Top 50 Hip Hop Albums of 1999 - Must-Hear Classics of the Era!

The year 1999 marked a pivotal moment in the evolution of hip-hop, a time when the genre’s sound and culture were expanding in bold new directions.

From underground gems to mainstream smashes, the top albums of 1999 showcased a diverse range of voices, blending lyricism, innovation, and social commentary in ways that would shape the future of hip-hop.

In this article, we dive into the 40 most influential and game-changing hip-hop albums of 1999. Ready to revisit the golden year? Keep reading to discover which albums defined the era.

1. Mos Def – Black on Both Sides (1999)

Black on Both Sides marked a pivotal moment in Mos Def’s career, showcasing his full creative potential beyond his work with Black Star.

The album blends diverse production styles with Mos’s insightful lyrics, exploring everything from social issues to personal reflection.

From soulful tracks like “Umi Says” to raw hip-hop anthems like “Mathematics,” Mos Def proves his ability to weave musical and lyrical innovation into a cohesive masterpiece that stands the test of time.

Key Songs:

• Umi Says
• Mathematics
• Do It Now
• Fear Not of Man

2. The Roots – Things Fall Apart (1999)

Things Fall Apart is a defining album in The Roots’ discography and a milestone in the evolution of conscious hip-hop.

The album combines live instrumentation with a raw and emotive approach, led by Black Thought’s powerful lyrics and Questlove’s dynamic drumming.

With standout tracks like "You Got Me" featuring Erykah Badu, The Roots successfully blended jazz, soul, and hip-hop to create a sound that was both innovative and timeless, earning their place as one of the most influential groups of the era.

Key Songs:

• You Got Me
• The Next Movement
• Act Too (Love of My Life)

Also Read: Stop The Violence Movement – Self Destruction Lyrics

3. Various Artists – Rawkus Presents: Soundbombing II (1999)

A defining compilation from the Rawkus label, Soundbombing II captures the raw energy and innovation of late 90s underground hip-hop.

The album introduced a new wave of artists, including Pharoahe Monch, Mos Def, and Black Star, with tracks that blended gritty boom-bap beats and thought-provoking lyrics.

The seamless flow between different artists, combined with impeccable production, made this album a classic in the underground scene and a pivotal moment for the Rawkus label's rise to prominence.

Key Songs:

• WWIII
• Thieves in the Night
• Next Up

4. Dr. Dre – 2001 (1999)

2001 was a sonic shift for Dr. Dre, marking his reinvention from the G-funk era to a more aggressive, hard-hitting sound that redefined West Coast hip-hop.

The album’s production, featuring beats that were more aligned with boom-bap, set the stage for the sound of the 2000s.

With memorable guest appearances from Snoop Dogg, Eminem, and Nate Dogg, 2001 was an instant classic, pushing Dre’s legacy further into the mainstream and cementing his status as a hip-hop mogul.

Key Songs:

• Forgot About Dre
• The Next Episode
• Still D.R.E.

5. Prince Paul – A Prince Among Thieves (1999)

Prince Paul's A Prince Among Thieves is a masterful concept album that blends skits and songs to tell a compelling, cinematic story.

Centering on Breezly Brewin, a rapper who gets pulled into a world of crime, the album features an all-star cast of guest appearances, including Kool Keith, Big Daddy Kane, and De La Soul.

With its narrative-driven structure and exceptional production, this album stands out as one of the best concept albums in hip-hop history, blending storytelling with top-tier beats.

Key Songs:

• The Chase
• The Horror
• Peepin’ The Game

6. Blackalicious – Nia (1999)

Nia, Blackalicious’s debut album, fuses thoughtful lyricism with jazzy, experimental beats. Led by the unparalleled flow of Gift of Gab, the album is both cerebral and uplifting, blending conscious themes with intricate wordplay.

Tracks like “Alphabet Aerobics” became iconic for their technical brilliance, while the album as a whole evokes the spirit of 70s jazz and pro-black consciousness.

A standout in the underground hip-hop scene, Nia helped set the stage for the rise of more introspective and alternative sounds in the 2000s.

Key Songs:

• Alphabet Aerobics
• Making Progress
• A to G

7. Pharoahe Monch – Internal Affairs (1999)

Internal Affairs was Pharoahe Monch’s highly anticipated solo debut, following his success with Organized Konfusion. The album showcases his incredible lyrical dexterity and unique flow, solidifying him as one of the most technical MCs in hip-hop.

With standout tracks like "Simon Says," which became a staple in hip-hop clubs, Monch delivers a hard-hitting, no-frills approach to rap.

