Rappers Who Were Really Weird People

There are odd people in all walks of life, but some groups can have a far higher bar for eccentricity than others. For instance, so many famous authors were really strange people that it takes some truly dedicated weirdness to stand out from the masses. Likewise, princes and princesses can count some truly impressive oddballs among their ranks. Rappers, on the other hand, are one group where it may be difficult to gauge the artist's true character. It can be hard to stand out in the music business, after all, so some musicians have personal secrets they'd rather keep under wraps. Consider Rick Ross, for example. He plays the role of a former drug kingpin when he actually used to be a prison guard. 

However, the fact that truly peculiar rappers may be comparatively hard to separate from the herd doesn't mean that none can be found. In fact, several extremely eccentric rappers markedly stand out from their peers with their sheer strangeness. Here's a look at some of them.

Die Antwoord is even freakier behind the scenes

Die Antwoord stands for "the answer," but the South African rappers have historically been more content to raise questions than they have been to provide solutions. From their early days, Ninja and Yo-Landi Vi$$er have stood out with their distinctive visual style that combines cartoonish and creepy, released offbeat bangers like "I Find U Freeky" and "Pitbull Terrier," and embraced their country's "zef" subculture. "It's like, kind of bad, but kind of like this apocalyptic debris that we've stuck together," said Ninja, explaining zef in a 2010 interview with Mother Jones. "People say trashy; it's not really trashy. It's not having money, but still f***** having style."

A part of Die Antwoord's chaotic antics may stem from their past history in other high-concept bands, but the deeper truth of Die Antwoord not only somewhat cramps their self-professed style — it also strongly suggests that the weirdness and unpredictability isn't entirely an act. Apart from the outlandish imagery the band uses in its art, Ninja in particular has created headlines for equally outlandish behavior that has led to multiple allegations, and even lawsuits, that have included accusations of grooming, sexual assault, violence, and homophobia. 

Die Antwoord has also been criticized for their use of blackface in their videos. For their part, they've lashed out against other projects they feel have stolen their look — from Neill Blomkamp's "Chappie," in which Die Antwoord actually appeared in, and the DC Extended Universe film "Suicide Squad." 

Kanye West is the poster boy of rapper oddity

In all fairness, Kanye West has had a tragic life that involves personal tragedies and mental health issues. However, over the years, he's amassed a laundry list of outlandish actions and opinions, which have managed to offend so many people that calling him strange is an understatement. 

One of the earlier major Kanye incidents — or rather, Ye incidents, seeing as he officially changed his name to this two-vowel word in 2021 – came in the 2009 MTV Video Music Awards, where he invaded the stage to protest Taylor Swift winning a video award over Beyoncé. Since then, the artist has amassed a collection of statements that range from peculiar right-wing opinions to outright hate speech. He's been spotted wearing a controversial "White Lives Matter" shirt and the "Make America Great Again" hat. He's dined with Donald Trump, bringing a known white nationalist as a guest. He claimed in 2011 that he's more hated than Adolf Hitler, and has made enough antisemitic remarks that in 2022, several companies ended their partnerships with him.   

Kim Kardashian often witnessed West's behavior and outbursts both during and after their marriage. She's rarely spoken about the situation, but on "The Kardashians" Season 3, Episode 1 (via Harper's Bazaar), she briefly addressed how difficult things have been. "The one who does interviews saying they're my 'forever protector' is the one hurting me the most," Kardashian spoke of West.

André 3000 just wants to play his flute

From the genre-bending Southern hip-hop duo OutKast to the smash hit "Hey Ya!" on the duo's twin-solo-albums-but-not-really endeavor "Speakerboxxx/The Love Below," there was a point in time where it seemed that André "André 3000" Benjamin was destined to become a giant crossover sensation. He could rap, sing, play instruments, produce, act, and then some. 

Though André's look and sound made him stand out as one of the more eccentric rappers, he was stylish, creative, charming, and gave a great soundbite. "I rarely drink, I don't smoke, so my vice is probably creating. I'm addicted to creating. And women," he told The Guardian in 2005. The very next year, OutKast put out one more record, "Idlewild." After that — crickets. Apart from the occasional quick feature, André 3000 essentially disappeared from the public eye.

