1. Mos Def - Black On Both Sides

Mos Def’s masterpiece. Mos Def is one of the most underappreciated emcees out there – but he has a unique voice and his flow is tight. He’s intelligent, humorous, passionate, creative, and socially conscious. Black On Both Sides is a must-have for any and all Hip Hop fans.

Top tracks: Mathematics | Ms. Fat Booty | Brooklyn | Hip Hop

2. The Roots - Things Fall Apart

With Questlove’s perfect instrumentals and Black Thought’s thoughtful, socially conscious rhymes (not to mention his exceptional emcee skills), Things Fall Apart is yet another excellent The Roots album, their fourth. With additional rhyming from Malik B, Dice Raw, and guests like Common and Mos Def, you know you can’t go wrong with this The Roots classic.

Top tracks: The Next Movement | You Got Me | Double Trouble | Act Too (The Love of My Life)

3. MF DOOM - Operation Doomsday (1999)

What a comeback! After a long hiatus following his brother’s death and the end of KMD, Zev Lov X reinvented himself and came back on the Hip Hop scene as MF DOOM. He would go on to release a myriad of excellent albums and collaborations – and Doomsday is up there with the best of his work.

Top tracks: Doomsday | Rhymes Like Dimes | Hey! | Gas Drawls

4. Eminem – The Slim Shady LP

Eminem‘s sophomore album, and major-label debut, was a game-changer. The real start of an epic career that would make Em a worldwide phenomenon and one of the best-selling artists in music ever.

Top tracks: My Name Is | As The World Turns | Rock Bottom | 97 Bonnie & Clyde

5. Pharoahe Monche – Internal Affairs

Internal Affairs is the solo debut from former Organized Konfusion member and brilliant lyricist Pharoahe Monch. After three acclaimed albums with Prince Po as Organized Konfusion, Pharoahe went for a harder sound on his first solo outing. High energy and consistently good, this album may not be the ultimate classic some of us expected after his work on the O.K. albums, but it is a banger nonetheless.

Top tracks: Simon Says | The Truth | The Light | Rape

6. Dr Dre – 2001

An excellent follow-up to Dr. Dre’s epic classic The Chronic. Not quite as revolutionary as The Chronic was – but a definitive reaffirmation that Dre still was the West’s top-producer, even after a seven-year hiatus between albums (under his own name that is – of course he produced a whole lot of classic music for others in the meantime).

Whereas The Chronic changed the face of (West Coast) Hip Hop, with 2001 Dr. Dre just holds it down. Confident, superior production – the only criticism could be that the album contains a few misses (“Let’s Get High” most notably) and that it could have done without the pointless skits. Other than that: 2001 simply is another Dr. Dre classic.

Top tracks: Forgot About Dre | Still D.R.E. | What’s The Difference | The Next Episode

7. Dr. Dooom - First Come, First Served

This album is up there with Dr. Octagonecologyst and Sex Style as one of Kool Keith’s best solo albums. The album begins with Kool Keith’s new alter-ego Dr. Dooom killing the Dr. Octagon persona. Lyrically he is in top form here: flow and delivery are excellent and the lyrics are wonderfully and characteristically bizarre. Gotta love that No Limit parody cover too.

Top tracks: No Chorus | I Run Rap | Apartment 223 | Neighbors Next Door

8. Blackalicious – Nia

The Sacramento-based duo consisting of producer/DJ Chief Xcel and lyricist The Gift of Gab drops an excellent debut album with Nia. Progressive, soulful, stylistic, and inventive production and exceptional lyricism by Gift Of Gab, truly one of the most underrated and poetic emcees in the Hip Hop game. Nia is a gem.

