), tear-stained diary entries (“Umi Says”) and unbridled lust (“Ms. Fat Booty”). A full meal that left you hungry for more. — Robert Ham

vol-audible-sigh.jpg21. Vigilantes of Love: Audible Sigh
Singer/songwriter Bill Mallonee changed lineups to his Athens, Ga., outfit like some frontmen change hairstyles, and with the personnel moves came a variety of styles from alt-folk to indie rock and even Americanized Brit-pop. But one of the band’s best album’s was a straight-up alt-country gem. Audible Sigh benefitted from Kenny Hutson’s versatility on mandolin, guitar, pedal steel and dobro, production from Buddy Miller and backing vocals from Emmylou Harris on standout track “Resplendent.” It’s Mallonee’s vivid songwriting that elevates the album to “overlooked classic” status, though. Audible Sigh trades in Dustbowl imagery more than most of his catalog, but he can’t stay completely away from the personal demons he’s spent a career turning into confessional songs, like on “She Walks on Roses”: “They say that pride, well it’s the chief of sins/Well I know all of his deputies, I’m well acquainted with them.” Song titles like “Hard Luck and Heart Attack” and “Black Cloud O’er Me” fit well on the twangiest album of his impressive catalog. —Josh Jackson

sleater-hot-rock.jpg20. Sleater-Kinney: The Hot Rock
It was always going to be hard to follow the classic punk jams of Dig Me Out, but Sleater-Kinney managed a worthy follow-up, venturing into darker territory on The Hot Rock. They still have a fire in their belly, but lyrically and melodically, The Hot Rock is more brooding than its predecessors. The title track is a perfect example of the back and forth lead vocals that make Sleater-Kinney so tantalizing—Corin Tucker’s fluttering, almost operatic vocals matched with Carrie Brownstein’s cool, airy speak-sing is a juxtaposition that pleases without fail—but its melodies sound more wistful this time around. “God is a Number” features lyrics about technological despair and spiky riffs while “Don’t Talk Like” explores naivete and blends noise rock with post-punk—their guitars are glittery and sharp, other times shadowy and dissonant. “The Size of Our Love” is one of the most tender songs they’ve ever released, as Brownstein sings about loving someone on the brink of death, but it also has a murky edge with distorted guitar cries. Corin Tucker sings at the beginning of the album, “If you want me, it’s changing,” and Sleater-Kinney changed gracefully by retreating inward while preserving their rowdy allure. —Lizzie Manno

rsz_bonnie_billy.jpg19. Bonnie “Prince” Billy: I See a Darkness
If Johnny Cash covered one of your songs on his final albums, it automatically meant it embodied some sort of country spirit however musically disguised. Cash, of course, interpreted the title track from this 1999 record the following year on American III: Solitary Man. I See a Darkness is dark, yes. It is gothic without being goth. Yet, its confessional cries and distant, discordant layering (especially on tracks like “Nomadic Revery (All Around)”) are also subversive in a way that honors the subgenre. —Hilary Saunders

rsz_julie_miller.jpg18. Julie Miller: Broken Things
A little girl voice that held ages, “Broken Things” offered redemption as well as deep love for those damaged by life. For Julie Miller, whose second album for Hightone following a Christian career, there was always salvation peeking through the cracks of her songs. Beyond the divine, there was the charismatic “I Need You,” the Appalachian dirge “Orphan Train” and the percussively minor-keyed creeper “Strange Lover,” an homage to – of all things — cocaine. Emmylou Harris would record the shimmering “All My Tears” and Lee Ann Womack would embrace “Orphan Train” and “I Know Why The River Runs,” further broadening Miller’s reach. But the songwriter with a dexterous voice that does many things – howl, coo, caress and throttle – remains her own best interpreter. “I Still Cry,” a straightforward elegy, suggests the way some people linger in unlikely ways long after they’re gone with the sorrow profoundly transparent in her tone, bringing both naked vulnerability and intuitive playing that exemplifies the best of Americana. —Holly Gleason

moby-play.jpg17. Moby: Play
Richard Melville Hall became electronica’s unlikely ambassador on Play, an achingly beautiful, eclectic showcase of lush synths and drum loops cradling a collection of relic blues loops from Warner Bros.’ basement. Even if it was a bipolar train wreck on paper, Moby’s obsessive production and underrated chops produced a surreal soundscape where wah-pedal funk hymns like “Bodyrock” coexist with the existential melancholy of instrumentals “Everloving” and “My Weakness.” With all 18 tracks licensed for film and TV, Play was the ubiquitous soundtrack of 1999. —Sean Edgar

