Well, when I first heard the term, I thought it was an actual place. lol. 

You can laugh at me or with me, but that is the truth. I may have been about thirteen at the time. I was in junior high school, and one of my neighbors was a friend of my older sister, so he was about four or five years older than me. I thought he was cool, because he had a real chill persona, always had the best clothes, and was always into different music--- particularly Hip Hop. He knew a lot of different artists, and also kept up with the latest dance moves--- something I was always into. This was the early nineties, and he was the first real "Hip Hop Head" I had ever met, long before I even knew or used that phrase. One day, I think he was playing "Ya Mama," by the Pharcyde, rapping along with the lyrics. And me being intrigued by both the song and his knowledge of it, asked "who is that?" When he answered me, I asked him where he got the music from (we lived on a VERY SMALL military base in a VERY SMALL desert town). He said "that's Underground". And I asked "Where is that?" Lol. Anyway, I have spent many years trying to find that guy, because he would not believe the artist I turned into. Back then, I was a chubby sort-of nerdy, brainy kid. I later determined that I probably was destined to be a backpacker of sorts--- the kid that doesn't quite fit in, but somehow finds a group of kids that "fit in" with the "don't-quite-fit-ins". Yeah, that guy. But that was my introduction to the term "underground."

What is "underground"?

High school for me was so different because, now, having moved to a different city (in North Louisiana), and Hip Hop/Rap getting more coastal (East vs West), I had an ear for "boom-bap rap," so Rap City, Yo! MTV Raps, and hearing music on Def Comedy Jam segments was what piqued my interest. I still wasn't keen on the term "underground." After all, if it had anything to do with something or someone being "hidden," the fact that I was hearing it and seeing it on TV was an indication that it wasn't. I was into artists like OC, Biggie, Black Moon, Nas, Das Efx, Wu-Tang, Redman. And these were artists that I would see on TV. 

So, what is "underground"?

As I got into college, and suddenly started finding a personal interest in freestyling with friends and strangers between classes, someone beatboxing or beating the table during mealtimes, I became more intrigued by the artform of rap itself, and the variety of different styles that I would hear in music, with artists like M.O.P., Heltah Skeltah, OGC, Smif N Wessun, DMX, Jay-Z, Big Pun, Busta Rhymes starting to have more commercial success--- "commercial" being another term that was often contrasted with "underground." For context, search engines were just becoming popular--- Yahoo, Excite, Lycos as the leaders--- along with new websites going up everyday where information and articles could be found on different artists along with access to hear and purchase their music.

Somewhere in the late nineties/early 2000s, the term "underground" was being used to not just describe what was thought to be really good and authentic Hip Hop by artists that had limited exposure, it started to be regarded (BY MANY) as a specific TYPE of music and artistry, almost refusing to make anything that had a hint of crossover appeal. Some rappers even tried to steer clear of making anything that might cause someone to dance--- or even smile. "If it ain't grimy and grungy, you might get your "rap card" taken from you," was the sentiment. Anyone with a large recording budget, radio play, and anything shiny, was typically considered commercial. It's like it was a class or caste system to indicate who was the purest and most authentic to the culture, and who had "sold out". "Independent As Fuck," a phrase created by Company Flow, a new-york based group that was making serious moves in the underground, became an associated mantra for the underground "purists," while the group itself maintains that their intentions was not to "stay underground," but were verbally and jokingly reacting to the very kitchen-tablish work that was being done to put out their own music. Nonetheless, that phrase and others were starting to make Hip Hop an actual internal culture war, where rappers and producers were trying to navigate how to maintain their own personal integrity and artistic convictions, while building a fanbase that was not always so forgiving for artistic-evolution and experimentation. 

The fans themselves were feeling the pressure as well, having to be careful to not be found dancing to a Nelly song at a club, while all but being forced to bob their heads to "Come Clean" by Jeru The Damaja. I'm being facetious obviously. But that was how many felt during that time. Even DJs were having to make tough decisions about what to play and where. It's like everyone was trying to figure out how to define Hip Hop and their respective positions within it. (By the way, that still goes on today). Cultural preservation was serious even while the culture itself was barely twenty-five years old at that point. It's interesting what was happening, because independent labels like Rawkus, Def Jux, and Rhymesayers were actually growing to a level that eventually blossomed many promising careers in music, including artists like Mos Def, Talib Kweli, Pharoahe Monch, El-P, Aesop Rock, and Murs (to name a few). A host of other artists like Rasco, Planet Asia, Living Legends, Ras Kass, Dilated Peoples, and others were experiencing exponential growth internationally while not necessarily experiencing high-level commercial success domestically. Eminem's Slim Shady Lp came out three months before Rawkus's Soundbombing II, which contained a solo song by the white Detroit rapper. And clearly Roc-A-Fella, an independent label, launched the careers of Jay-Z, Camron, and Kanye West--- all of which became multi-millionaires--- from music or otherwise--- but definitely after having success in it. Everyone was trying to figure it out. 

So, creativity and cultural authenticity were at war with each other in the minds of both artists and consumers. And "underground" became a term used to describe who some thought were making the "best" music AND where it was thought that they should remain. Suddenly selling MORE became equated with selling OUT. And artists had to make tough decisions for the sake of their overall careers. Some of the risks actually gained individuals the commercial success AND the badges of honor for the level of skill maintained in their artistry. Who would have thought that The Roots, the Philadelphia-based live-band group, who faced all sorts of challenges for who and what they were, would go on to be the Tonight Show band? Black Thought is my favorite emcee, and has been since 1999, and I didn't see that coming--- by a long shot. 

So, what is underground? Who is underground?

I submit to you that the underground/commercial divide was contrived by people who had a fear of losing something, a personally-held standard of measurement for integrity (typically amongst others) they thought would be compromised if they or the artists "tasted" anything that had any type of a pop or crossover sound--- like a vegan afraid to admit that the taste of ANY meat would cost them the right to hold on to the label "vegan." A lot of it was peer-motivated, being afraid your homeboy would find out you borrowed your sister's Ja-Rule CD, all while that same homeboy is hiding that he bought tickets to take his girl to a 112 concert. And if some "underground" artists were honest, they would admit that much of it is motivated by jealousy of artists' success; and the only "trophy" they can control is the elite epithet of "underground."

Nah, for me, underground just means that the artist, producer, emcee, whatever, is not as well-known by the masses. They're somewhat buried underneath a pile of other artists--- for whatever reason--- thus, they only get celebrated by those who dig and/or live under the surface. While I do think that there are A LOT of great artists who should have more financial success and notoriety, every artist has to run his or her own course, put in the work, hope for the best, and maximize opportunities as they present themselves. What is considered good music and what isn't is very personal.