Starting in 2019, the rapper's music started making waves again ... but this time, it's because people started spotting him in different places, just hanging out and playing the flute at airports and open mics. This new hobby led to a 2023 comeback album, which turned out to be an instrumental flute album called "New Blue Sun." If that's not eccentric enough, André informed his fans why he chose this particular medium, instead of returning to the genre that made him famous, by naming the first track, "I Swear I Really Wanted To Make A Rap Album, But This Is Literally The Way The Wind Blew Me This Time." 

Insane Clown Posse: Gang leaders, wrestlers, woke trailblazers (depending on the viewpoint)

An uncharitable person might label Shaggy 2 Dope and Violent J — together known as Insane Clown Posse (ICP) — "white trash" and be done with it. Both men have had trouble with the law. Apart from their rap career, they have a long history in pro wrestling. Even Insane Clown Posse's fans, or "Juggalos," are a community of outcasts that the FBI classified as a gang in 2011. However, switch the point of view, and you'll find a recognizable and highly successful DIY brand: They have their own music, merchandise, and even a long-running Gathering of the Juggalos festival that keeps attracting audiences old and new. Building all that with barely any Billboard success is no mean feat.

There's also a third angle. When the FBI gave Juggalos their gang classification, ICP ran to the fandom's defense and teamed up with the American Civil Liberties Union to sue the agency and the Department of Justice. They also arranged a march on Washington, and analyzed the gang designation's flaws and consequences on outlets like Time — in full facepaint, of course. 

This isn't the only time ICP has come across as outright progressive. The duo hasn't been afraid to acknowledge old insensitive lyrics, and were among the first to cancel their 2020 festival amidst the COVID-19 pandemic. Consider all this, and whether you love or loathe their clown style, Shaggy 2 Dope and Violent J are clearly among the stranger and more complicated rappers out there.  

Flavor Flav: The clocks are just the beginning

Flavor Flav has often been a man of contradictions. While his wild and cartoonish presence counterbalanced the stern, serious Chuck D in Public Enemy, he may well have been the most talented musician in the group, as he came from a church choir background and could play multiple instruments. While Chuck publicly stated that the group steered clear of alcohol and drugs, Flav struggled with addiction for years. Many people who were watching TV in the 2000s may remember Flav as a harmless, fun eccentric from his string of reality shows. However, the rapper also has a history of unsavory behavior that has landed him into all sorts of trouble, legal and otherwise. 

When he was just a boy, Flav burned his home by accident, and he went to jail several times before he was of legal age. During his darkest years in the 1990s, Flav was a constant courtroom presence thanks to various domestic abuse and drug cases ... and he even attempted to shoot his neighbor in 1991. Put this together with some family drama and tax and child support issues, and it's no wonder you don't hear from Flavor Flav too much.

As of 2024, Flav seems to be in a better place, but he's keeping things characteristically strange. He's making music with Chuck D, but he's also been reinventing himself as ... Taylor Swift's number one fan, "King Swiftie." 

ODB just wanted to educate

Wu-Tang Clan is full of big personalities, but even then, the man who chose Ol' Dirty Bastard as his stage name found no trouble standing out. ODB was among the founders of the group and even achieved some solo success outside it, but his personal life was rarely peaceful. In fact, as his 93-page FBI file shows, the rapper was arrested no less than 15 times, and the authorities suspected him of all sorts of things, from connections to two murders — and attempting to murder a police officer for good measure — to drug trade and gang affiliations. 

However, the file surfaced years after the tragic accidental overdose death of ODB in 2004. During his lifetime, the eccentric rapper was known to be less than law-abiding, sure — but arguably, his outlandish antics were even better known. 

In 1998, ODB rushed the Grammy stage, grabbed a microphone from Shawn Colvin, and delivered a lament about Wu-Tang Clan losing an award to Sean "Puffy" Combs. "Wu-Tang is for the children. We teach the children, you know what I mean? Puffy is good, but Wu-Tang is the best, OK?" ODB educated the audience. He once turned up to drop a verse during a Wu-Tang Clan album release party, despite being a fugitive from the law, and on another memorable occasion, he dropped by to pick up food stamps ... in a massive limousine. 

Pras Michel went from music to political conspiracies

At the beginning of 2022, iconic 1990s hip-hop trio the Fugees canceled their reunion tour, citing the COVID-19 pandemic as the reason. However, it's worth noting that one member of the group, Prakazrel "Pras" Michel, already had his hands full in the U.S. — not because of a solo album, but because he was facing charges for political conspiracies during both Barack Obama's and Donald Trump's presidencies. 