The album’s production, while not overly experimental, provides the perfect backdrop for Monch's intricate lyricism, making it an essential listen for hardcore hip-hop fans.

Key Songs:

• Simon Says
• The Truth
• Clap

8. Eminem – The Slim Shady LP (1999)

The Slim Shady LP introduced Eminem to the world in a way that could not be ignored. A mix of dark humor, outrageous lyricism, and unmatched technical skill.

The album captured the attention of the mainstream thanks to Eminem's wild persona and the endorsement of Dr. Dre. Despite its controversial content, it showcased Eminem’s complex storytelling and rapid-fire delivery, pushing the boundaries of what could be said in rap.

With Dre’s impeccable production and Em's ability to craft surreal, often disturbing narratives, this album became an instant classic. Though it may not be perfect, its impact on hip-hop in 1999 and beyond is undeniable.

Key Songs:

• My Name Is
• Guilty Conscience (feat. Dr. Dre)
• Role Model
• Just Don't Give a F***

9. MF DOOM – Operation: Doomsday (1999)

Operation: Doomsday marked the debut of the elusive MF DOOM, a project that would later become iconic in the underground hip-hop world.

With his unique blend of comic book references, eccentric lyricism, and raw, metallic production, DOOM crafted an album that felt both old-school and futuristic.

His distinctive flow, coupled with the sample-heavy, minimalistic beats, helped define an era of underground rap that would evolve in the years to come.

While Operation: Doomsday may not have had immediate mainstream appeal, its cult following and influence on the genre are immeasurable.

Key Songs:

• Doomsday
• Rhymes Like Dimes
• The Finest
• Go With the Flow

10. Jay-Z – Vol. 3... Life and Times of S. Carter (1999)

Vol. 3 finds Jay-Z in full control of his sound and influence, delivering some of the sharpest verses of his career.

The album blends street narratives with introspective moments, while production from Timbaland, Swizz Beatz, and DJ Premier provides a fresh backdrop.

Jay’s command of both lyrics and flow is unparalleled, cementing his place as one of the leading figures of the era.

Tracks like “Big Pimpin’” became instant classics, furthering his mainstream success, while the album’s eclectic sound showcased his ability to evolve with the times.

Key Songs:

• Big Pimpin' (feat. UGK)
• Do It Again (Put Ya Hands Up)
• So Ghetto
• S. Carter

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11. B.G. – Chopper City in the Ghetto (1999)

Chopper City in the Ghetto represents a key moment in the Cash Money Records catalog and the southern hip-hop movement.

Lead by B.G., the album blends hard-hitting beats from Mannie Fresh with B.G.’s streetwise lyricism, laying the foundation for the Cash Money dynasty.

While some purists dismissed the album for its flashy, commercial content, its unique production and catchy hooks made it a regional hit.

The iconic single “Bling Bling” perfectly captures the album’s themes of luxury and excess, and its influence is still felt in the rap world today.

Key Songs:

• Bling Bling
• Get It How U Live
• I Need a Hot Girl
• Cash Money Is an Army

12. Lootpack – Soundpieces: Da Antidote! (1999)

A true underground gem, Soundpieces: Da Antidote! introduced the world to Madlib’s distinctive production style, a blend of dusty loops, jazz influences, and boom-bap drums.

While the rapping on the album is straightforward, it’s the beats that truly stand out, showcasing Madlib’s early potential as a producer.

Featuring guest appearances from Dilated Peoples and other underground artists, this album paved the way for Madlib’s rise to prominence in the 2000s, marking the start of a legendary career in hip-hop production.

Key Songs:

• The Anthem
• Strange Ways
• Step Away
• Next Episode

13. Handsome Boy Modeling School – So... How's Your Girl? (1999)

A collaboration between Prince Paul and Dan the Automator, So... How's Your Girl? is an eclectic concept album that blends hip-hop with elements of electronic, trip-hop, and downtempo music.

The album features a star-studded lineup of guest artists, including Del the Funky Homosapien, Prince Paul himself, and others.

While its tongue-in-cheek "modeling" concept could have easily been a gimmick, the album’s strong production and diverse sound kept it fresh and engaging.

Tracks like "Megaton B-Boy 2000" show the duo’s ability to push boundaries while keeping things fun and innovative.

Key Songs:

• Nitty Gritty
• The Truth
• Megaton B-Boy 2000
• If It Wasn't for You

14. Q-Tip – Amplified (1999)

Amplified represents a departure from Q-Tip’s previous work with A Tribe Called Quest, showcasing a more polished, modern sound with production heavily influenced by J Dilla.

