The Best Albums Of 1999: 55 Records Worth Revisiting

To say that 1999 was a year of excitement and uncertainty would be an understatement. The world waited expectantly on the cusp of the new millennium and, in the months leading up to Y2K, music fans had plenty of albums to enjoy.

While the pop landscape was flush with a broad array of boy bands, girl groups, and pop divas (including Destiny’s Child, Britney Spears, Backstreet Boys, and Christina Aguilera), the airwaves were also brimming with Latin rhythms. Buena Vista Social Club, a documentary about the Cuban music scene, gave legendary artists like Ibrahim Ferrer a new platform. Latin rockers Santana found a new generation of fans with their massively popular comeback album, Supernatural. Rising acts like Zurdok and Control Machete found new opportunities for crossover success, while Ricky Martin had everyone “Livin’ La Vida Loca.”

The air was ripe with possibilities for electronic acts as well, with Moby, Fatboy Slim, and Underworld finding mainstream success, while hip-hop fans had plenty of incredible music to choose from, thanks to great albums by Dr. Dre, The Roots, and Eminem.

From the Red Hot Chili Peppers’ Californication to TLC’s Fanmail, here are the best albums of 1999.

Can’t get enough 90s music? Listen to our 90s Music playlist here.

55: Julie Miller – Broken Things

The country-folk singer’s 1999 album is an emotional and intimate record that puts her stirring vocals and precise songwriting front and center.

54: Pépé Bradock – Burning

Taking inspiration from dance music of the 70s, the French producer’s influential work spins disco, breakbeats, and soul into an irresistibly danceable record.

53: Beck – Midnite Vultures

Taking inspiration from soul and funk music, the genre-blending artist’s 1999 album injects the styles with a humor and quirkiness distinctly his own.

52: Ibrahim Ferrer – Buena Vista Social Club Presents Ibrahim Ferrer

A follow-up album to the music documentary of the same name, the Cuban music legend’s comeback album revives the spirit of the golden age of Cuban music in the 50s and 60s.

51: Zurdok – Hombre Sintetizador

The Mexican alt rock band’s 1999 album is home to the hit single “Abre Los Ojos,” and established the band as one of the most popular regional bands of the decade.

50: Botch – We Are the Romans

The metalcore band’s final album incorporates experimental rhythms and esoteric lyrics to create a standout album of the niche genre.

49: Puya – Fundamental

The Puerto Rican metal band’s major label debut put rock en espanol on the map and proved that good music is a universal language.

48: The Chemical Brothers ‎– Surrender

The electronic duo turned to house music for their third studio album, threading the needle between the storied genre and the big beat sound they helped pioneer in their earlier releases.

47: Dillinger Escape Plan – Calculating Infinity

The metalcore band’s debut album is full of loud rage and technical detail, becoming one of the most inventive and influential releases of the genre.

46: Reba McEntire – So Good Together

Home to the crossover single “What Do You Say,” the prolific country star’s 25th studio album introduced her to a broader audience and cemented her status as a living legend.

45: Paul Bley, Gary Peacock, Paul Motian – Not Two, Not One

The jazz masters reunited after over two decades on this record which feels like a well-deserving victory lap and beautifully plays to their respective talents.

44: Opeth – Still Life

The Swedish metal band’s concept album has some of their best lyricism and memorable arrangements, establishing them as leading lights of the scene.

43: The Olivia Tremor Control – Black Foliage: Animation Music Volume One

Taking inspiration from musique concrète, noise, and pop, the band’s 1999 album eschews any easy categorization and will keep your head spinning from start to finish.

42: Dream Theater – Metropolis Pt. 2: Scenes from a Memory

The prog rock band’s 1999 concept album centers around a time-traveling murder mystery with music just as dense as the narrative. For patient listeners, the reward is great.

41: Underworld – Beaucoup Fish

After getting a big boost from a placement in the film Trainspotting, the group’s highly anticipated album exceeded expectations and became an instant electronica classic.

