Independent As Fuck 3: 32 Essential Underground Hip Hop Releases From 1999

16 min readDec 19, 2019


After the Jiggy Era took over the mainstream Rap world and commercial radio, the kind of Rap that once thrived on major labels was progressively forced underground like the Morlocks. What happened next was the formation of a Resistance forced to eek out spaces in the shadow of the First Order.

This 3 part series was created to acknowledge the essential, classic & often times slept on, overlooked, obscure, independent underground Rap EP’s & LP’s, mixtapes, scratch albums, instrumental projects or compilations. SIDEBAR: I fought for the Resistance, thus this story is told from my perspective. Time to conclude the trilogy.


1999 should’ve signified that we were clearly into a brand new era following a short transition period after the close of the 2nd Golden Era which spanned from 1992 to 1996. Thing is, it was part of a new era… just not a golden one, a divergent one. I consider 1997–2002 to be something called the Backpack/Underground Era which existed simultaneously as the Jiggy Era, this odd occurrence made possible by the Rap Apartheid/Jim Crow system that had been in existence since 1997. By 1999, the growing divide had transformed into a chasm and after this year was over? Never the twain would meet again…

Think of the mainstream Rap and the independent/underground Rap industries kind of like Earth 1 & Earth 2 from DC Comics. I’m going to highlight 32 essential indie/underground Hip Hop projects in 1999 that further defined this divide and influenced an entire generation of artists, emcee, producers, turntablists and fans/listeners alike who followed.

1999 was analogous to 1988 and 1994 in the sense it was the third year of a firmly established new era that lent itself to significant growth within the space. Before I began writing about this time period back in 2006, few initially considered 1997–2002 to be a divergent era in Rap music. After I spent years breaking down every imaginable aspect of this time period it became pretty clear to me that a) my work seemed to finally resonate with readers and b) no else cared to do the work I was doing so I was essentially in this space alone breaking down the timeline.

Since 1986 contained the initial seminal releases of a new era it didn’t contain as many key releases as the following year (1987). 1997 didn’t have as many essential indie/underground releases as 1998 did due to progression and the growth/evolution of the space within the confines of that divergent era as highlighted by the fact I listed 20 projects for 1997 versus 25 for 1998 in previous editions.

For that reason, we’ll finish off this series highlighting 32 seminal/essential/classic Hip Hop/Rap projects in this list spanning the 52 weeks of 1999. Due to the odd nature of projects being re-released months later under another distributor (international vs. North American) or being available through different methods/outlets before finding wider distribution stateside leading to them finally getting write ups in various publications before they spread it’s made nailing down exact release dates hard.

Even worse? Some of these albums were pushed back from the dates listed in their original promo copy or in CMJ New Music Report so I just posted every date I saw because oftentimes with indie Rap albums it was often months before we finally realized they were even out. Why lie? Let’s begin:

Peanut Butter WolfMy Vinyl Weighs A Ton [Stones Throw/Copasetik](January 19th, 1999)

I bought this Stones Throw compilation from my old job when I was the senior 1st floor manager at Tower Records. We had Newbury Comics down the street from us, further down on Newbury there was CD Spins. On the next block there was Mystery Train. Directly across the street on Mass. Ave was Biscuithead Records and on the next block on Boylston St. was Looney Tunes. The UGHH store was close nearby on Huntington and Nuggets was a few blocks away on Comm. Ave in Kenmore Square. This was the greatest time to be an underground Rap fan in the Metro Boston Area.

Black Moon— War Zone [Duck Down](February 23rd, 1999)

The return of Black Moon was one of the biggest stories of 1999. Duck Down had remained a force throughout the decade and its core groups were releasing their sophomore albums. Black Moon’s “War Zone” was the crown jewel of that wave. As soon as we heard “Onslaught” begin playing we knew what we were getting.

Rob Swift— The Ablist [Asphodel](February 23rd, 1999)

Rob Swift’s follow up to his classic debut turntablism album was defined by his creedo, “the will to do different shit”. Rob experimented with the craft and helped to stretch the boundaries of the artform. I thoroughly enjoyed “I’m Leaving” with his homie Gudtyme and the Genghis Khan phoned in verses that predated Hell Rell’s and Shyne’s. A must own 1999 project for any reputable Hip Hop fan.

