Top 5 Craziest, off the wall MC’s


Oh insanity!!! We all think we’re sane, but then when poked and prodded by mad doctors, you get the feeling that it might be you who is in fact insane. One of the best lines on insanity was uttered by one of the greatest and most eccentric artists, Syd Barrett of Pink Floyd fame, before Roger Waters went shmorgesboard all over Israel and it’s dastardly deeds.

Syd is one of the founding members of Pink Floyd and he wrote almost all their early hits, and misses until he took the acid thing too far. However, in an interview with Roger Waters he recalled that a psychiatrist noted to Syd that he has a mental issue. Syd retorted by saying, well maybe it’s the world that’s truly insane! or that maybe this is your issue, but not mine! Unfortunately Syd had little output after releasing two solo albums, and plenty of bootlegs and unreleased material. He slowly dove deep into the dark corners of his mind, and wasn’t seen from again, until 1975 when he traumatized his ex-band members during their recording of, ironically, Wish You Were Here. Syd remains quite an inspiration, not only to rockers but to certain hip-hop heads as well. Just check Edan’s first album, Primitive Plus. Inside the album there’s a sheet with faces of inspiration ranging from Jimi Hendrix to Just-Ice, and right smack in the middle is Syd Barrett. So, in honor of Syd and insanity here’s my list of the top 5, with an honorable 6th man, craziest off the wall MC’s in the history of Hip-Hop.


#5 – Kool Keith – Kool Keith is known by many different names, and is so diverse in his world that you can catch him watching a baseball game in the Bronx while eating pink cotton candy and sporting a green speedo, or catch him at the strip club in L.A. giving out free baggies of fried chicken, HiC juice, and a wet nap (I managed to catch one at a show in New Haven’s Toad’s Place). We all first heard him on wax along with his critically acclaimed group the Ultramagnetic MC’s whose style was both spacey and fully confrontational. Keith, who has made a residence in many places, including Bellevue Hospital’s psychiatric ward, takes on, or has discussions with all his inner voices that come out as full-fledged characters, with such diversity and pomp. He’s brought us to the bleak experiments he conducts in a subterranean hospital in the guise of the evil Dr. Octagon,

He’s taken us through the bizarre ride of his sexual fetishes and porn obsessed mind as Kool Keith,

He’s taken us to the nether regions of sexual space in the guise of Black Elvis,

He’s teamed up with Motion Man, and the great beat maker Kutmasta Kurt to become a cartoon Master of Illusion,

He’s made a funny live action video as the Bushman,

and that’s just the tip of his Ice-burg (no pun intended). He has many more characters locked in his head, and we hear their words from time to time. He also hasn’t slowed down on creating, as well as talking smack about the rap game as he does on the song and video “Goodbye Rap,” as his ode to the culture and how it changed. Interestingly enough he also talks smack about the old methods and notions of the rap game.

Keep up the crazy critique Keith.


#4 – Rammellzee – This is the original (OG) crazy man of Hip-Hop. He also hung out with another eccentric artist who was big in the 1980’s by the name of Jean-Michel Basquiat,

and he should be considered one of the first Hip-Hop renaissance men. He mostly stuck to graffiti and other visual art forms, but he also recorded one of the most iconic songs in rap music, “Beat Bop.”

There is so much going on in this collage of sounds as we hear the dialogue between a teen, thanks to the young K-Rob, and a drug dealer voiced by Rammellzee. Rammellzee also has such a distinct style of rapping about the life of drugs, while he also uses non-sensical words while streaming them along with the beat. This is considered one of the first alternative and far from conventional rap songs ever released. The single’s artwork was done by Basquiat and to date is the most coveted item among rap’s historical artifacts. Rammellzee continued to record some music, produce art works, and kept his manic appearances bizarre as always, while pushing the limits through his art using language as design, while providing the basis for what he termed AfroFuturism.