40: Moby – Play

Moby’s commercial smash streaks techno with hints of blues and pop, creating a sound that is both critically remarkable and widely accessible.

39: Dave Holland Quintet – Prime Directive

The famed double-bassist delivers pure, unadulterated jazz on this album – improvisational, meditative, and undeniably rhythmic.

30: Blur – 13

On this album Damon Albarn’s songwriting centers on the dissolution of relationships, producing one of the group’s most vulnerable records.

38: Prince Paul – A Prince Among Thieves

Featuring the likes of Big Daddy Kane, Biz Markie, Chris Rock, and De La Soul, the hip-hop producer’s concept album is a detailed and extremely rich model of musical storytelling.

37: The Beta Band – The Beta Band

The rock band’s 1999 album brings together pop, rock, hip-hop, folk, and much more for a chaotically beautiful debut.

36: Control Machete – Artilleria Pesada Presenta

The Mexican hip-hop group’s second album established them as a mainstay in Latin pop and opened the door for a number of cross-genre collaborations.

35: Macy Gray – On How Life Is

Home to favorites, “I Try” and “Still,” the distinctly bluesy rasp of Macy Gray was introduced to the world on this debut album.

34: TLC – Fanmail

The influential girl group’s third studio album includes the smash hit, “No Scrubs,” and would be the last album released during Lisa “Left Eye” Lopes’ lifetime.

33: Ginuwine – 100% Ginuwine

The singer’s Timbaland-produced album reshaped the sound of R&B by blending traditional soul with futuristic production.

32: Blackalicious – Nia

The Sacramento hip-hop duo’s debut album is at turns whimsical and abstract but always feels rooted in the tenets of underground hip-hop – booming beats and great rhymes.

31: Mary J. Blige – Mary

The R&B singer broke from her hip-hop roots on this album, showing that she has the vocal chops to tackle soul, traditional R&B, and pop.

30: Susumu Yokota – Sakura

The Japanese producer’s excellent ambient album doesn’t hide in electronic instrumentation, using it instead to highlight the beauty of simple guitars and piano.

29: Dr. Dre – 2001

Home to hip-hop classics like “Still D.R.E” and “Forgot About Dre,” the legendary producer and rapper’s comeback album took him from behind the boards and re-established him as a frontman of the genre.

28: Basement Jaxx – Remedy

Taking cues from New York’s house music scene, the British electronic duo’s debut album is a groovy, stylistically diverse take on dance music that will keep you moving from top to bottom.

27: Christina Aguilera – Christina Aguilera

Home to timeless hits like “Genie In A Bottle” and “What A Girl Wants,” the singer’s debut album established her as a vocal powerhouse with a knack for catchy songwriting.

26: Esbjörn Svensson Trio – From Gagarin’s Point Of View

Featuring the memorable title track, the jazz trio’s international breakthrough brought their distinct brand of jazz pop to a global audience.

25: Alison Krauss – Forget About It

Featuring fan favorites like “Ghost In This House” and “Stay,” the bluegrass singer’s stripped down 1999 album serves as a showcase for her masterful storytelling.

24: Neurosis – Times of Grace

One of their most fully realized projects, the Oakland death metal band’s uncompromising and challenging 1999 album is not for the faint of heart, but if you can get into it, you’ll never look back.

23: Backstreet Boys – Millennium

Home to the pop classic, “I Want It That Way,” the boy band’s third studio album catapulted them to global stardom.

22: Built to Spill: Keep It Like A Secret

Lead singer and songwriter ​​Doug Martsch turned to pop for the band’s second big label album, nevertheless he managed to pull off a more mainstream sound without having to hand over the group’s indie rock cred.

21: Drexciya – Neptune’s Lair

Steeped in mythology and mystery, the influential electronic duo’s debut LP sounds like nothing before it and is widely considered to be one of the greatest techno records ever produced.