Top tracks: Deception | Smithzonian Institute of Rhyme | If I May | Shallow Days

9. Prince Paul – A Prince Among Thieves

Producer extraordinaire Prince Paul (Stetsasonic, De La Soul, Gravediggaz) comes with his second solo album – the brilliant concept album A Prince Among Thieves, sometimes dubbed the first ‘rap opera’. The album tells the story of a young guy named Tariq, who is trying to get a record contract and needs to make some money to finish up his tracks and get his demo tape ready for a meeting with Wu-Tang Clan’s The RZA.

A Prince Among Thieves features cameos by Kool Keith, Big Daddy Kane, Chubb Rock, Biz Markie, De La Soul, Everlast, Sadat X, Xzibit, Kid Creole, Special Ed, Chris Rock, RZA, and Buckshot. Fresh beats and dope rhymes throughout – without a doubt, this is one of the best concept albums in Hip Hop ever.

Top tracks: Macula’s Theory | More Than U Know | Handle Your Time Weapon World

10. Lootpack – Soundpieces: Da Antidote

Lootpack is a trio consisting of Madlib, Wildchild, and DJ Romes, signed to Stones Throw Records at that time. Soundpieces: Da Antidote is their debut, and it is now recognized as an underground classic. The album especially shines because of the wonderfully inventive and creative board work by Madlib, and also because of the point Lootpack tries to make – to be the real Hip Hop alternative to the materialism and violence in the dumbed-down mainstream rap.

Top tracks: Questions | Frenz Vs Endz | The Anthem | Episodes

11. Method Man & Redman - Blackout!

Blackout! is the first collaborative album by Method Man and Redman, capitalizing on the great synergy they proved to have during earlier collaborations. Nothing surprising or substantial here: just great fun, wit, and wordplay by two great stoner emcees who complement each other styles perfectly.

Top tracks: Da Rockwilder | 1,2,1,2 | Cereal Killer | 4 Seasons

12. Handsome B-boy Modelling School – So How’s Your Girl

Handsome Boy Modeling School was a collaboration between renowned producers Dan The Automator (Gorillaz, Dr. Octagon, Deltron 3030) and Prince Paul (Stetsasonic, De La Soul, Gravediggaz, A Prince Among Thieves), which produced two dope albums, most notably this experimental masterpiece, the first of the two HBMS albums. This clever and humorous album is one of 1999’s hidden gems.

Top tracks: Magnetizing | Once Again (Here to Kick One for You) | Waterworld | Holy Calamity (Bear Witnesss II)

13. Jeru The Damaja - Heroz4Hire

Heroz4Hire is the third album by Jeru the Damaja. It was entirely produced by Jeru the Damaja himself, unlike his first two albums which were produced by DJ Premier. Lacking Premier’s magic touch may have hurt the album publicity-wise, but Jeru has done an admirable job on the production side.

Jeru’s production is innovative and raw and his lyrics are clever and thought-provoking as always. Jeru represents true Hip Hop at its rawest and this album is more than a worthy part of his catalog. Even though this album almost never gets mentioned, and not nearly as much as Jeru’s first two, it’s just about as good – and underrated for sure.

Top tracks: Bitchez Wit Dikz | Verbal Battle | Presha | 99,9%

14. Rubberoom - Architechnology

With its full-length debut Architechnology, this crew known as Rubberoom emerged from the depths of the Chicago Hip Hop underground. Progressive production unit The Opus (Isle Of weight, Fanum, and DJ Stizo, plus over a dozen of the Windy City’s most talented turntablists) crafted well over an hour of ominous soundscapes for emcee Lumba and Meta-Mo to spit their abrasive bars over – the intensity of the lyrics and music combined is insane.

“Smoke”, “Lockjaw”, “The Shining”, “Bleach”, “Acid”, “Sector Rush (Re-Built)”, “Architechnology Nine”, “Trail Of The Vampire”, “Style Wars”  – nothing but gothic bangers on Architechnology. This is one of the most slept-on albums of the 1990s, even in the underground.

