Top 10 Most Difficult Songs to Rap

#10: “Can You Keep Up?” (2011)

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Busta Rhymes feat. Twista (NOTE: Please read “feat” as “featuring”) If rapping was an Olympic sport, Busta Rhymes and Twista would be competing for gold medals. This song has the two emcees flexing both their technical prowess and their lyrical skills. The title is basically a playful taunt. Right out of the gate, both rappers are delivering verses with such ferocity that it’d be a struggle to keep up if they slowed down even 50 percent. At different points, Twista compares himself to “Talladega Nights” protagonist Ricky Bobby and world-champion sprinter Usain Bolt. Rapping like this isn’t exactly the same as car racing or sprinting, but all three require absolute focus and perseverance to succeed.

#9: "The Originators" (1990)

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Jaz-O feat. Jay-Z Jay-Z’s debut album, “Reasonable Doubt,” was released in 1996, but he had been rapping for years before then. He appeared on multiple songs by his mentor, Jaz-O, a.ka. The Jaz, who also helped inspire his stage name. If you don't know Jaz-O, "The Originators" is quite the introduction. Once the flow starts, it does not let up. With Jaz’s lightning-sharp delivery, you can see why Jay-Z would idolize him. And Hov isn't just along for the ride. The baby-faced Jay delivers his lines so rapidly but so naturally, you can see he was destined for stardom. The smooth beat, produced by Jaz, is another great quality. Jay-Z didn’t become a star overnight. But with skills like these, it was only a matter of time.

#8: “Tha Crossroads” (1996)

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Bone Thugs-n-Harmony One of the most emotionally affecting hip-hop songs ever recorded is also one of the most technically impressive. On their number-one hit “Tha Crossroads,” Cleveland rap legends Bone Thugs-N-Harmony tribute those who have gone before them, including fellow rapper Eazy-E. The tone is mournful but also hopeful, reminding us that “gone” doesn’t have to mean “forgotten.” They also manage to display their individual and combined skills, with varied and fast flows and beautiful vocal harmonies. Not many songs can make us cry and drop our jaws at the same time, but “Tha Crossroads” is a very special case.

Redman First impressions are crucial for rappers, and Redman’s first single is one for the ages. On “Blow Your Mind,” the New Jersey emcee describes himself as having “styles as hard as tree trunks.” Then, he proceeds to start rapping in Korean. Decades before the K-Pop revolution, Redman was bringing cross-cultural lyricism to hip-hop. If you happen to be fluent in both English and Korean, you might be able to pull this song off. But even then, it’ll take some practice to get anywhere near Redman’s level. This song blew our minds when it first dropped and continues to do so.

#6: “Jus’ a Rascal” (2003)

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Dizzee Rascal British rapper Dizzee Rascal was just 18 years old when he dropped his classic debut album, “Boy in Da Corner.” But his skills on the mic put him ahead of plenty of his older peers. On “Jus’ A Rascal,” Dizzee’s flows are exactly that, moving so fast, you might need to reach for the Dramamine. It’s not a hollow display of technique without anything to say, however. Rapping about the stress he's experiencing and his need to succeed, Dizzee Rascal sounds unbelievably hungry. If anyone was doubting him after hearing this song, they’d be downright delusional.

#5: “Mr. Tung Twista” (1991)

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Twista If Twista never went down the rap path, he would've made a great auctioneer. The rapper more than earns the title "Mista Tung Twista" with this song, which has him running through verses like he's trying to break the vocal speed limit. But he sounds completely in control. At the end of "Mr. Tung Twista" is a teaser about his then-forthcoming album, “Runnin' Off at da Mouth” suggesting it would meet the standard set by this song and then exceed it. Twista has been listed in the Guinness Book of World Records for being the fastest rapper on the planet, able to fit 598 syllables into 55 seconds. Think you could easily do that? Think again.

Eminem feat. Juice Wrld Other artists, after accomplishing as much as Eminem has at this point in his career, might decide to just play it safe from then on. That’s seemingly not an option for Marshall Mathers, who’s as formidable as ever in his late 40s. On this highlight of the album “Music to Be Murdered By,” Eminem proves himself to be an absolute monster of a rapper. He’ll deliver a flow so astonishing, it defies all logic, and then follow it with one that makes the previous verse look easy by comparison. Forget King Kong. How about seeing Eminem and Godzilla square off?

Rich Gang feat. Young Thug & Rich Homie Quan Young Thug is one of the most influential rappers working today. So, it’s easy to forget how jarring his eccentric style was when he first rose to prominence. “Lifestyle,” an ode to success with fellow Rich Gang member Rich Homie Quan, features some ultimate Thugger phrasings and deliveries. His flow isn’t the fastest, but the way Young Thug phrases things is as difficult to replicate as it is to transcribe. And when you can make out what he says, he can stun you with his creativity even further. He might be Young Thug, but at this point, he’s an old pro.

Tech N9ne feat. Busta Rhymes, Ceza, D-Loc, JL B.Hood, Twista, Twisted Insane, U$O & Yelawolf If there’s a fast rapper equivalent of “Avengers: Endgame,” it’s “Worldwide Choppers.” On this stunning posse cut, Tech N9ne and eight other syllabic sultans from around the world, including Busta Rhymes and Twista, redefined the meaning of the word “fast.” On the hook, Tech N9ne says he’s “light years ahead of [his] peers.” But what makes “Worldwide Choppers” so much fun to listen to is the sense of camaraderie. You can feel these rappers all trying to bring out the best in each other but still want to win out in the end. As far as we’re concerned, they’re all tied for first.

#1: “Rap God” (2013)

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Eminem Referring to yourself as a “rap god” is a pretty bold statement. But if anyone deserves to do so, it’s Eminem. This song, off of "The Marshall Mathers LP 2," finds Eminem confirming himself as a hip-hop deity, spitting absolute fire for six minutes. Listening to "Rap God," you get the sense that Eminem could rap for 30 minutes straight without taking a breath if he really wanted to. When Eminem describes his lyrics being delivered at “supersonic speed,” it barely feels like an exaggeration. This song set a world record for being the hit single with the most words, 1,560 to be exact. What's even more amazing is that we're sure Eminem could break that record again.