Keeping It Strange: The 10 Weirdest Rappers Of All Time

Feb 19 2015

10 Weirdest Rappers Of All Time

The days of what’s “acceptable” and “unacceptable” to be considered “real hip hop” are long gone. These days anything goes, from fashion, to sound, to slang, and we wouldn’t have it either way.

In anticipation of Tech N9ne (the O.G. of Keeping It Strange) and his upcoming album Special Effects, we tallied this list of our favorite weirdos in the game. From East to West, hip hop has brought up some of the most off-kilter characters that music has ever seen, and we’re here to celebrate it in all of its unusual glory.


Brotha Lynch Hung

This carnivorous emcee has been on some other shit since the beginning of his career. As far as lyrical content goes, Lynch is arguably the most disturbed artist on this list. His lyrics consistently center around the theme of eating: everything from babies, adversaries to other emcees. While his imagery is outlandish, one cannot deny the skill he employs in making the listener cringe, as he is one of the most respected emcees in the game for his incredible delivery and intricate flow patterns.


For no sensible reason, Brotha Lynch Hung made this video of himself taking a piss and turned it into a somewhat of a cautionary tale.



Daylyt is an undoubtedly skilled battle rapper but is more widely known for his outrageous antics. Because he’s somewhat new to the spotlight, we can only put him so high on the list, but at this rate he’s easily a future contender for the top spot.


Daylyt got kicked out of a URL battle for trying to crap on stage.


Daylyt said he’d “fuck the shit out of Diddy.”


Tech N9ne

First of all, the dude’s label is called Strange Music, so there’s that. From the spiked red hair, to the religious imagery, to the downright insane way he plays with the flow, Tech N9ne has always been different. In fact, Tech’s the kind of dude that would probably be pissed that he wasn’t higher up on the list. If there’s one thing we can count on from Tech N9ne, it’s that he’s unpredictable: you never know when he’s going to release a rock EP, say some off-the-wall shit in an interview or invent a flow pattern that knocks you on your ass. Tech’s a true Klusterfukand he’s proud of it.


Tech N9ne reveals his guilty pleasure in this interview with Montreality. As it turns out “I like hot scalding water on my balls,” wasn’t just something he made up for shock value in “Am I A Psycho?” Skip to 5:53 for this all-time gem.


Danny Brown

Danny Brown is kind of like ODB if he had kept his shit together. Sexually explicit and honest to a fault, Danny’s vocal inflections aren’t the only thing coming out of left field. The thing with Danny is that his eccentricities are often also his strengths. The dude possesses a lyrical honesty reminiscent of Tech N9ne, allowing himself to express his vulnerabilities through song, often times over beats that you would never expect to give way to such open-book style content. The man also really, really likes eating pussy apparently, as it constantly comes up in his lyrics. Truer words were never spoken than, when referring to his crew The Bruiser Brigade, Danny rapped, “Bruiser make 2 Live Crew look like some Mormons.”


Danny Brown talks to A$AP Rocky about the time he got head from a toothless crackhead when he was 16. Watch this whole back and forth if you want to laugh your ass off.


MF Doom

MF DOOM is more of a mythical creature than an actual person/rapper.

Very few people have ever seen the man behind the mask, and even if they did they can’t really be sure it was him, as he’s been known to send impostors to perform shows on his behalf. This is just one of the many oddities of the man who has almost as many aliases as he does projects. Incredibly prolific both on the mic and behind the boards, MF DOOM has built a cult following with off-kilter rhymes, funky-ass beats, and a shroud of mystery constantly surrounding his every move.


Pretty much everything that happened after DOOM’s KMD days as Zev Love X. We went from seeing a young DOOM in the 3rd Bass video for “Gas Face” to trying to keep up with alias after alias, each weirder than the next. Ever listened to Viktor Vaughn, King Geedorah, Madvillain, or DangerDoom? Then you’ve heard some incarnation of MF DOOM, and hopefully you loved it.