Unfortunately he passed away in his home in Queens in 2010. However, his influence as well as the influence of “Beat Bop” could never be downplayed, and is still reverberating through space. His spacey apocalyptic visions on wax have influenced rap outfits like the Anti-Pop Consortium, and El-P, and the song has been sampled by the Beastie Boys on two separate occasions. RIP, Z’L and now you’re in and with the stars!


#3 MF Doom – Like Kool Keith, Doom takes on the many personalities lurking in his head, behind the eyes, and below his cerebral cortex. However, unlike Keith who was born with his instability, Doom took on his persona much like the comic hero he emulates. Doom came from the ashes of tragedy and trauma, hence his style is so unhinged, and unbound by the human ear. Originally part of the group KMD along with his younger brother, the group released a solid debut album, only to have their second album shelved due to controversy. During that time period his brother, Subroc, was hit and killed by a car. This caused Doom, who was known as Zev Luv X at the time, to go underground for a few years while immersing himself in Jazz, and other music, as well as beer and the sounds of his brain talking back. What came out of this underground was MF Doom, dropping the comic book style debut Operation: Doomsday! 

The beats were solid and full of old comic book Saturday morning cartoon dialogue along with funk breaks and samples. However, it wasn’t only the music, but the words that he spits a mile a minute.

Just dropping lines like “On the slow-mo the calm artist with the so-so chick, Chased them all like how he did to Slobodan Milosevic.” Bizarre, but poignant at the same time. Also like Keith he’s taken on various characters in order to embellish on other aspects of his erratic personality. Whether it be one f the two albums under the name Viktor Vaughn, reaching to the darkest recesses of an evil doer,

Or under the guise of his city crushing monster Island czar, King Geedorah,

Or his amazing collaboration with the beat-smith extraordinaire Madlib as the Madvillian,

Or dropping the MF and leaving the Doom on his insanely underrated album Born Like This,

Or most recently adding the letters JJ, hence JJ Doom, and in this case the JJ belongs to the producer Jneiro Jarel on his last solo album Key to the Kuffs,

Most recently Doom has been mentoring an up-and-coming MC by the name of Bishop Nehru, and who knows what’s next for the man behind the mask. We’re still waiting patiently for the second Madvillian album, as well as the mythical collaboration with Ghostface Killah. But he might drop a solo out of nowhere, including supplying beats for a countless stable of MC’s. The question is, what’s next in the mind of this amazingly original MC?


#2 – Ol’ Dirty Bastard – The man, the myth, the father of all styles that has no father to his styles. Much can be said, written, and insinuated about the man we call Ol’ Dirty, or any other name from Dirt McGirt to Asun Unique. Like most of us the first time I heard him was on the debut album by the Wu-Tang Clan, Enter the 36 Chambers. Dirty, along with his cousins the RZA and the GZA were the original founding members of the Wu. Once they branched out by bringing in other members his style still remained oft kilter and unique. Each member of the Wu-Tang has such a distinct voice, personality, and character, but his was truly unique and insane in its own way. He would rap off-key while bellowing out tunes as he rapped over that. On the song “Da Mystery of Chessboxin'” he belts out that he gets “low like Jacques Cousteau,”

He gets far more ruthless and raw on “Shame on a Nigga,” belting out, “Shame on a nigga who tried to run game on a nigga,”

His debut solo album is chock full of that spontaneous spitting while singing, and all packed with pure raw emotional energy and grit. He glides and slides from a party anthem like the song “Shimmy Shimmy Ya,”

Combining that 1970’s Soul Train cool  tinted with James Brown performance, with the bizarre ghetto I don’t give a shit style by wearing nothing but boxer shorts. This grit is displayed further in his amazingly dilapidated Brooklyn anthem, “Brooklyn Zoo.”