15. Inspectah Deck - Uncontrolled Substance

Underrated or overrated? Opinions are divided on this one. Originally planned for a 1995 release, along with the rest of the first wave Wu solo albums, all the instrumentals made by the RZA for Deck’s intended debut were destroyed in a flood at RZA’s house. It is said that the delay hurt Deck, both because the new beats (only 2 by RZA) were not as good as they could/might have been and because he did not benefit from the momentum the first Wu solo albums got.

Whatever the case, Inspectah Deck still comes correct on this album. Admittedly, the beats could have been better here and there, but lyrically Deck is on point as always – so this album is better as some say. Still, one wonders what would have happened if those original RZA beats hadn’t been lost and Deck would have debuted in 1995 too…

Top tracks: Movas & Shakers | Word On The Street | Show N Prove | Longevity

16. Kurupt - Tha Streetz Iz A Mutha

Kurupt’s second and best solo album. The subject matter is typical nineties g-funk/gangsta sh*t, but the production on this album is on point, and Kurupt is a better rapper than most. A must-have for fans of that original West Coast g-funk gangsta rap.

Top tracks: I Call Shots | Girls All Pause | Live On The Mic | Represent Dat G.C.

17. Missy Elliott - Da Real World

Da Real World, Missy Elliott’s second album, is probably the most divisive in her entire catalog. Some people knock it for being ‘too dark’ or for being boring even, others hail it as Missy’s a top-three Missy album. We belong to the latter group. We think this album contains some of the best instrumentals Timbaland ever crafted for Missy, and we like the darker vibes, plus the fact Hip Hop sensibilities don’t take too much of a backseat to Timbaland’s R&B and dance sounds. “She’s a Bitch” is the obvious highlight on Da Real World, but there’s plenty more to enjoy: “Beat Biters”, “All N My Grill”, and “Stickin’ Chickens” just a few of the great tracks on display here. For us Da Real World is underappreciated in Missy’s catalog, we think it is one of her best albums.

Top tracks: She’s a Bitch | Beat Biters | All N My Grill | Stickin’ Chickens

18. Nas - I Am...

One of two 1999 releases from Nas, and the best of the two. Even so, I Am… is a bit of a mixed bag. It contains some of Nas’ best tracks – such as the DJ Premier-produced masterpiece “Nas Is Like” – but also some misses. Nas’s problem never was his lyrics nor his mic skills – he is and will always be one of the best, most complete emcees in the game – but his beat selection. Not a bad album at all (as some would have you believe), but from Nas, we just expect more…

Top tracks: Nas Is Like | NY State Of Mind Pt 2 | Ghetto Prisoners | Undying Love

19. Q-Tip - Amplified

Amplified is Q-Tip’s much-maligned debut solo-album. Sure, it’s not a Tribe album, the lyrics are not very meaningful and Q-Tip is clearly going for a more commercial sound than we all might have wanted – but what Ampiflied does, it does well.

The album was mostly produced by Q-Tip himself and J-Dilla, so quality ensured. Despite the lack of lyrical substance, Amplified is an enjoyable enough listening experience – mainly because of the dope beats throughout. Just don’t expect a Tribe album and enjoy this for it is: a lightweight but fun listen.

Top tracks: Vivrant Thing | Breathe And Stop | Things We Do | Let’s Ride

20. Slick Rick - The Art Of Storytelling

A non-fatal self-defense shooting (in which a bystander got hit too) and trouble with US immigration services landed the England-born Slick Rick in prison, just when he was getting ready to capitalize on the success of his landmark 1988 solo debut Great Adventures of Slick Rick. His legal woes were the cause he could never fully dedicate his artistic abilities to creating another classic, but this album – his fourth and final one – was somewhat of a return to form.

Top tracks: Street Talkin | Memories | Impress The Kid | I Run This

21. Deep Puddle Dynamics - The Taste of Rain...Why Kneel

The Taste of Rain… Why Kneel is the only studio album by Deep Puddle Dynamics, a collaboration between Sole, Doseone, Alias, and Atmosphere‘s Slug – this is one of the best albums released on Los Angeles-based avant-garde record label Anticon.