This is not among your typical rapper's extracurricular activities, but according to the feds, Pras isn't what you'd call a typical rapper. Since 2006, he's known Jho Low, a Malaysian businessman known as a high roller who funded movies like "The Wolf of Wall Street" ... and lived in a lavish fashion not unlike the bacchanals on display in that Leonardo DiCaprio film. Unfortunately, the money Low was playing with wasn't entirely his own, and he was actually siphoning billions from a Malaysian sovereign wealth fund. 

When the cat eventually got out of the bag, Low was nowhere to be seen, but Pras was accused and eventually convicted of puppet-mastering a massive pro-Low conspiracy on the financier's behalf, feeding Low money into the 2012 Obama campaign through assorted channels to gain influence — and later making moves within the Trump administration to make the embezzlement charges against Low to disappear. It's a wild political thriller for a rapper to become entangled with, and a far cry from performing "Ghetto Supastar" live at the MTV Video Music Awards. 

B.o.B. is a flat Earth theory enthusiast

B.o.B. might not be the most iconic name on this list, but he's certainly had his share of Billboard hits with songs like "Airplanes," "Magic," and "Nothin' on You." He's also made quite a few waves in media — though these have often been more related to his beliefs than his music. 

The Atlanta-based artist is a full-blown conspiracy theorist who's not shy about letting the world know about his views. Over the years, B.o.B. has made clear that he believes in the 9/11 myth that jet fuel couldn't possibly burn hot enough to melt steel and bring the World Trade Center towers down. He's also suspected that "the enemy" clones people, and that enslavement didn't exist. However, he's probably most famous for his long-running and vocal subscription to the flat Earth theory.  

2016 was a banner year for B.o.B.'s flat Earth beliefs, which soon escalated to a situation where he was exchanging diss tracks with astrophysicist Neil deGrasse Tyson. The latter spent quite some time trying to educate the rapper on X, formerly known as Twitter, and later quite literally dropped the mic on the subject during an appearance on "The Nightly Show with Larry Wilmore." Unperturbed, B.o.B. went on to try and raise funds to research his theories with the aid of satellites, though a lack of further news on this front suggests that he hasn't managed to put his space fleet together. 

Donald Glover wants to emulate Willy Wonka

"Weird" doesn't automatically mean "bad." On the contrary, Donald Glover has a decent claim of being a visionary between his Grammy-winning rap career as Childish Gambino, and his Golden Globe and Emmy-winning movie and TV careers. Where it gets strange is how he goes about staking said claim. 

Glover is known for combining the outlandish with the all-too-recognizable. In an interview with Interview Magazine — in which the "Atlanta" star and creator characteristically added a dash of absurdity by interviewing himself — Glover opened up on his approach to artistry by comparing himself to a certain famous fictional candymaker. "Willy Wonka. That's the world I like," he said. "You have your factory, you make something, put it out, and then close shop to the public for a while." 

This talk about wanting a Wonka-style hideout wasn't entirely metaphorical. While he hasn't built a candy factory (yet), Glover has created a farm compound he calls Gilga, where he and other creators work on whatever projects occupy their mind — which, for Glover, is pretty much everything, up to and very much including farming. In an interview with GQ, he explained Gilga's mission of cultural freshness with an appropriately agrarian metaphor. "You know how you go to a farmers' market and you ask for peaches, and they don't have any because they're out of season?" Glover said. "Peaches have a season! I'm not gonna sell you s***** peaches just because you want a peach now."

Popek Monster lives life to the extreme

Polish rapper Popek – aka Popek Monster — is so outlandish that he's actually turned up as part of a fake news story to make it slightly more believable. In 2015, a fake tale about a lottery winner who died after gold-plating his private parts featured an image of Popek holding some bling and a stack of cash money.

Popek's aesthetics are indeed eye-catching. He's a hulking man with scarification marks on his face, golden teeth — which he once teased he might pull off and give to unhoused people — and eyeballs that have been tattooed black, which he thinks cost him an estimated 35% of his vision. He also boasts a considerable number of more traditional tattoos, which are often visible due to his side gig as a mixed martial arts fighter. 

In a 2019 Noisey documentary about Popek, the rapper's unique approach to life is on full display. He greets the host by pretending to be blind and charging at the guy with a handgun. He recounts his experiences with substance misuse, which he claims once left him in a coma for six months. Perhaps most amazingly, we also find out that he's competed in the Polish version of "Dancing With the Stars," ballroom dancing like there's no tomorrow. All in all, Popek Monster is just about the furthest from an ordinary guy that you can get. 

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