The Best Freestyle Artists In Hip Hop

Freestyling is often recognized as being a big part of the hip hop genre. Most of the great rappers are also great freestylers, but it is rare that you hear artists being recognized as being exceptional freestylers in particular.

As a hip hop artist myself, I grew up not only freestyling all the time but also watching all the great freestyle videos on YouTube. Everything from epic Sway In The Morning appearances to viral uploads of random guys killing it.

Here are my top 5 best freestyle artists of all time.

#5 Juice WRLD (Rest In Peace)

In an interview Juice WRLD was quoted as saying that he would freestyle his entire album. Other artists would watch the way he worked in the studio and be blow away. It was said that Juice would not only freestyle a hit song in one take, but then proceed to do the same thing again and again in the same studio session.

What makes him rank #5 on this list in particular was his freestyles on Tim Westwood. Juice WRLD sat there and rapped for an hour straight not even missing a beat. And he did it over old school Eminem instrumentals that are way out of what most modern rappers would be heard rapping over.

#4 King Los

King Los is not a name you hear mentioned at the forefront of hip hop as much these days, but back about 10 years ago he was listed by some rappers as being more talented than Kendrick Lamar.

King Los’ freestyles on Sway In The Morning are some of the best of all time. What makes them most impressive is the way you can tell the whole thing was improvised on the spot. There’s not a single point that comes across as being written or “pre-meditated”. Sway was even throwing him words to incorporate as he was going along. It was a legendary moment in hip hop, solidifying Los in the top 5 category for freestyling.

#3 Eminem

Eminem is widely known as being one of the greatest rappers of all time. Eminem actually got his start by rap battling, which can be seen in the 2002 film 8 Mile, in which he also starred. These rap battles were almost always off the top and were often spontaneously improvised in the moment, which takes a great deal of technical skill.

On top of that, Eminem has been known for doing freestyle radio appearances over the years. He has been a regular guest on Tim Westwood since the start of his career, and is always known for giving great performances. He also did a legendary back and forth freestyle with Big Proof for MTV back when he was first getting on the scene which is an all time great moment.

#2 MC Juice

MC Juice is most known for winning against Eminem in a rap battle called the “Scribble Jam” back in the mid 90s before Eminem was actually famous. As a fellow Chicago native, Juice WRLD actually gives homage to MC Juice as inspiration for where he got his name from.

Over the years MC Juice was known as being a top tier battler, with some of the best freestyle skills in hip hop. Even to this day, he continues to be a great freestyle artist, with song names such as “Freestyle Or Written” and album titles such as Every Line On Point.

#1 Proof (Rest In Peace)

Proof was Eminem’s right hand man and was considered by Em himself as being the best freestyler he’d ever heard. When you watch old footage of Proof, you can see why he said that.

Eminem was also quoted as saying that almost every time Proof freestyled he would improvise something completely fresh with “maybe one or two lines that were pre-meditated”.

Apparently back many decades ago when guys like Proof and Eminem were first getting started, it was regarded that a true MC should freestyle most of their raps, even when in the studio.

By Proof’s skillset, it looks as though that level of dedication paid off. Proof’s freestyles are a mix of clever wordplay, competitive bravado, and just straight up hilarious lines.

Thank You For Reading

Thank you for reading my list of the top 5 freestyle artists in hip hop. If you have never taken a listen to any of these guys, go check them out. And also feel free to check out my own hip hop music, which can be found on the Music tab at the top, or also on the YouTube link posted on the homepage.

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