22. DMX – …And Then There Was X

…And Then There Was X is DMX’s third studio album, released on December 21, 1999, by Ruff Ryders Entertainment and Def Jam Recordings. The album was certified 5x Multi-Platinum by the RIAA on February 7, 2001 – making it DMX’s best-selling album to date. ..And Then There Was X debuted at number one on the Billboard 200, making it his third album in a row to debut at the top. With two multi-platinum albums in 1988, that year will always be DMX’s most memorable one, but in 1999 he was still on his winning streak – ...And Then There Was X is the third act in an incredibly impactful one-two-three punch.

“What’s My Name”, the anthemic “Party Up (Up in Here)”  (the most successful single of his career), and “What These Bitches Want” are the eye-catching singles on …And Then There Was X, but the whole album bangs. The lyrics, the delivery, the flow, the hooks, the beats – everything on this album was on point, and almost as strong as the two albums preceding it. …And Then There Was X still is peak DMX.

23. Ice T – 7th Deadly Sin

Although it didn’t get the recognition it deserved, this Ice-T album actually is pretty good – not better than his first four albums, but arguably his best album since his magnum opus Original Gangster (1991). 7th Deadly Sin is an underrated album by one of Hip Hop’s biggest icons.

Top tracks: Retaliation | Common Sense | Check Your Game | Valuable Game

24. The High & Mighty - Home Field Advantage

The High & Mighty are emcee Eon and producer Mighty Mi, who drop a light-hearted and laid-back album with this debut album, released on Rawkus Records. Some dope guest spots from Mos Def, Mad Skillz, Cage, Pharaohe Monch, and Eminem ensure this is a quality Hip Hop album.

Top tracks: Hot Spittable | B-Boy Document 99 | Dirty Decibels | Top Prospects

25. Peanut Butter Wolf - My Vinyl Weighs A Ton

Stones Throw Records founder Peanut Butter Wolf dropped a wonderful album with My Vinyl Weighs A Ton. Great turntablism and great lyricism from a bunch of Stones Throw talent (Rasco, Planet Asia, The Lootpack, and others) over vibrant soundscapes cooked up by Peanut Butter Wolf himself – this is a dope album.

Top tracks: Tale of Five Cities | Casio | Styles, Crew, Flows, Beats | Run The Line

26. Public Enemy - There's A Poison Goin' On

Public Enemy sort of lost their momentum after their first four brilliant albums, two of which – Nation of Millions and Fear Of A Black Planet –  are all-time classic masterpieces. This is their seventh album and it is underrated as hell. In an era in which materialistic and violent Hip Hop had long won the mainstream spotlight in favor of conscious Hip Hop, Chuck D and Public Enemy kept doing their thing: dropping knowledge on us.

Public Enemy became the first platinum-selling group to release a new album through the internet, in order to bypass the established record-label power structure through the use of new technology. Public Enemy’s disenchantment with Def Jam and the record industry in general is one of this album’s major themes.

Top tracks: Do You Wanna Go Our Way??? | LSD | Crayola | Last Mass Of The Caballeros

27. Rakim - The Master

The Master is the second solo album by Rakim, the follow-up to his debut solo album, The 18th Letter (1997). This album would be Rakim‘s last studio album for nearly a decade, until 2009’s The Seventh Seal. The Master suffered a bit from the same problem its predecessor had: Rakim’s masterful rhyming does not always fit the beats, which are a mixed bag again. Although Rakim never recaptured the magic he created on the Eric B & Rakim albums, this is not a bad album at all, and a must-have for Rakim fans at the very least.