Rubberoom— Architechnology [Indus/3–2–1/Zero Hour] (March 2nd, 1999)

Chicago’s Rubberoom boasted 13 turntablists doing the scratches on this project. Easily one of the most slept on and overlooked classic Rap releases from 1999 on Fiona Bloom’s 3–2–1 Records who had Big Juss as an A&R. They appeared in the equally obscure Staticopy Imagery’s “Open Transport” documentary on VHS. Only the true underground heads were up on this album, I even have the “Sector Rush” CD single.

Superrappin’: The Album [Groove Attack](March 23rd, 1999)

Groove Attack was a European label/distributor so I saw ads for this upcoming project and the singles in all the UK & European Hip Hop publications and graffiti magazines for months on end. Once the CD dropped it was available via every international Hip Hop mailorder catalog in addition to Fat Beats, UGHH, Sandbox Automatic, HipHopSite, etc. This compilation was everywhere if you were an active head.

J-Zone — Music For Tu Madre [Old Maid](April 6th, 1999)

J-Zone’s album spread via word of mouth. I can’t tell you how many J-Zone lines I heard quoted at the most random times and it would lead to someone having to play the particular song. Then there were the beats… Needless to say, J-Zone became a favorite. You could tell he was a fan & a student of music while simultaneously understanding when & where tradition was stifling.

J-Zone’s music required you to be open minded as opposed to thinking there’s only one way for “underground” or “real Hip Hop” to sound. Brings me back to listening to his songs on RealPlayer clips via a 33.6K US Robotics modem dreaming of being able to cop a 56K modem soon.

Ugly DucklingFresh Mode EP [1500](April 6th/20th, 1999)

I remember seeing Ugly Duckling get mentioned in CMJ New Music, Blaze, The Source and XXL for “Fresh Mode” and deciding to track down the EP for myself. The EP made a significant amount of noise thanks to tracks like “Get On This”, “Now Who’s Laughin’” and “Everybody Come On”. Due to advance copies and conflicting information I’ve seen in several publications I can’t nail down an exact release date.

DJ Spinna— The Beyond Real Experience [Beyond Real](April 13th, 1999)

DJ Spinna is easily one of the MVP’s of this entire era in terms of being a DJ, producer, label head, A&R and an advocate for great music period. The countless classics crafted in his legendary Thingamajig Lab with Joc Max & Ge-ology. This compilation included contributions from Jigmastas, I.G. Off & Hazadous, Basement Khemists, Dynas, Old World Disorder, Ha The Jet Black & Mr. Akil and features from Pharoahe Monch, Talib Kweli, Shabaam Sahdeeq & Mr. Complex. Another essential underground Rap release from 1999.

BlackaliciousA2G EP [Quannum/3–2–1](April 20th, 1999)

Blackalicious’ “A2G EP” contains “Alphabet Aerobics” which not only was a big record in underground Rap circles stateside but apparently blew up in the UK. Months later Blackalicious’ LP “Nia” was released in Europe but wouldn’t drop in North America until 2000 but that is another story…

M-Boogie — Laid In Full [Blackberry](May 4th, 1999)

M-Boogie released a massive West Coast centric underground Rap compilation featuring luminaries such as Kut Masta Kurt, Planet Asia, DJ Babu, Rhettmatic, Lootpack, The Associates, Rasco, Insane Poetry and Masters Of Illusion. This was a really strong year for underound Rap compilations.

Soundbombing 2 [Rawkus](May 18th, 1999)

I actually wrote about this album for an outlet that paid me to do it. No surprise it’s on this list today.

Swollen MembersBalance [Battle Axe](June 1st, 1999)

Swollen Members 12' singles on vinyl between 1997 and 1999 were must haves based on the guest appearances and producers alone but their LP “Balance” contained many of them. “S&M On The Rocks”, “Committed”, “Left Field”, “Front Street”, “Counter Parts”, “Strength”, “Out Of Range”, “Bless & Destroy” & “Bottle Rocket” were all included plus the beats were handled by The Alchemist, Evidence, Zodak, Kemo, Paul Mice, Del, Joey Chavez & Kool DJ E.Q..