The album features smooth, jazzy beats that were ahead of their time, blending with Q-Tip’s laid-back delivery.

Despite being a commercial effort, Amplified carries the same thoughtful approach to lyricism and production that fans had come to expect from Q-Tip.

With a unique balance of laid-back vibes and innovative production, the album holds up surprisingly well over time.

Key Songs:

• Vivrant Thing
• Breathe and Stop
• Let's Ride
• Go Hard or Go Home

15. Mobb Deep – Murda Muzik (1999)

While Murda Muzik doesn't immediately hit with the same intensity as its predecessor, Hell on Earth, it’s an album that deepens the more you listen to it.

The production, while not as grimy or aggressive as Hell on Earth, still carries that signature Mobb Deep dark vibe, thanks to Havoc's beats.

The chemistry between Prodigy and Havoc is undeniable as they continue to deliver their gritty street narratives with a poetic, yet hard edge. Although it doesn’t break new ground in terms of lyrical content, it showcases their talent for crafting vivid tales of street life.

The standout feature is their chemistry on the mic, which carries the weight of the album. The beats here aren’t as crushing as their previous work, but they still suit the duo's flow.

The inclusion of a couple of tracks from The Alchemist adds a fresh flavor to the mix, offering a glimpse into what would later become his signature sound.

This isn't necessarily where newcomers should start with Mobb Deep, but for long-time fans, it's a rewarding listen that holds up over time. Unfortunately, after Murda Muzik, their later work, especially Infamy, would not quite measure up to this standard.

Key Songs:

• Quiet Storm
• Hell on Earth (Front Lines)
• The Learning (Burn)
• It's Mine

16. The High & Mighty – Home Field Advantage (1999)

The High & Mighty’s Home Field Advantage may not get the same attention as other Rawkus releases from the era, but it holds a special place in the hearts of those who remember the late '90s underground hip-hop scene.

Released in 1999, it’s a perfect snapshot of that time—offering rugged East Coast beats, clever lyrics, and a sense of fun. Mr. Eon’s rapping may not be for everyone, but his lighthearted delivery and humorous lines add to the charm of the album.

The production stands out with its hard beats, scratches, and a heavy influence of '90s boom-bap. It doesn’t reinvent the wheel, but it’s solid, nostalgic hip-hop.

Even though it might not have the same widespread praise as Soundbombing II or Black Star, Home Field Advantage remains an underrated gem for fans of the genre.

Key Songs:

• B-Boy Document '99
• The Truth
• Pimp Slap
• Home Field Advantage

17. Hot Boy$ – Guerrilla Warfare (1999)

Guerrilla Warfare is one of the standout releases from Cash Money Records during its heyday, and a defining album for the label’s rise in the late '90s.

With Mannie Fresh’s signature production, layered beats, and infectious hooks, the album showcases the collective talents of Juvenile, Lil' Wayne, B.G., and Turk.

While each member has their moment to shine, it’s Juvenile and Lil' Wayne who steal the show with their sharp delivery and lyrical creativity.

Lil' Wayne’s verses here show a young rapper with loads of promise, a far cry from the complex, abstract style he would later adopt.

The album’s blend of catchy hooks, street tales, and Mannie Fresh’s booming production made it a must-have for fans of Southern hip-hop. It's a powerful album that helped cement Cash Money's place at the forefront of rap during the '90s.

Key Songs:

• Blaze Up
• We on Fire
• I Need a Hot Girl
• Cash Money Is an Army

18. Method Man & Redman – Blackout! (1999)

Blackout! is a quintessential collaboration between two of hip-hop’s most dynamic MCs, Method Man and Redman.

While the album may have initially disappointed some fans due to its departure from the traditional Wu-Tang sound, it still delivers a fun, high-energy project that capitalizes on their fantastic chemistry.

The dynamic between the two MCs is the standout feature here, with each verse often sparking a competitive back-and-forth that elevates the entire album.

The beats, though mostly handled by Erick Sermon, are tight and keep the focus on the rapping. The album is light on concept but full of character, boasting strong performances from both Meth and Red, making it essential for their fans.

Key Songs:

• Y.O.U.
• Da Rockwilder
• How High (Remix)
• 1,2, 1,2

19. Muzion – Mentalité moune morne... (Ils n’ont pas compris) (1999)

Muzion’s Mentalité moune morne represents a pivotal moment in the rise of Quebec's hip-hop scene, and it remains an essential album for anyone interested in the evolution of French-language rap.

The album blends intelligent lyricism with strong political and social commentary, addressing themes of inequality and urban struggles in Montreal.