20: Nine Inch Nails – The Fragile

Trent Reznor’s meticulous approach to arranging music reaches a creative peak on this record that encompasses everything from industrial noise to ambient instrumentals.

19: Rage Against The Machine – The Battle Of Los Angeles

Home to their biggest hit ​​”Guerilla Radio,” the rapping rock band’s 1999 album still sounds as revolutionary today as it did decades ago.

18: Red Hot Chili Peppers – Californication

Featuring the title hit and the Grammy Award-winning “Scar Tissue,” the band’s 1999 album saw them reuniting with guitarist John Frusciante and became one of their most successful releases to date.

17: Santana – Supernatural

The Latin rock band’s comeback album for Arista Records features some high-profile guests like Lauryn Hill, Eagle Eye Cherry, and Eric Clapton, and returned the veteran rockers to the public eye.

16: Nobuo Uematsu – Final Fantasy VIII

The video game soundtrack has taken on a life of its own, allowing longtime gamers and nongamers alike to find something to enjoy.

15: Ely Guerra – Lotofire

Spanning topics as serious as femicide and environmentalism, the Mexican singer’s hit album is a subtle yet potent record that showcases her understated vocals over trip-hop inspired production.

14: Mariah Carey – Rainbow

Including the forever party jam, “Heartbreaker,” the vocal titan’s seventh studio album is a pop R&B classic that conjures puppy love and summer days.

13: Dixie Chicks – Fly

The country group’s chart-topping album includes hits like “Ready to Run,” and “Cowboy Take Me Away.” With its diverse influences and sharp storytelling, the record paved the way for future female country pop stars like Taylor Swift.

12: Smog – Knock Knock

Bill Calahan’s affecting break-up album is understated, bittersweet, and utterly hopeful, showing that even in crisis, there is light to be found.

11: Kelis – Kaleidoscope

The pop R&B icon’s debut album was produced by the Neptunes, heightening the out-of-this-world energy of Kelis’s vocal delivery and daring storytelling.

10: Destiny’s Child – The Writing’s on the Wall

Featuring classics such as “Say My Name,” “Bills, Bills, Bills,” “Bug A Boo,” and “Jumpin’ Jumpin’,” the girl group’s sophomore album proved that they weren’t just pop savvy but also incredible vocalists.

9: The Magnetic Fields – 69 Love Songs

Comprising three volumes of music, Stephin Merritt’s ambitious record rejects surface-level romance and digs deep to uncover the good, the bad, and the ugly of romantic love.

8: Sigur Rós – Ágætis byrjun

With its dense arrangements and gorgeous melodies, the Icelandic band’s sophomore album took post-rock from a small community to a global phenomenon.

7: Sleater-Kinney – The Hot Rock

The rock band turned inward for their fourth album exploring the dark corners of the mind and relationships, showcasing their incredible range and storytelling skills.

6: The Roots – Things Fall Apart

The hip-hop band’s masterpiece is a prescient, invigorating, and critical album that continues to impress hip-hop fans decades after its release.

5: MF Doom – Operation: Doomsday

The late rapper’s opus is a swirl of dense lyricism and stellar production that makes it clear why Doom is your favorite rapper’s favorite rapper.

4: Britney Spears – …Baby One More Time

Home to the record-smashing title hit, the pop queen’s debut album remade the genre in her image and signaled a new era of teen pop stars.

3: The Flaming Lips – The Soft Bulletin

With the grandeur of an orchestra, the rock band’s masterpiece is deeply moving and widely considered to be one of the best records of the decade.

2: Mos Def – Black on Both Sides

Featuring beloved classics like “Ms. Fat Booty” and “UMI Says,” the Brooklyn rapper debut established him as one of the genre’s greatest lyricists.

1: Eminem – The Slim Shady LP

The rap veteran’s sophomore album includes the smash hit, “My Name Is” and introduced Eminem the supervillain to the mainstream; despite its controversy, no one could deny that it was one of the greatest major label debuts of all time.

Can’t get enough 90s music? Listen to our 90s Music playlist here.