Also… the woman in the “Lady Venom” video was on the NBC Saturday morning TNBC show “Just Deal” in 2000–02. I’m like IMDb for Canadian actresses… I blame CableVision carrying MuchMusic between 1994 and 2003 for that. Swollen Members are Canadians. Like Obscure Disorder. And Mood Ruff. And Shades Of Culture. And Brassmunk. And Rascalz. And Tara Chase. And Mathematik. And Frankenstein. And Ghetto Concept. And Arcee. And…

Polyrhythm AddictsRhyme Related [Wreck/Nervous](June 8th, 1999)

Polyrhythm Addicts’ “Not Your Ordinary” was the lead single of Nervous’ “Hip Hop Independents Day” compilation from 1998 and the one that generated the most excitement and buzz. The supergroup of DJ Spinna, Mr. Complex, Shabaam Sahdeeq & Apani B. alone screamed album in the context of this era of underground Rap so here we are.

DJ SpinnaHeavy Beats Vol. 1 [Rawkus](June 15th, 1999)

DJ Spinna had releases on consecutive weeks on different labels in 1999 if you want any further proof he was one of the MVP’s of underground Rap between 1997 and 2002. I actually asked him about this back in 2013 at a RBMA session in Harvard’s Hip Hop Archive. Rawkus was adept in marketing their Rap albums & compilations but the instrumental releases they dropped in June 1999 didn’t get the “Soundbombing 2” treatment.

I’ll never forget first hearing “Watch Dees” featuring Eminem and Thirstin Howl III, “Who U Be” featuring Missin’ Linx and “Time Zone” featuring Apani B. and Talib Kweli. B-Boys & B-Girls used to regularly dance and practice to “A Grooveamungus” and “Rock” as well.

Company Flow— Little Johnny From The Hospitul [Rawkus] (June 22nd, 1999)

There were promotional postcards made for these two Rawkus releases. “Little Johnny From The Hospitul” wasn’t a sophomore album as Mr. Len and Bigg Juss had each struck out on their own and Company Flow wasn’t up to giving Rawkus another album.

I remember that on June 24th, 1999 there was a dual release party for “Little Johnny From The Hospitul” and Mr. Lif’s “Triangular Warfare” 12" on Brick at the Middle East. Company Flow (El-P & Mr. Len), Jedi Mind Tricks, Mr. Lif, Skitzofreniks & DJ 7L were on the bill for only $12 ($18.50 in 2020 money). The final Company Flow singles would end up “End To End Burners” and “Patriotism”. Next phase? Enter Def Jux.

Lootpack Soundpieces: Da Antidote [Stones Throw](June 29th, 1999)

This album is the textbook definition of a classic underground Rap album that was completely overlooked by anyone that wasn’t a head. It dropped around the same time as Ja Rule’s debut on Def Jam, Missy “Misdemeanor” Elliott’s sophomore album and GZA’s “Beneath The Surface” on MCA, meaning the mainstream Rap audience was paying it absolutely no attention.

The Hard Knock Life Tour ran across North America between March 2nd and May 2nd, 1999 so every team was selling and pushing the next product to piggyback off of Def Jam’s success. That big venue tour generating a disgusting amount of revenue while going off without a hitch created a great deal of opportunity within the space of the Rap industry. This meant very little attention was paid to this brilliant ass album on Stones Throw with no star that could appear on MTV’s TRL on it.

Quannum— Spectrum [Quannum](July 13th/27th, 1999)

Quannum, formerly known as Solesides was crucial to the beginnings of the era. The releases that kicked off the entire so-called “Backpack Rap” wave included DJ Shadow’s “Endtroducing” (1996) and Lateef The Truth Speaker and Lyrics Born’s “Latryx: The Album” (1997) but it was their releases spread all throughout the era that cemented their bulletproof status in the indie Rap world. Included in this list are several more Quannum/Mo’ Wax releases including two alone from Blackalicious.

Quannum “Spectrum” feels like their version of “Wu Tang Forever” to me. It has jawns like “Concentration”, “Storm Warning”, “I Changed My Mind”, “The Extravaganza”, “Looking Over A City” and “Bombonyall” with features spanning the underground Rap Avengers lineup, Jurassic 5, Souls Of Mischief, Divine Styler, El-P and Dan The Automator.