pavement-terror.jpg16. Pavement: Terror Twilight
Lead singer Stephen Malkmus doesn’t like this record, and he’s gone on record multiple times since its release 20 years ago to critique it. In an interview with Pitchfork in 2015, he called it the “accidental child of the Pavement catalog.” Two years later, he said, “With that much money you should be able to make something good. We made some things that weren’t as good as they could’ve been.” But here’s the thing: We all know it’s not Pavement’s greatest record, but that still doesn’t mean it isn’t great in its own right. “Spit on a Stranger” is one of their best-written songs, while “Major Leagues” acts as a fuller-sounding “Range Life.” Even a slightly-underwhelming Pavement record is still better than almost anything else. Terror Twilight wasn’t meant to be the legendary band’s swan song, but it can definitely be appreciated as such. —Steven Edelstone

blur.jpg15. Blur: 13
The jury’s still out on which Blur LP is their finest, but they make a strong case on 13. Their 1999 sixth studio album was written in the aftermath of Damon Albarn’s breakup with Elastica lead singer Justine Frischmann. It opens with the Primal Scream-esque “Tender” with its gospel choir vocals and altruistic lyrics like “Love’s the greatest thing that we have,” before descending into a fuzzy rock fit on “Bugman.” 13 might sound like a mad scientist’s experiment gone wrong, but it’s the album’s manic energy and wild experimentation that gives it its charm. The chunky, high-pitched vocal morphs and harmonica passages on “B.L.U.R.E.M.I.” and the pulsing, idiosyncratic noise of “Battle” can be interpreted as emblems of the chaotic upending of relationships. Breakups are a chance to take time for yourself and try on a bunch of different hats—and with 13, Blur put on as many sonic hats as they could get their hands on. Songs like “Trailer Park,” “Caramel” and “Mellow Song” reference Albarn and Frischmann’s drug use, which was likely a large point of tension in their relationship. Though “Coffee and TV” was written and sung by guitarist Graham Coxon and doesn’t directly allude to Albarn’s breakup, it represents a similar struggle to return to normalcy, this time referring to Coxon’s relationship with alcohol, and it’s one of Blur’s greatest-ever tracks. —Lizzie Manno

dixie-chicks-fly.jpg14. Dixie Chicks: Fly
Twenty years after this country classic debuted at number one on the Billboard charts, a few truths still hang in the dusty air: Boys will always take you on a “wild goose chase,” a bird can’t sing when you’ve “tied its wings” and Earl had to die. Fly is a perfect country album because it has everything you could ever ask for in a country album: heartache, hilarity and hell’s bells, all conveyed through impeccably told and sung stories. It boasts a barnful of jubilant hootenannies, like the just-for-fun take on “9 to 5,” “Some Days You Gotta Dance,” and the promiscuous rebound anthem “Sin Wagon” (“that’s right, I said mattress dancin’”). But it also has its share of classic country heartbreak ballads à la George Jones or Tammy Wynette—there are two songs called “Hello Mr. Heartache” and “Heartbreak Town,” for pete’s sake, as well as the lonesome “Without You,” and if-you-love-him-let-him-go loveletter “Let Him Fly.” While it’s country through and through, Fly briefly pivots to alt-rock (“Cold Day in July”) right before perfecting the murder plot of the decade in “Goodbye Earl.” The Celtic/country mashup “Ready To Run” is as smart and sassy as anything in the Dixie Chicks’ catalogue, but there’s no doubt as to which Fly song has the most staying power: “Cowboy Take Me Away,” a master thesis in three-part harmony, is a certified classic. At the end of the day, Natalie Maines, Martie Maguire and Emily Erwin Robison are big-hearted dreamers with the voices of angels, and the Wild West romance of “Cowboy Take Me Away” has as much beauty and feeling as your favorite romance movie. —Ellen Johnson