Top tracks: When I Be On The Mic | Finest Ones | Strong Island | Flow Forever

28. Mobb Deep - Murda Muzik

Because of excessive bootlegging, the version of Murda Muzik that was finally released was different than the originally intended one, but it turned out to be an excellent Mobb Deep album anyway. Slightly less acclaimed than The Infamous and Hell On Earth, it did become their biggest commercial success, reaching platinum status eventually. The last great Mobb Deep album (although 2014’s The Infamous Mobb Deep was a return to form).

Top tracks: Quiet Storm | The Realest | Streets Raised Me | Murda Muzik

29. Jay-Z Vol. 3... Life and Times of S. Carter

Not his best, not his worst. Jay-Z’s fourth album in as many years does the previous two did: giving us dope Jay-Z rhymes over dope beats here and some pop tunes there. Jay-Z rhyming is as good as ever, but the beats are not all great and not all guest spots are up to par (Amil, most notably, is not very good). This album is not in the league of his classic debut Reasonable Doubt or the classic album he would drop in 2001 – The Blueprint – but it’s a perfectly fine Jay-Z album as it is.

Top tracks: Big Pimpin’ | Watch Me | There’s Been A Murder | So Ghetto

30. Kool Keith - Black Elvis / Lost In Space

Kool Keith’s second 1999 album. This is one of his most easily accessible albums and that may be the reason it misses a bit of the spark that raises albums like this year’s First Come First Served and earlier efforts like Sex Style and Dr Octagonecologyst to a higher level. That said:  Black Elvis / Lost in Space is a dope album anyway, as always filled with weird choruses, Kool Keith’s bizarre lyrics, and his unique sense of humor.

Top tracks: Supergalactic Lover | Rockets On The Battlefield | Livin’ Astro | Maxi Curls

31. GZA/Genius - Beneath The Surface

GZA’s third solo album (and his second one after the formation of the Wu-Tang Clan) is one to forever polarize opinions – some hate it, some love it. Because of the fact that the second wave of Wu-Tang solo albums were not all as good as their predecessors (especially the 1999 albums from Raekwon and Ol’Dirty Bastard disappointed badly), that does not mean they were all bad. Beneath The Surface is one of the better ones.

As always, GZA shines with his thought-provoking metaphors and outstanding delivery – it can even be argued he even outdoes himself here lyrically compared to his magnum opus Liquid Swords. Sure, the beats could have been better here and there, but this album on the whole is much better than some haters would have you believe.

Top tracks: Breaker, Breaker | Publicity | Hip Hop Fury | Mic Trippin

32. Eightball & M.J.G. - In Our Lifetime

In Our Lifetime is the fourth studio album from Memphis legends Eightball & M.J.G. Not their best, but not their worst either. Full of laid-back Dirty South beats, with guest appearances from the likes of OutKast and Cee-Lo Green – so you know all ingredients are there for another solid Eightball & M.J.G. record.

Top tracks: Do It How It Go | Daylight | Paid Dues | Throw Your Hands Up

33. Tech N9ne - The Calm Before The Storm

The Calm Before the Storm is the debut album by rapper/actor Tech N9ne, the first in a long line of pretty dope albums. With his hardcore lyrics and crazy fast-and-slow flow he never really got mainstream recognition – but he created a nice little niche for himself in the Hip Hop game, which gave him a loyal worldwide fanbase. The Calm Before The Storm – a Mid-West album with clear G-funk and Dirty South influences beat-wise – is a bit overlooked within Tech N9ne’s discography, but for us, it is one of his best.

Top tracks: Cotton Soldier | Bitch Sickness | Mitchell Bade | Relish

34. EPMD - Out Of Business

Out of Business is the sixth album from EPMD. Definitely not as good and consistent as their first four, but a sub-par EPMD album is still better than most other albums released in any given year. Some weaker moments on this album, but some classic EPMD joints as well – you really can not go wrong with Erick and Parrish, one of the best duos in Hip Hop.