SaukratesThe Underground Tapes [Capitol Hill/Serious](July 27th, 1999)

Story goes this album was released in Canada months before it had extra songs added to it then it was re-released and distributed in the United States in the version I covered here. I saw the video for “Money Or Love” on MuchMusic first then it aired sparingly on BET’s “Rap City”. I saw the first coverage of it in CMJ New Music Report before seeing it mentioned in XXL, Blaze, Vibe, Stress, Mass Appeal and The Source. Per usual, trying to acquire Canadian Rap CD’s without going through the typical underground Rap outlets was a stressful endeavor. Heads found a way regardless.

Anticon presents Hip-Hop Music For The Advanced Listener [Anticon](July 27th/August 3rd, 1999)

To many people Anticon represented the “backpack Rap” contigency they referred to when they used it as a slur, putdown or a derogatory term. Anticon was a collective co-founded by Alias from Maine and Pedestrian from Los Angeles and was short for “Anti conformity”. This label compilation features contributions from Sole, Alias, Deep Puddle Dynamics, Dose, Buck65, DJ Signify & DJ Mayonnaise, Pedestrian, Moodswing9, Eyedea and Slug from Atmosphere. If we’re going to talk about this year in underground Hip Hop and the indie Rap landscape we can’t do it without including this project.

Revenge Of The B-Boy [Bomb Hip Hop] (August 3rd, 1999)

Bomb Hip Hop is another indie Hip Hop label responsible for putting out independent and international Rap releases all throughout this era in addition to a grip of notable scratch/turntablism/instrumental projects. One of those notable releases being “Revenge Of The B-Boy”. Selections from DJ Format, Mr. Wiz, Jeep Beat Collective, Faust & Shortee, DJ Junk, Metabass N Breath, Looptroop, Blade, Knights Of Bass & others.

The resurgence of B-Boying stateside was aided by the explosion of international Hip Hop mailorder with catalogs selling VHS tapes of B-Boy battles, jams, competitions, pro-ams and Rock Steady Crew reunions. These videos had a similar effect that the And1 mixtapes had on street basketball, growing the discipline by leaps and bounds. However, by Summer 1999 those VHS tapes were being converted to DVDs and people began to crave the same kind of music the B-Boys and B-Girls in these videos practiced and competed to.

ArsonistsAs The World Burns[Matador](August 24th, 1999)

We were first introduced to the Arsonists via their singles on Fondle ’Em but they signed deals with Matador around the same time Non Phixion did. Their debut LP “As The World Burns” not only lived up to fan expectations but exceeded them. This entire album was a banger from beginning to end and the Arsonists’ live performances only made this album all the more enjoyable. I heard this album blasting out of headphones and cars for the remainder of the year.

I also remember recording the spilt video for “Pyromaniax”/”Backdraft” on the Burly Bear Network’s Rap video show called Hipnodx hosted by a dude named Phlegm. It got played sparingly on MuchMusic’s “Rap City” and I never saw it on BET’s “Rap City”, MTV or MTV2. Regardless, this album was a certified classic. Having it end with “In Your Town”? FAM.

High & MightyHome Field Advantage [Eastern Conference/Rawkus](August 24th, 1999)

High & Mighty were two Philly cats who I remember from when they were Boston University students. They rocked many a show in Cambridge’s Middle East. This album was dope from top to bottom, featuring guest verses from Pharoahe Monch, Mos Def, Mad Skillz, Eminem, Cage, Kool Keith, What? What? (Jean Grae), Defari, Evidence, Thirstin Howl III, Wordsworth and Bobbito Garcia. The videos for “B-Boy Document ‘99” and “Dick Starbuck” definitely helped raise the album’s profile alongside having songs appear on the And1 mixtapes and a few video game soundtracks.

Blackalicious Nia [Mo’ Wax] (August 30th/31st/September 27th, 1999)*

There’s an asterix here because Blackalicious’ “Nia” wasn’t officially sold in North America until 2000 but it was available in the UK sometime between the late Summer and early Fall 1999. It ended up in North American record stores as a UK import plus impatient underground Rap fans found ways to buy it via various international underground Rap distributors before it was given a proper release by a North American distributor. I can’t ignore that cats had both Blackalicious’ “A2G EP” & “Nia” in 1999 or the fact it technically is a 2000 release so that opens up an extra slot for this list.

