The worst rappers. Ever.


Dave in Charge has shown us that rap is a skill, albeit a skill not everybody possesses.

We might disagree with at times sexist and misogynist lyrics of rap stars like Eminem, Jay Z, Snoop Dogg, or 50 Cent but there’s no doubt that those men are artists on the microphone.

And then there are those who assume that anybody who can speak can rap.

We have put together a (not exhaustive) list of rappers that are so atrocious that we won’t take any responsibility if your ears are bleeding after listening to them.

Brian Wilson – Smart Girls

In 1989 The Beach Boys’ Brian Wilson began recording his solo album, Sweet Insanity. It was so bad that it was never released, but most of the songs sooner or later made it to the light of day. Among these treasures is the unbelievably bad rap number, Smart Girls. Nobody will disagree that Wilson is an exceptional musician, but 1989 clearly wasn’t a good year for him. In the song he addresses his sins objectifying women back in the Beach Boys days. Because he’s now a changed man who wants them look nice but be clever on top of that. Or as he puts it, “sexy legs with high IQs; Smart girls, I love the smart girls; You brainy babes with your attitude.”

Kevin Federline – Lose Control

It can’t be all that easy for a young man to be in his super-successful wife’s shadow. So it didn’t come as a surprise when background dancer and Britney Spears’ hubby Kevin Federline was aching for a wee bit of limelight too. His debut (and only) album Playing With DFire turned out to be one of the biggest failures in music history, leading the list of worst-rated albums on Metacritic ever. But staying home on his wife’s alimony isn’t so bad either …

Chicago Bears – The Super Bowl Shuffle

There’s a reason why some boys become sport stars while others become rap stars. We all have our talents and sometimes it’s just better to stick to them. In 1985 the Chicago Bears football team recorded a song called The Super Bowl Shuffle. And although the single became a mainstream phenomenon and sold half a million copies, it’s still God-awful.

Vanilla Ice – Ninja Rap

As we know Robert Matthew Van Winkle, the white rapper who calls himself Vanilla Ice, had a major hit with Ice, Ice Baby sometime in the 90s. But we don’t know if it is true that rap magnate Suge Knight dangled Mr Ice by his feet off a 20th-storey balcony as a way of making him sign away publishing rights to his smash hit Ice, Ice Baby (or to make him stop rapping).

We also have no idea what Ice was thinking when he agreed to recording the soundtrack to Teenage Mutant Ninja Turtles II. Go Ninja, Go Ninja, Go Ninja, Go!

William Shatner raps Shakespeare

Star Trek actor William Shatner is not one to shy away from poking fun at himself. In this beautiful clip we see the Canadian actor in 1998 movie Free Enterprise, where he plays himself staging a rap version of Shakespeare’s Julius Caesar in hope of finally being taken seriously as an artist. But to be fair Shatner’s musical career goes back to the 60s when he released his first album, The Transformed Man. On it he compared contemporary pop songs to the works of William Shakespeare by providing dramatic readings of Shakespeare along with dramatic readings of the lyrics of songs such as Lucy in the Sky with Diamonds.

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MC Miker and DJ Steven – Holiday

Yet another strange phenomenon is that of Dutch hip-hop duo MC Miker and DJ Steven. Their single, Holiday Rap, a song that remixed Madonna’s hit Holiday with Cliff Richard’s Summer Holiday, became an international success, reaching the top of the single charts in 34 countries. It was also named by MuchMusic as the worst video of 1987. But judge for yourself.

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