rage-la.jpg13. Rage Against the Machine: The Battle of Los Angeles
Rage Against The Machine brought revolution to the forefront of commercial rock in a time when politics had taken a backseat on the charts. RATM, much like Orwell’s protagonist Winston Smith, were disillusioned with systemic flexes of absolute power. Their 1999 record The Battle of Los Angeles coincided with many politically tense events—Bill Clinton’s deregulation of Wall Street, the continued Zapatista rebellion in Chiapas and the WTO riots (or “The Battle In Seattle”) that sought to tear down corporate hegemony. Los Angeles itself was still healing from the Rodney King Riots in 1992, which makes frontman Zack de la Rocha’s references to 1984 all the more poignant. At the end of “Testify,” de la Rocha gravely intones the (paraphrased) slogan of the novel’s Party: “Who Controls the Past Now, Controls the Future, Who controls the Present Now, Controls the Past.” —Madison Bloom

fiona-pawn.jpg12. Fiona Apple: When The Pawn…
French pop star Chris (aka Christine and the Queens) tweeted the following on Aug. 14: “Can I text Fiona Apple I need advice.” It may seem funny to frame a pre-Twitter album with a modern-day tweet, but When the Pawn… is one of those records that cropped up during the internet’s rise and has only become more buried in our collective online conscious since. Unfortunately there’s no Fiona Apple Hotline, but Chris, like so many of us, has surely found some solace in the fierce singer/songwriter’s second studio album, which broke the record for longest album title (a 90-word poem written by Apple) upon its release in 1999. But Fiona gets straight to the point on the opening track: “You’re all I need, You’re all I need,” she repeats on “On The Bound,” a melancholic twist on the free-for-all conquests one might associate with a romantic rebound. Throughout the album Apple switches off between the wizened therapist and the distressed patient on the other side of the phone. She’s in love, then she’s in pain. She’s weary, then she’s invorgated. She’s wishful (“Paper Bag”), scornful (“Fast As You Can”) and somehow still sultry throughout. On 1996’s Tidal, Fiona Apple flew in on a hurricane, sad and angry and “Slow Like Honey” all at once. But on When The Pawn… she truly arrived, not only as a more self-aware artist, but as a friend. Fiona Apple is the eternal caretaker of our moods, and while all four of her albums deal beautifully with intense feelings, none do it quite like the lamplit journey that is When The Pawn…. —Ellen Johnson

prince-paul-thieves.jpg11. Prince Paul: A Prince Among Thieves
In the past, Prince Paul has attempted to help thread a storyline through one of the albums he produced (De La Soul Is Dead, Gravediggaz’ 6 Feet Deep) but on his second solo joint, the New Yorker arrived with a full-blown concept record; an epic worthy of Pete Townshend and Mike Skinner. With his signature wit, deep library of samples and a dizzying list of guest shots, Paul and his chosen mouthpiece Breezely Brewin tells the story of a young rapper who falls into the drug trade. There’s no proselytizing involved, just sharp storytelling worthy of a great blaxploitation flick and some of Paul’s densest beats. That he was able to coax everyone from Everlast to Xzibit to Chris Rock to Kool Keith along to help tell this tale should tell you everything about Prince Paul’s standing in the hip-hop community. Twenty years later, we’re still waiting for the sequel. —Robert Ham

beck-midnight.jpg10. Beck: Midnight Vultures
Midnight Vultures may just have been ahead of its time. The kind of album to land on both “best” and “worst” lists, it features some of Beck Hansen’s loosest, funkiest songs. No longer the “Loser,” there’s still an air of disassociation from the celebratory themes, keeping the listener guessing how much of the album is meant as a joke. In that sense it’s a perfect end to the 1990s, reminding me of the Simpsons gag where one kid asks another, “Are you being sarcastic?” “I don’t even know anymore.” But it’s an undeniably, earnestly fun album. Beck cutting loose is still Beck layering the production and making sure every note is in the right place. The album ends with a hidden track, “Debra,” which both sounds like the prototype for Flight of the Conchords’ career and a perfect jam in its own right, a product of the ironic ’90s by an iconic Gen X slacker who was, ironically, never remotely a slacker. —Josh Jackson