This is one of the greatest ghetto anthems full of gold vampire fronts, nasty urine soaked hallways full of people pushing each other around, while Dirty yells out that you best to run, or get the fuck outta Here! and stop acting like a pig trying to hog shit. Dirty’s debut is packed with these renditions where you’re enjoying his company while he’s constantly reminding you that this is a ride through the dark side of town. His second album is a bit different, but he still belts out the songs while rhyming in his unique way. This time he veers from the raps to the smooth Rick James style singing on top, as we see on the cover as he dons the Rick James look.

He says it best in the beginning of the title song “Nigga Please,” by saying that “My words can’t be held against me, I’m not caught up in your law.” Ol’ Dirty was embroiled by the law, but you hear how he lives on another plain, or plane, of existence like his cohorts on this list. Unfortunately he passed away in 2004 due to a drug overdose, but like that line I still believe that his soul is spiraling out in space, reaching other regions in the multi-verse, so keep your eyes open.


#1 – Redman – Red, A/K/A Reggie Noble can do many things when listening to his albums, especially the early ones. The man straight out of Jersey can make you laugh, cry, sing, think, and laugh some more due to his range as well as his no bullshit take no prisoners credo. He truly doesn’t give a fuck, which is solidified in many ways including a segment I saw on the Hate your Mom’s Loved the Videos Series. The DVD begins with a Redman show, that is then stopped, and then a fight breaks out while he’s just standing in the middle of it all with a giant smirk on his face. From his debut he broke the mold, not only being extra grimy and gritty, as we see in his love song “Tonight’s Da Night,” from his debut What: Thee Album.

Not only did he drop some gritty lyrics, he also handled production on most of his albums giving us a taste of the funk. He was the first on the east coast to use funk beats and George Clinton samples that were mostly used by west coast producers and artists. He revolutionized the game while veering from the playful to the more dark, as we hear on his second album Dare Iz a Darkside. Here’s an example from the single “Funkorama.”

It seems like he became ever more unhinged and experimental by his third album, and my favorite, Muddy Waters. Whether it’s a Blues Brothers themed video with Method Man,

Or taking us through Newark, New Jersey in his video for “Pick It Up,”

Or his moments of slapstick comedy used in the videos for his fourth album “Doc’s Da Name” (I hate how rap albums at the end of the century added the 2000 for some reason), in videos for “I’ll Be Dat,” and it has to be uncut,

Or chilling on the couch while he spits hot fire on “Da Goodness,”

Or his constant collaboration with his brother from another mother and Wu-Tang star, Method Man,from the album Blackout!,

As well as the most recent collabo,

Redman is also unique in the fact that, unlike most rappers, once he blew up he remained in his neighborhood of Newark, NJ. He also hasn’t changed much as we can always count on getting jacked in Newark by none other than Redman, what a privilege.


Honorary #6 – R.A. the Rugged Man – You definitely have issues if you’re an up-and-coming rapper who’s about to be signed to a label, and then tank it for no apparent reason. Unless, there is a reason or if the methods of losing the deal are hilarious. Hence, we have R.A. the Rugged Man. He wrote the book, or shall I say the list, in Ego Trip’s Book of Rap Lists, on 10 ways to get dropped from a record label. The list is funny where he advises to bootleg every song you make, dissing your cohorts openly on the radio, and keeping the label heads on the edge of fear each time you pass by. He remains an enigma while constantly making music that defies category such as his song “Holla-Loo-Yuh” along with Tech N9ne & Krizz Kaliko,

To his more recent commentary on the media, accompanied by a strangely entertaining video for the song “Media Midgets,”

Where he not only chastises the media, but all the news and pop culture mediums that perpetuate these stupid formulas. These formulas are so safe that an artist like R.A. would throw them far off the center of their gravity. He’s the People’s champ, and although he’s been blackballed by the powers that be in the music industry he never lost his crustified edge.




#SydBarrett #KoolKeith #MFDoom #Doom #JJDoom #Rammellzee #Ol’DirtyBastard #Redman #R.A.TheRuggedMan