The group’s three MCs—Dramatik, Imposs, and J.Kyll—are all standout performers, with Dramatik's flow being particularly notable.

The production on the album is varied but remains true to an East Coast influence, making the sound feel both fresh and familiar.

The album’s impact in the late '90s Montreal hip-hop scene is still felt today, and it’s a great representation of the genre's potential in Quebec.

Key Songs:

• Mentalité Moune Morne
• L'Histoire d'un rêve
• Ce n'est pas de la démagogie
• Rien à prouver

20. Arsonists – As the World Burns (1999)

As the World Burns by Arsonists is a fast-paced, punchline-heavy album that represents the gritty, underground side of East Coast hip-hop.

The group’s focus is on pure, lyrical dexterity, with a barrage of clever verses and punchlines coming from every corner. The production complements the intensity of the rapping, with dark, banging beats that drive the energy of the album.

The album is not for casual listeners, as its non-stop barrage of intricate verses and lack of hooks may turn off newcomers.

However, for fans of pure lyricism, As the World Burns delivers exactly what it promises: relentless rapping and strong, cohesive production.

While the second half of the album loses a bit of steam, the first half is an excellent example of late '90s East Coast hip-hop, and the album holds up well over time.

Key Songs:

• Backdraft
• Flame On
• Incendiary
• Worldwide

21. Kurupt – Tha Streetz Iz a Mutha (1999)

Kurupt's Tha Streetz Iz a Mutha stands as one of the best West Coast gangsta rap albums of the late '90s. After the mixed reception of his Kuruption! double album, Kurupt returns strong with a more focused, high-energy effort.

The album boasts strong production and guest appearances, helping to solidify his status as one of the West Coast's top rappers.

The beats here are varied and fresh, with contributions from Organized Noize adding a unique touch to the album’s sound.

While Kurupt is the main star, the posse dynamic works well, and the guest verses complement his flow. It’s a cohesive album with no weak tracks and is an essential listen for any fan of West Coast hip-hop.

Key Songs:

• Who Ride Wit Us
• It Ain’t Nothin’
• Loco
• Nothin’ but the Cavi Hit

Check Now: Top 50 Hip Hop Albums 2001 – Must-Hear Classics Ranked!

22. Nas – I Am... (1999)

When I Am... was first released in 1999, it was widely loved by fans, yet over time, opinions have become more divided, especially online.

The album captures the digital production style that defined much of late '90s New York rap—moving away from the sampled boom-bap of the mid-'90s.

Though some of the beats might sound dated today, Nas’s sharp lyricism and impressive storytelling still shine through. His rapping is top-tier on this album, delivering some of his best verses, including tracks like Nas Is Like (which many consider one of his greatest songs).

While it isn’t a flawless project, I Am... remains a significant piece of Nas’s catalog, with its smooth mix of street narratives and introspective lyricism.

It’s a must-listen for fans who enjoy Nas beyond Illmatic, offering a unique glimpse into the changing landscape of hip-hop during 1999.

Key Songs:

• Nas Is Like
• Hate Me Now
• Undying Love
• New York State of Mind Pt. II

23. The Notorious B.I.G. – Born Again (1999)

Released posthumously, Born Again often gets criticized as a cash-in project from Puff Daddy, filled with guest features and previously unreleased Biggie verses.

Despite these criticisms, the album is actually a solid listen, thanks to Biggie's timeless delivery. The production, though uneven at times, features some standout tracks, like Dead Wrong and Who Shot Ya?,

The latter of which was a b-side anthem long before the album's release. Even though the inclusion of recycled verses (like on I Really Want to Show You) may feel repetitive.

The quality of Biggie’s presence on the mic and the strong guest appearances make this album worth checking out for any fan of the Notorious B.I.G. It's a good, enjoyable project, despite its flaws.

Key Songs:

• Dead Wrong
• Who Shot Ya?
• Big Booty Hoes
• Rap Phenomenon

24. Sans Pression – 514-50 dans mon réseau (1999)

514-50 dans mon réseau was another landmark release for Quebec's hip-hop scene in 1999. Alongside Muzion, Sans Pression helped define the province’s rap identity, blending local street stories with universal themes.

The album’s impact in Quebec was huge—especially because it resonated with listeners who could relate to the raw, unfiltered lyrics, even if they weren’t living the "street life" themselves.

While the production feels a bit dated in retrospect, the rough, hardcore style complements the album's themes. The first half of the album is particularly strong, while the latter part remains solid but not as impactful.