mf-69-love-songs.jpg9. The Magnetic Fields: 69 Love Songs
For the full effect, pretend it’s 1998. Think what you could possibly know of Stephin Merritt, who isn’t exactly Beck or even Pavement, a liked-but-not-guaranteed-critical-sale—much less commercial—who’d scraped college radio with his wry, brittle paeans to the moon and trains, sung in a Frankenstein basso over cheap, repetitive Casio equipment. Not even the hangers-on who knew they were onto something could’ve predicted the, yes, 69-track magnum opus that would follow. And certainly against all laws of nature, no one predicted that damn near all 69 would be a great song, wise meditation or perfect send-up. It helps that they can’t possibly all be about love—certainly Claudia Gonson’s in some kind of union in the closing “Zebra” for instance (“Zelda looks lonely/ I want a zebra!”) but the greatest bond of human emotions it ain’t. And of course that’s the point; love isn’t always love just like love songs can’t all be love songs, and right, most of us will gladly take the next best thing. With its impossibly instantaneous trove of classics—”Reno Dakota,” “Yeah! Oh Yeah!” “Love Is Like a Bottle of Gin,” “Sweet-Lovin’ Man,” “Papa Was a Rodeo,” “The Night You Can’t Remember,” “All My Little Words” “Acoustic Guitar,” “Crazy for You (But Not that Crazy)” and the Peter Gabriel-certified “The Book of Love” to name a mere fucking 10—I’m still trying to figure out what 69 Love Songs is the next best thing to. —Dan Weiss

dismemberment-i.jpg8. The Dismemberment Plan: Emergency & I
Washington, D.C., has always been an over-caffeinated city, one where corrupt politicians and lobbyists and their staff are constantly stressed out, transferring that wired-ness out to everyone else in the city by proxy, whether they work in politics or not. That feeling pervades the entirety of The Dismemberment Plan’s masterpiece, Emergency & I, a record that has acted as a soundtrack of sorts for the underpaid and overworked residents of that city ever since. Travis Morrison’s ADHD-vibes perfectly complement songs like “Memory Machine” and “I Love a Magician,” while they give a nervous unease to more down-tempo tracks including “Spider in the Snow” and “The Jitters.” On the moments where everything comes together at once, like on the ending jam of “What Do You Want Me to Say” or the final “Bye!”s of “The City,” you realize that you’re listening to a stone-cold classic, a record that sounds just as fresh today as it did 20 years ago. —Steven Edelstone

soft-bulletin.jpg7. The Flaming Lips: The Soft Bulletin (1999)
The loss of a member can hobble even the most creative and ambitious band, but Ronald Jones’ 1996 departure only freed the Flaming Lips to explore weirder, wilder sounds. Their first offering, the four-disc Zaireeka, only hinted at the great leap forward they would make with their 1999 opus The Soft Bulletin, one of the best and biggest-hearted albums of the decade. The synths sounded like an alien symphony and Steve Drozd’s drums pound as passionately as ever, but Wayne Coyne is the real stargazer here. He pens unabashed mash notes to his bandmates, sympathizes with fatigued superheroes, chases lightning bugs around a shameless hook, and dreams up a beautiful metaphysic that keeps the album sounding as fresh and wide-eyed as Pet Sounds or Song Cycle.—Stephen M. Deusner

white-stripes-st.jpg6. The White Stripes: The White Stripes
Here’s an idea: Create a blues-rock album after almost a decade of grunge and punk dominance, cover legends like Robert Johnson, Bob Dylan and the traditional “St. James Infirmary Blues”—oh, this will also be your debut album. Jack and Meg White—they were married, not siblings, in case you never figured it out—did just that, and undoubtedly succeeded at creating something that was new, yet still rooted in the history of music. The formula was simple: guitar, vocals, drums and sometimes a piano. And with those elements, they paid homage to the legend Robert Johnson with “Stop Breaking Down” (previously covered by The Rolling Stones) and to Dylan with “One More Cup of Coffee.” With original tracks like “I Fought Piranhas” and “The Big Three Killed My Baby,” which points a finger at Detroit’s auto industry, the Whites proved they could create, and not just mimic, blues music. We all know now The White Stripes was just the beginning for this odd couple, and looking back now, their success and influence on music is obvious. —Clint Alwahab