AGThe Dirty Version [Silva Dom](September 21st, 1999)

I feel like this might easily be one of the most slept on & obscured classic underground Rap albums of this entire era alongside Group Home’s sophomore effort. AG and Ghetto Dwellas over production by Showbiz, Diamond D, Lord Finesse, Buckwild, DJ Premier and Ahmed seems like a must own project. When you consider there’s guest verses from Diamond D, Fat Joe, O.C., KRS One, Big Pun and Guru on “The Dirty Version” why don’t you own it? I’ve brought this album up to people just to be met with blank stares for 20 years now. Find it and get dirty.

The Funky Precedent [Loosegroove](September 21st, 1999)

Wanna talk obscure underground Rap compilations? This one the featured Jurassic 5, Dilated Peoples, Ozomatli, Breakestra, Abstract Tribe Unique, Styles Of Beyond, Divine Styler, Mikah 9, Aceyalone, Black Eyed Peas, Cut Chemist & DJ Rhettmatic amongst its contributors and the proceeds from it helped to support programs at Freemont High School in Los Angeles, Mission High School in San Francisco and Manchester Elementary School in Los Angeles.

Da GrassrootsPassage Through Time [Conception](October 5th/November 9th, 1999)

Arguably the best Canadian Rap album released in 1999. Finding a copy of this album was quite the challenge. I remember ordering it from Sandbox Automatic on two separate occasions and them not having it but they gave me a ton of extra shit to make up for it. Features from Arcee, Choclair, Saukrates, K-Os, Thrust, Elemental, Mr. Roam, Ghetto Concept & Q-Bot punctuate one of the most sought after projects of Fall/Winter 1999 to the point I don’t exactly know when it was released.

I suspect it had a Canadian release then a US release date or no one can nail down one date it dropped. All I know is cats were striking out finding a copy together and those who were lucky enough to get one rubbed it in our faces. Production was handled mostly by Mr. Attic with Swiff & Mr. Murray splitting the rest of the tracks.

Mos DefBlack On Both Sides[Rawkus](October 12th, 1999)

I really don’t feel like I need to further explain why this album is on the list. Signed, Epstein’s Mother.

Pharoahe MonchInternal Affairs[Rawkus] (October 19th, 1999)

See previous write up. Signed, Epstein’s Mother.

MF DOOMOperation: Doomdsay [Fondle ‘Em](October 19th, 1999)

Much has been written about this album… by me. One of the best things to come out of the album anniversary content wave was Bobbito Garcia himself shattering the Wikipedia myth that was this album being released on April 20th, 1999. I spent a good amount of time researching when this album was actually released to discover it was sold in Fat Beats, on the Fondle ’Em Superstore, UGHH & HipHopSite on October 19th, 1999 and later appeared in independent & box stores between November 2nd and 9th, 1999. It was re-released after KMD’s sophomore album “Black Bastards” was finally liberated 6 years after it was initially shelved in 2000 on Readyrock.

Strength Magazine presents Subtext [FFRR/London] (November 2nd, 1999)

Imagine there was an underground Rap compilation that featured Lootpack, Dilated Peoples, Del The Funkee Homosapien, Kut Masta Kurt, Rasco, J. Rocc & DJ Babu, DJ Design & Peanut Butter Wolf, Awol One & Abstract Rude, Pep Love & Jay-Biz, Rob Swift, A-Trak, Divine Styler & Aceyalone on it? Now imagine NOT copping it if given the chance back in 1999? Fuck were you even listening to?