In a very short period of time, Tyler, The Creator has gone from being written off as an overly-rebellious shock rap act to one of the most promising talents in not just hip hop, but music and art in general. While Tyler got the attention of hip hop heads everywhere with his Bastard project, he’s gone on to build a legitimate empire with Odd Future, putting on several other revered artists (See: Hodgy Beats, Earl Sweatshirt, The Internet), organizing carnivals, and directing some of our favorite videos in recent memory. With a penchant for lyrics containing extreme violence and homophobic terminology that makes Eminem look like Perez Hilton, Tyler seems to have his finger on the pulse of “How weird can this get while still being groundbreaking and awesome?” and it doesn’t seem like that finger is going to lift any time soon.


Probably the video for “Yonkers” in which Tyler is seen eating a live cockroach in an otherwise just-as-weird set of visuals. After that, it’s just gotten weirder and more awesome by the day.

4. RiFF RaFF


Is he serious? Is he joking? We’re still trying to find out. With his ability to so seriously convey the most outrageous opinions you’ve ever heard, you could call RiFF RaFF the Andy Kaufman the hip hop. But whereas an “act” can come and go, skin ink stays forever, so you really have to wonder if someone who dedicated parts of his body towards tattoos of the MTV, BET, and Worldstar Hip Hop logos is fucking around. His Versace fetish, penchant for saying the most outrageous shit, and late affinity for weight lifting puts him near the top when it comes to bizarre.


RiFF RaFF rattled off an seemingly endless stream of quotables in this interview with Fader, also revealing his alter-ego, the infamous Jody Highroller.


RiFF RaFF requests a “dungeonous Ox” at the dinner table and has put on 40-50 pounds (3:40 mark).

3. LIL B

Lil B

It’s entirely possible that Lil B is actually the latest incarnation of Buddha, which is especially weird because he was initially just known as that first dude in The Pack’s “Vans” video.

After breaking out on his own, Lil B’s music somehow turned into what we now know as “based”, often ignoring flow patterns and the act of rhyming completely, and usually containing incredibly weird and unexplained content. Lil B’s catalog has got to be one of the most divisive things in hip hop today, but love him or hate him, the man has a positive message, even if it does sometimes get lost in Instagram posts of Pokemon screen-caps and girls’ feet (Lil B is a well-known foot fetishist).

Don’t believe us? Check out his lecture at NYU & tell us you don’t thank Based God at the end.


Lil B cried in a pet store.


Kool Keith

Kool Keith, how do you explain a man whose flows are as various and perplexing as the constellations in the galaxy? He’s a legendary figure in hip hop who can change personas like we change outfits, so much so that he said “I don’t even feel like I’m a human being anymore.” After listening to anything from his extensive catalog, we’d have to agree.


Kool Keith released an entire album from the perspective of Dr. Octagon, an “extraterrestrial time traveling gynecologist and surgeon from the planet Jupiter.”


Die Antwoord1

In a post-Eminem and Tyler, The Creator era of hip hop, it’s pretty tough to shock people, but Die Antwoord seem to tackle that challenge with ease.

The South African duo comprised of Ninja and Yolandi Vi$$er have described their work as “exaggerated experience” or “documentary fiction” when asked if their output is a joke, which to be honest is a fair question after you hear songs like “Baby’s On Fire” and “Enter The Ninja”.

Music aside, Die Antwoord’s aesthetic is pretty damn weird as well. Inspired by South African photographer Roger Ballen, the group’s imagery often revolves around physical deformities, desolate landscapes, violence, and all around weirdness.


When people saw the video for “Enter The Ninja” and had no idea where these people came from. Were they serious? Was that Yolandi’s real voice? What the fuck is “Zef”? While none of those questions have been given a straight answer, the truth is we no longer care. The music is fun, the visuals are groundbreaking and trippy as hell, and we have a secret crush on Yolandi (when she’s not wearing black contacts and has blood dripping from her fangs).


Tech N9ne Special Effects Splash

  • What did you think of the list?
  • What do you think about the order? Who did we miss?

Let us know in the comments section below!