Sans Pression's unique blend of Quebecois street culture, relatable lyrics, and powerful delivery makes this album an essential part of the province's hip-hop history, even if some elements feel stuck in the past.

Key Songs:

• Pas de bling-bling
• La Ruée vers l’or
• Jeunesse en manque
• C’est dans le sang

25. Black Moon – War Zone (1999)

War Zone stands as a standout in Black Moon’s catalog, even though it doesn’t quite match the perfection of Enta Da Stage.

This album was one of the few in 1999 that maintained a gritty, mid-'90s East Coast sound while staying relevant.

The production by the Beatminerz is solid, continuing the rugged, sample-heavy style that defined Black Moon’s earlier work. Though Buckshot may not be the most technically skilled rapper, he holds it down with his distinct voice and authentic delivery.

The album flows well from start to finish, and while it may not be a classic, it's a strong release for anyone into raw, heavy New York hip-hop.

War Zone may not have achieved the same legendary status as some of its contemporaries, but it remains an album worth checking out for fans of the darker, underground side of East Coast rap.

Key Songs:

• War Zone
• Live @ the Barbeque
• I’m Da Man
• Blood Money

26. Dr. Dooom – First Come, First Served (1999)

Forget about Dr. Octagon—in 1999, it was all about Dr. Dooom. This album marked Kool Keith's best lyrical performance, showcasing his unfiltered rage and some of the craziest rhymes you'll ever hear.

From the opening track "No Chorus," where Keith unloads on wack MCs, his fiery delivery sets the tone for the entire album.

While the production doesn’t hold up as well today, the beats were still effective back in 1999. Keith’s performance is the album’s real highlight, and this marks the beginning of his underground following.

If you're a Kool Keith fan and haven't heard this album, it's essential listening—his 1999 work is a career-defining moment in terms of straight rapping.

Key Songs:

• No Chorus
• The Return of Dr. Dooom
• How U Like Me Now
• Food for Thought

27. Freeman – L'palais de justice (1999)

Freeman, known for his work with IAM, presents a solid solo effort on L'palais de justice. While his unique flow might take some getting used to (he's got a style that’s sometimes hard to follow), the album’s themes are consistent with IAM's—street life, poverty, and social justice.

The production features violins and orchestral elements, which gives the album a somber, introspective atmosphere.

The boom-bap sound was standard for the time, but it holds up well, especially when paired with Freeman’s thoughtful lyrics.

Though not the most innovative album of 1999, L'palais de justice is still a strong release and an essential piece of French hip-hop history.

Key Songs:

• L'palais de justice
• L'homme de l'ombre
• La Rue
• L'élite du pire

28. La Cliqua – La Cliqua (1999)

La Cliqua’s self-titled album is a testament to the power of being a few years behind the latest trends. While the production may not have been cutting-edge in 1999, it stands as a prime example of how to make classic boom-bap beats work.

This album stays true to the gritty, hard-hitting style of 90s New York hip-hop, and the collective’s three MCs—Rocca, Daddy Lord C, and Raphael—shine throughout. The album's one-dimensional sound actually works in its favor, as each track hits hard, making it an impressive listen for its 73-minute runtime.

While it may not have the diversity of other 1999 albums, La Cliqua is one of the best French hip-hop releases of the year.

Key Songs:

• La Vie
• Le Rap de Ma Vie
• Bang
• Même Pas En Rêve

29. Swollen Members – Balance (1999)

Balance represents the raw, underground sound of late-'90s Canadian hip-hop. The Swollen Members' debut album is defined by its dark beats and clever lyricism, with strong guest features from names like Dilated Peoples, Del, and Alchemist.

While the production might sound too underground for some, it’s this very quality that makes the album stand out.

The MCs bring their A-game, with each track dripping with sharp rhymes and a sense of gritty authenticity.

Though the Swollen Members would refine their sound over time, Balance is a solid and underappreciated start. If you're into raw, underground hip-hop, this is a must-have in your collection.

Key Songs:

• Lady Venom
• Black Magic
• Monsta
• Too Late

30. K-Rino – No Mercy (1999)

K-Rino’s No Mercy is one of the darkest and most intense albums of his career. The beats are menacingly dark, giving the album a creepy, almost sinister vibe that suits K-Rino’s lyrical content perfectly.

He brings his razor-sharp, street-smart verses to the forefront, tackling issues of struggle and survival from a perspective of intelligence and insight.

The album is challenging but rewarding, showcasing K-Rino's prowess as one of the best MCs in the game. With more guest appearances than usual, No Mercy still feels very much like a K-Rino album—raw, thought-provoking, and essential for his fans.