Top tracks: You Got Shot | Right Now | Symphony 2000 | Jane 6

35. The Beatnuts - A Musical Massacre

Not the Beatnuts’ best album, but it is hard not to love those guys and their music. This album is worth the price admission solely on the strength of the epic single “Watch Out Now” – and even though A Musical Massacre may not be as consistent as some of their other albums, there is plenty more to enjoy here.

Top tracks: Watch Out Now | Turn It Out | Look Around | Slam Pit

36. Atmosphere - Headshotz Se7en

Released on cassette only in 1999 (a CD with bonus material was released in 2005), this second Atmosphere album is a transformative/transitional one – from the witty lyricism on 1997’s Overcast! to the deeper content Atmosphere would become famous for later on. It is both on display here, and even though the album (cassette…) might have been even better if it had been a bit shorter and sonically more polished, this still is classic Atmosphere.

Top tracks: The Jackpot / Swept Away | The Stick Up | Heart | Molly Cool

37. K-Rino - No Mercy

K-Rino’s fourth album, and of the best in his incredibly extensive catalog. Don’t sleep on Houston legend K-Rino.

Top tracks: No Mercy | Trust No One | Lords of The World | Feel Me Flow

38. Scaramanga - Seven Eyes, Seven Horns

Scaramanga a.k.a. Sir Menelik biggest claim to fame up till the release of this album was his contribution to Kool Keith’s classic Dr. Octagonecologyst. With Seven Eyes, Seven Horns he drops a wonderfully obscure album himself, with dope rhymes and beats.

Top tracks: Holding New Cards | Seven Eyes, Seven Horns | Star Of The Empire | Shallah Magnetic

39. Black Moon - War Zone

Black Moon’s sophomore album is not quite the classic their debut Enta Da Stage was, but there’s still enough to appreciate here. With Buckshot taking point and 5Ft complementing his flow, you know lyrically the bases are covered (even though the ‘tough guy/gun talk’ subject matter does get a bit trite at times). With Evil Dee and The Beatminerz on the production, the beats are typically NYC noir. Nothing really wrong with War Zone, it just could and should have been somewhat tighter, with a bit more energy and focus – the things that made Enta Da Stage the classic that it is.

Top tracks: War Zone | Annihilation |  Two Turntables & A Mic | Whirlwind

40. Hot Boys - Guerrilla Warfare

A continuation of the sounds of Juvenile’s 400 Degreez, this second Hot Boys album is included in this list on the strength of the dopeness of Mannie Fresh’s production. The lyrics are kinda dumb, but the beats are fire. A Southern classic.

Top tracks: We On Fire | Ridin | Tuesday & Thursday | Too Hot

Honorable Mentions

• Snoop Dogg – No Limit Top Dogg
• Warren G – I Want It All
• Souls of Mischief – Focus
• U-God – Golden Arms Redemption
• The Notorious B.I.G. – Born Again
• Nas – Nastradamus
• Arsonists – As The World Burns
• Eve – (Let There Be Eve….) Ruff Ryders First Lady
• Polyrhythm Addicts – Rhyme Related
• Busdriver – Memoirs Of The Elephant Man
• O.G.C. – The M-Pire Shrikez Back
• Swollen Members – Balance
• Buckshot – The BDI Thug
• Rob Swift – The Ablist
• Ja Rule – Venni Vetti Vecci
• Tash – Rap Life
• Defari – Focused Daily
• Saukrates – The Underground Tapes
• Andre Nickatina – Tears Of A Clown
• Esham – Mail Dominance
• Natas – Wicket World Wide.Com
• Mac Dre – Rapper Gone Bad
• Cool Breeze – East Point’s Greatest Hit
• Juvenile – Tha G-Code
• B.G. – Chopper City In The Ghetto
• Koopsta Knicca – Da Devil’s Playground: Underground Solo
• E-40 – Charlie Hustle: Blueprint Of A Self-Made Millionaire
• Various Artists – Rawkus Presents: Soundbombing II