Fat Jack Cater To The DJ [Celestial] (November 2nd/9th, 1999)

This double CD collection of tracks from Project Blowedians like Abstract Rude & Tribe Unique, Awol One, Busdriver, Aceyalone, P.E.A.C.E, Medusa, Rifleman Ellay Khule, O.M.D., Phoenix Orion, Ganjah K, Otherwize, Jizzm High Definition, Smooth 7 & Volume 10 produced entirely by Fat Jack is yet another textbook embodiment of underground Rap releases from 1999 that mainstream Rap fans have no idea even existed. Thank God some of us had actual taste…

DJ Melo D World Famous Beat Junkies Vol. 3 [Blackberry/Ill Boogie (November 9th, 1999)

The 3rd edition of the World Famous Beat Junkies compilation/mixtape done by DJ Melo D consisted of selections from Grand Agent, Chris Lowe, Saukrates, Choclair, Encore, Afu Ra, LMNO, Quasimoto, Defari, Dilated Peoples, Lootpack, M-Boogie & Mykill Miers. There wasn’t a 4th volume because Vol. 1 represented 1997, Vol. 2 encompassed 1998 and Vol. 3 embodied 1999. By 2000, we already knew what the deal was.

Blind Side Recordings presents Wide Angles [Blind Side] (November 16th/December 7th, 1999)

This compilation is remembered for containing the insane DJ Spinna remix of Big Kwam’s “Verbalize” and Pharoahe Monch’s “Tooley Crew Personified”. In addition, we have Truth Enola featuring De La Soul, Mos Def & Talib Kweli, Grap Luva, J-Live, Mr. Complex, L Swift, Big Twan , Alice Russell, Alfonso Greer, Invisible Mics & Subterrean included on here. Since this was a UK based label I feel like this one flew under the radar even more than normal as an underground release. Addition production handled by The Creators, Kenny “Dope” Gonzalez, Nick Wiz, 88-Keys & DJ Joc Max. I think we’re done here…


Several other notable 1999 releases that warranted mention but just barely missed this list include but aren’t limited to releases like “Process Of Elimination”, “Tags Of The Times 2.0”, “Defenders Of The Underworld”, “New York State Of Rhyme 2”, “Hip Hop Underground’s Finest The EP”, Sway & King Tech with DJ Revolution “This Or That”, Thirstin Howl III “Skillionaire”, Aesop Rock “Appleseed”, Rasco “The Birth EP”, Mathematik “Ecology”, Choclair “Ice Cold”, Rascalz “Global Warning”, Roots Manuva “Brand New Second Hand”, Defari “Focused Daily”, Group Home “A Tear For The Ghetto”, Visionaries “Sophomore Jinx”, Krispy “From The Country”, Superstar Quamallah “Don’t Call Me John EP”, Unspoken Heard “Jamboree EP”, Micranots “Farward EP”, Living Legends “Foxhole EP”, 7L & Esoteric “Speaking Real Words EP”, etc. in addition to turntablism albums/tapes by DJ Faust, DJ Logic, DJ Vadim, Ming & FS, El Stew, Ko-Wreck Technique (Push Button Objects x DJ Craze), Mr. Dibbs, DJ Disk, DJ T-Rock, DJ Q Bert, DJ Craze, Invisibl Skratch Piklz, DJ Shortee, DJ Z-Trip & Radar, Jeep Beat Collective, Mixmaster Mike & DJ Krush.

1999 could’ve been a transition year building up to a 3rd Golden Era but corporate interests and the rapidly changing mainstream Rap industry prevented that from ever happening. Once the many byproducts of the Telecommunications Act Of 1996, the exponential speed of communications technology and the greed of the RIAA all came to a head in Summer 1999 with the explosion of P2P sites nothing would ever be the same again.

The mainstream Rap industry and underground/indie Rap industry remained in their same holding patterns and never the twain would meet. Now you’re all caught up. In 2020, I will officially retire from doing these unless it’s going to be for a book and someone fronts me an advance for doing that kind of labor. This trilogy might end up in print in the near future as well, who knows?

If you take the time to applaud for this article don’t even waste your time on anything less than 50 claps. Hold that fucking button down down until you see a “+50” pop up. I’m dead serious. I put in too many goddamn manhours of exhaustive research on this subject over the past almost 15 years for anything less than that. Listen to my podcast Dart Against Humanity and purchase my book Best Damn Hip Hop Writing: The Book Of Dart.




Host of Dart Against Humanity/Boston Legends. CCO @ Producers I Know/journalist @ Okayplayer/DJBooth/Complex/NPR/Mass Appeal/IV Boston/HipHopWired/KillerBoomBox