Key Songs:

• No Mercy
• Ghetto Child
• By My Lonely
• Fallen Soldiers

31. Peanut Butter Wolf – My Vinyl Weighs a Ton (1999)

My Vinyl Weighs a Ton is a solid showcase of Peanut Butter Wolf's production, but in retrospect, it feels a little dated.

The album captures the essence of late-'90s underground hip-hop with its raw, boom-bap style, but it lacks the innovation that Stones Throw would later become known for. Despite this, it’s still a good listen, especially for fans of true-school hip-hop.

PBW’s production features strong turntablism moments, which elevate the album above the typical producer-featuring MC formula.

While it’s not one of Stones Throw's most groundbreaking releases, it holds its own and is definitely worth checking out for anyone curious about the label’s early days.

Key Songs:

• My Vinyl Weighs a Ton
• The Way I Feel
• Rhyme 'n' Reason
• Let’s Get It On

32. Koma – Le réveil (1999)

Koma's Le réveil stands as a prime example of thoughtful, socially conscious French rap. As a member of Scred Connexion, Koma’s solo album explores issues of identity, culture, and social justice.

Offering a perspective that stands apart from the braggadocious themes often found in American rap. The production is pure boom-bap, rooted in classic East Coast-style beats.

Koma’s flow is smooth but direct, and his lyrics resonate with depth and clarity, especially when dealing with issues of inequality and cultural exchange.

While the second half of the album may not be as strong as the first, Le réveil is a solid release and an essential listen for fans of French hip-hop and socially conscious rap.

Key Songs:

• La Rue
• Le Réveil
• Demain
• L'Arme Fatale

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33. Polyrhythm Addicts – Rhyme Related (1999)

One of the shortest yet strongest hip-hop albums of 1999, Rhyme Related packs a punch in just 35 minutes.

While brevity can sometimes feel like a missed opportunity for a longer, more complex album, this one benefits from its short runtime—there's no filler here, just hard beats and battle-style rapping.

The album is very much in line with the underground scene of the time, with DJ Spinna's production providing a steady, soulful backdrop for Shabaam Sahdeeq and other guest MCs.

Though it might not break new ground, Rhyme Related is a solid example of classic underground hip-hop and is especially appealing for those who like their rap raw, concise, and without the fluff.

Key Songs:

• Damn Right
• The Other Side
• For The People
• Drunk Dial

34. Eightball & M.J.G. – In Our Lifetime (1999)

After taking some time for solo projects, Eightball & MJG reunited for In Our Lifetime, one of their last great albums before they fell off with later releases.

While their sound has always been distinctly southern, this album does a great job of capturing their gritty street vibe while staying true to themselves.

The chemistry between the two is still there, and their authenticity shines through in every track. If you’re a fan of the group, this often-overlooked album is essential listening.

As it fits nicely alongside their earlier classics, offering the same raw energy and realness that made them legends in the South.

Key Songs:

• You Don't Want Drama
• In Our Lifetime
• Take A Trip
• The Game Belongs To Me

35. Public Enemy – There's a Poison Goin On.... (1999)

While Public Enemy’s 1999 release There’s a Poison Goin On.... doesn’t quite match the iconic status of It Takes A Nation of Millions, it is still a strong album in their late career.

The beats, produced by Tom E. Hawk, emulate the classic Bomb Squad sound while adapting to a more modern, refined style.

Chuck D’s political commentary remains razor-sharp, and his performance is as commanding as ever. The album stands as one of the better entries in their post-Apocalypse 91 discography.

Although it was initially sold online, it eventually found its way into physical stores, making it an underrated gem for Public Enemy fans.

Key Songs:

• Do You Wanna Go Our Way?
• Revolutionize
• Life’s A Bitch
• What Good Is A Bomb?

36. Kool Keith – Black Elvis / Lost in Space (1999)

This album marks the beginning of Kool Keith’s surreal and eccentric journey into the realm of Black Elvis. While it may not have the groundbreaking production of his earlier works, Black Elvis / Lost in Space solidifies Keith’s place as one of the most unique and quotable figures in hip-hop.

His flows are captivating, and his lyrics, as always, are absurd, hilarious, and bizarre. Tracks like “Livin’ Astro” showcase his boundary-pushing creativity.

The production here might be unorthodox for some, but it suits the eccentricity of Keith’s style. If you're a fan of Kool Keith’s off-kilter approach to rap, this is a must-listen.

Key Songs:

• Livin' Astro
• I'll Be Dat
• The Bandit
• Supernova

37. Roots Manuva – Brand New Second Hand (1999)

Roots Manuva is one of the UK hip-hop scene’s most important figures, and Brand New Second Hand helped cement his place in the genre.