tom-waits-mule.jpg5. Tom Waits: Mule Variations
Tom Waits’ wickedly cool persona and sharp wit can make you forget just how deeply empathetic his songs can be, and no where is this more true than on Mule Variations. The characters that populate the songs here might have walked out of the same fever-dream carnival, but their stories mine the depth and breadth of the human condition. There’s hope here in songs such as the hymn-like “Come on up to the House.” Along with wife and co-writer Kathleen Brennan, Waits crafts some of his most beautiful ballads alongside his trademark cacophonies like “Filipino Box Spring Hog” and “Big in Japan” (featuring Les Claypool on bass). Marc Ribot’s guitar provides the perfect idiosyncratic counterpoints to the memorable melodies, and Waits’ whiskey-drenched vocals power through the noise. Illustrating just how hard his music is to categorize, Mule Variations won the Grammy award for Best Contemporary Folk Album and also garnered a nomination for Best Male Rock Vocal Performance. Whatever genre you want to tie it to, the album remains a masterpiece. —Josh Jackson

roots-fall.jpg4. The Roots: Things Fall Apart
Tariq “Black Thought” Trotter and Ahmir “?uestlove” Thompson founded The Roots in 1987, helping redefine what hip hop would become. From their early jazz-based beginnings to their first-ever concept album, The Roots’ influence is nothing short of legendary. With Things Fall Apart, The Roots stood halfway between the jazz-influenced grooves prevalent throughout their ’90s work and their more accessible albums of the past decade. The result is the best of both worlds musically as The Roots began building a legacy. —Max Blau

sigur-ros-agaetis.jpg3. Sigur Rós: Ágætis byrjun
With their second album, Ágætis byrjun, Iceland post-rockers Sigur Rós began to draw attention outside of their sparsely-populated native country. Though it was originally released in 1999, it wasn’t out in the U.S. until 2001, but it became the group’s critical and commercial breakthrough. As soon as you hear the breathtaking falsetto Jón Þór Birgisson on “Svefn-g-englar,” you know you’re in for an extremely meditative, delicately hand-crafted and awe-inspiring record. The track’s sweeping grandeur is how you’d imagine a cocoon or life in the womb to feel—nurturing, warm, blissfully carefree and a beautiful feat of nature. Most of these tracks are sprawling (many surpass the seven-minute mark), but you won’t tire of their comfort and elegance. The album meshes together post-rock, ambient, dream-pop, classical and shoegaze in a way that doesn’t feel too avant-garde or indulgent—it’s the deep emotional sentiment drawn out from these lengthy pieces and their mythical lyrical imagination that preserves its humanity. The string arrangements on “Staralfur” are devastatingly gorgeous as its lyrics describe a young child dozing off under the covers in the presence of an unexpected visitor—a “staring elf” (also the title of the song). The slow yearning and syrupy ambience of “Flugufrelsarinn” is a vigorous wave while the jazzy horns, minimal vocals and stark cymbals of “Ný batterí” are glaring contrast to the song’s violent yet poetic imagery (“My soul has grown rusty / The electricity is gone / I want to cut / And slice myself to death / But daren’t risk it / Instead I turn myself off”). —Lizzie Manno

wilco-summerteeth.jpg2. Wilco: Summerteeth
While not quite the behemoth that 1996’s lauded double-disc, Being There, was, Wilco’s third studio album still had a whopping 17 songs (including bonus tracks). Summerteeth remains the sunniest of the band’s records, even as their sonic exploration began. Individual songs like “She’s a Jar” and the Henry Miller-inspired “Via Chicago” revealed elements of depression and social frustrations. Nonetheless, Summerteeth shines though its dark lyrics, as the melodies of “A Shot in the Arm,” “I’m Always In Love” and “ELT” revive listeners and strike the perfect balance of contradictions for a band in transition. —Hilary Saunders

built-keep.jpg1. Built to Spill: Keep It Like A Secret
Built to Spill essentially has two fanbases, the indie-pop kids who loved 1994’s There’s Nothing Wrong With Love and the fans of rock god virtuosity who consider 1997’s sprawling Perfect From Now On to be truly perfect. 1999’s Keep It Like A Secret is the band’s best album because it falls perfectly in-between those two extremes. It’s full of amazingly catchy rock songs with fantastic guitar work and Doug Martsch’s nostalgic lyrics and elegiac, Neil Young-ian voice. —Garrett Martin

Listen to Josh Jackson and Ellen Johnson on the best albums of 1999 on The Paste Podcast below, or better yet, download on iTunes, Google Play, Stitcher, Spotify or the new app from our podcast partner Himalaya, and subscribe!

Share Tweet Submit Pin