With a unique blend of Jamaican influences and a forward-thinking approach to production, this album stands out as one of the early examples of how UK artists were carving their own path while avoiding the pitfalls of simply imitating American rap.

Roots Manuva’s distinctive voice and flow make him a standout, and the album’s sound—robotic and future-forward—was ahead of its time.

While not as groundbreaking as his next release, Brand New Second Hand is still an important part of UK hip-hop history.

Key Songs:

• On My Radio
• Big Tings
• Duppy Man
• The Fear

38. Mac – World War III (1999)

World War III is arguably the best album to come out of No Limit's late-'90s era. It doesn’t stray too far from the label's signature southern, gangsta rap style, but everything on this album clicks.

Mac’s voice and flow are among the best of the No Limit roster, and the beats from Beats By the Pound are some of the most consistent and best-produced of the era.

Despite the 70-minute runtime, the album doesn’t lose its energy and stays focused on street narratives. While Mac never reached the fame of other No Limit artists like Mystikal or Silkk the Shocker, this album proves that he was one of the label’s most capable talents.

Key Songs:

• Look At All The Hoes
• Bad Boy
• Ghetto Child
• Don't Hate

Also Read: Best Common Songs –  The 20 Dopest Common Songs!

39. GZA/Genius – Beneath the Surface (1999)

After the monumental Liquid Swords, GZA’s Beneath the Surface may have seemed like a step down for some, but it’s still a solid album.

GZA’s sharp, intellectual lyricism remains intact, with his razor-sharp wordplay and introspective bars. The production is classic Wu-Tang grimy, with dark, hard-hitting beats that complement his intricate flows.

While not quite as iconic as his earlier work, Beneath the Surface holds up as a worthy addition to the Wu-Tang legacy. If you're a fan of GZA's work, it's well worth a listen, even though it doesn't reach the heights of Liquid Swords.

Key Songs:

• Shadowboxin'
• Publicity
• Liquid Swords
• Smash

40. New Flesh for Old – Equilibrium (1999)

Equilibrium is a standout in the UK hip-hop scene, not just for its distinctive sound but for its bold attempt to push hip-hop forward.

New Flesh for Old blends gritty production with unique MCing, drawing on influences from acts like Company Flow but maintaining their own voice.

Their style is mechanical yet futuristic, pushing boundaries and offering something fresh. The MCs’ varied flows make for an engaging listen, even if Toastie Taylor’s voice might not be for everyone.

This album is a great example of how UK hip-hop was beginning to differentiate itself from its American counterparts. Equilibrium is a strong, forward-thinking record that deserves more recognition, and it stands as one of the best UK hip-hop albums of 1999.

Key Songs:

• Equilibrium
• Cul-de-Sac
• The Last Day
• AlphaOmega

41. Da Grassroots – Passage Through Time (1999)

Da Grassroots, a three-man production crew from Canada, made a name for themselves by producing beats for numerous Canadian rappers of the late '90s.

Passage Through Time is a producer-focused album featuring a variety of guest MCs. The beats are classic mid-'90s East Coast style — solid, even if not the most original.

The rapping is decent but not particularly memorable, making this album more about the vibe of the production than the lyrical content. Despite not being groundbreaking, it’s a hidden gem for fans of Canadian hip-hop and worth discovering.

Key Songs

• The Approach
• Here We Go
• Suckas Need Bodyguards

42. Project Pat – Ghetty Green (1999)

Project Pat, a member of Three 6 Mafia, delivers a gritty, dark album filled with bumping beats and crunk vibes on Ghetty Green.

If you're looking for deep, introspective lyrics, this isn't the album for you. Instead, it’s all about the raw energy and aggressive beats that fans of Three 6 Mafia will enjoy.

Project Pat’s delivery is perfect for this style of music, and the beats are designed to make you vibe rather than reflect. If you're into Memphis rap and the darker side of the South, this one’s a must.

Key Songs

• Ghetty Green
• Sippin' on Some Syrup
• Don't Call Me No Mo

43. Le Puzzle – Puzzle (1999)

This album from French hip-hop group Le Puzzle is a standout in the French rap scene. Produced by DJ Logistik (known for his work with other French rap acts), Puzzle is a pure boom-bap album with hard-hitting beats that bring a distinct East Coast vibe.

The lyrics may be a bit standard, but the group’s delivery and the beats make up for it, offering an engaging listen for fans of classic hip-hop. Though not groundbreaking, it’s an album that deserves more attention.

Key Songs

• Puzzle
• Encore et Toujours
• Ce Monde

44. Company Flow – Little Johnny From the Hozpitul: Breaks and Instrumentals Vol. 1 (1999)

While Funcrusher Plus may be more well-known, Company Flow’s Little Johnny From the Hozpitul is an instrumental album that captures El-P’s signature distorted beats and dark soundscapes.

The album doesn’t have the same impact as their earlier work, but it’s still an essential listen for Co Flow fans.

The repetitive nature of the tracks may turn off some listeners, but the album works best as a cohesive experience that shows El-P’s evolution toward his later solo projects, like Cannibal Ox and his own solo work.

Key Songs

• Run the Line
• Stain
• Low

45. Rob Swift – The Ablist (1999)

The Ablist is a turntablist-centric hip-hop album where the scratching takes center stage. Rob Swift, a skilled turntablist, collaborates with several guest MCs but the focus remains on the art of turntablism.

It’s comparable to the X-ecutioners album X-pressions, with a similar emphasis on scratching, though Rob Swift’s beats are tighter and more focused.

At 48 minutes, the album doesn’t overstay its welcome, and while it may be a bit niche, it’s a fun and engaging listen for fans of turntablism.

Key Songs

• The Ablist Anthem
• Ablist
• Cutting Through the Noise

46. Missy Misdemeanor Elliott – Da Real World (1999)

Missy Elliott’s second album, Da Real World, marked a more consistent and refined sound, thanks to Timbaland’s production.

The synergy between Missy and Timbaland is on full display here, with innovative beats that blend hip-hop and R&B.

Though Missy’s persona may not be for everyone, the album’s creativity and Timbaland’s genre-defying beats make this an influential mainstream album from 1999. Guest appearances from Eminem, Big Boi, and Redman add to the album’s appeal.

Key Songs

• She's a Bitch
• All in My Grill
• Hot Boyz

47. Koopsta Knicca – Da Devil's Playground: Underground Solo (1999)

Koopsta Knicca's Da Devil's Playground: Underground Solo is one of the darkest and slowest entries in the Three 6 Mafia camp.

The album is drenched in a haunting, chopped and screwed atmosphere that brings to mind DJ Screw’s style, with beats that slow down the pace to an almost hypnotic degree.

While Koopsta’s lyrics are nothing groundbreaking, the album's vibe is undeniably immersive. It’s not about lyrical depth here but about the sinister mood and the unique Memphis sound. If you’re a fan of the darker, slower side of hip-hop, this one’s definitely worth checking out.

Key Songs

• The Devil's Playground
• Die N***a Die
• R.I.P.

Also Read: The Top 25 Best Nas Songs of All Time!

48. Various Artists – Subtext (1999)

Subtext is an often-overlooked compilation album from Strength Magazine, showcasing the best of the West Coast underground scene at the time.

Featuring a mix of Stones Throw artists and other underground talents, this album offers a collection of exclusive tracks that represent the diversity and creativity of the era.

One of the highlights is the production of Madlib, who handles all the interludes with his signature sound. The album’s vibe is deep, experimental, and undeniably cool, making it a hidden gem worth discovering for fans of West Coast underground hip-hop.

Key Songs

• Madlib's Interludes
• Smoke Break
• This Ain't No Joke

49. Tash – Rap Life (1999)

Tash’s Rap Life is a solid offering from the former Tha Alkaholiks member. While not as strong as previous albums from Tha Liks, this one still shows off Tash's talent and knack for entertaining lyricism.

The album features a mix of East Coast and West Coast beats, giving it a diverse sound while maintaining cohesion throughout.

Tash’s witty, humorous rhymes add an enjoyable element to the album, making it a fun listen for fans of West Coast hip-hop. Despite not being perfect, it’s a great album for those who enjoy his style or are fans of the Liks.

Key Songs

• Big Girls
• Rap Life
• Where's the Weed?

50. La Malédiction du Nord – Les raisons de la colère (1998)s

This album from French rap group La Malédiction du Nord is a solid piece of boom-bap hip-hop, blending East Coast influences with sharp, hard-hitting beats.

Though the production style might be somewhat formulaic, the group still delivers with compelling lyrics and a raw, "hard" rap style.

The album’s strengths lie in its intelligent lyricism and the group’s ability to maintain a cohesive sound. For fans of French hip-hop or boom-bap enthusiasts, this album is a great addition to your collection, even if it doesn’t reinvent the wheel.

Key Songs

• Les Raisons de la Colère
• L'Injustice
• La Règle du Jeu