Best Five Fingers Of Death Freestyles

Written on May 1, 2020

When talking about the best five fingers of death freestyles, you have to mention Sway Calloway and Heather B. Gardner. They’re both champions to the hip hop community and use their platform to give artists the opportunity to get their name out and showcase their skills.

Together, they host the show Sway In The Morning where they have a multitude of guests on to talk about a wide range of topics. The backgrounds of these guests range from rappers, singers, actors, politicians, and even astrophysicists. This show also has one of the most recognizable intros on YouTube, where a bunch of people famous rappers and actors are saying, “Sway”, “Sway”, “Sway”, “In the morning”, “In the morning”, “In the morning”, “Wake yo punk a** up”, “Get that crust out your eyes”.

Another iconic part of the show is the famous five fingers of death. This is where Sway will put the artist to the test with a series of five different beats that each play for about a minute before transitioning into the next, and the artist will freestyle to them. When I say freestyle here, I mean kick a written. MOST rappers that perform this challenge give us something that was previously written, and that’s expected.

There are only a handful of rappers who went to the show and actually freestyled something off the top of the head, but I’ll get into that later on in this post (those rappers aren’t regular human beings).

You know when the challenge is about to start when you hear Sway build-up and say, “And when you come up here you know where you are, it’s not just SiriusXM, YOU IN THE VALLEY OF THE HYENAS!” Some artists fail this challenge, some do just alright, but some absolutely body these beats. Here are the best Five Fingers of Death freestyles:

5. Grafh

Grafh has one of my favorite flows to listen to. It’s smooth and he just glides over the beats and always injects a good bit of humor into his rhymes. Being a somewhat unknown but highly skilled veteran in the game, his body of work is extensive and you can almost feel the passion for rap as he’s rhyming. He’s appeared on Sway in the morning a handful of times and this time, he dropped a freestyle that landed him at my number five spot.

Standout lines:

I’m a boss, n**** you heard what I said already / Any rapper better than me is dead already / The legendary spirits that are dead and buried / Are hereditary my DNA in the cemetery /

That’s bars.

4. Tory Lanez

I haven’t heard that much of Tory Lanez’s studio music but I’ve heard just about every freestyle he’s put out on Sway and Hot 97. I know what he can bring to the table. Listening to this dude rap, you’d be surprised that he can actually sing too. Tory switches his verses up through these five classic beats seamlessly, without missing a beat (no pun intended).

Standout lines:

Have it looking like a dinner when I’m drivin’ / My d*** like my grip, it gets bigger when I slide in / 45th skippin’ like flipper on the glide in / Coming through the spot, jewels drippin’ like Poseidon /

3. Papoose

The homie Papoose showed up with a matching blue sweater and stocking hat ready to set the studio on fire. This dude has been rapping for a long time so you know he has a multitude of verses ready to go to whatever beat is thrown at him. That’s important to note here because I feel like he got some of the most difficult beats to rhyme over compared to other artists. He killed this regardless. Love live Papoose man.

Standout lines:

I rock a watch with large stones / Do it for the love of hip hop like mom Jones / My rhymes memorized, ya’ll read out of ya’ll phones / Just a bunch of dumb n***** with smartphones /

2. Oswin Benjamin

Oswin Benjamin came on Sway in the morning to help promote his new album Godfrey. Not only did he do that, but he also delivered one of the best freestyles I’ve ever heard on Sway in the Morning. His wordplay is ridiculous and he is kicking some serious knowledge during this 10-minute gift he delivered.

Standout lines:

Before the Lox, couldn’t get the P or a Kiss for nothin / When I would kill a mic (Killer Mike) at every show and see low green (Ceelo Green) / This Big Boi would dream to get his family out the Dungeon / Make n***** look up to bars on some bottom bunk s*** /

I couldn’t pick just one, here’s another:

Taking lions out of the jungle, labeling them a threat / In environments you designed to be ruptured / But until my lions learn how to write from they own perspectives / Every story read will be glorifying the hunter /


1. Los

King Los. What more do I need to say? The undisputed champion of freestyling. This one gets my number one spot and is my top 5 five fingers of death freestyle because he’s ACTUALLY FREESTYLING. This is incredible. He’s done this many times on many different shows. This time, in particular, is impressive because Sway is calling out words while Los is rapping and those words get incorporated into the rhyme. I’m not convinced Los is a human being. I think he’s a cyborg that was created in a lab somewhere. True legend right here.

Standout lines:

I don’t really get it, I got two brains in the same mind / I break it down and get two thoughts at the same time /


These are what I think are the best five fingers of death freestyles. I highly recommend you check out Sway’s University on YouTube and thank Sway and Heather B. for all they’re doing for the hip hop community.

I’d be curious to know who you think had the best five fingers of death freestyle.

About the author

I'm not music expert but I know what good hip hop sounds like. I'm just a dude who loves music and feels that non-mainstream hip hop is under-represented and under-appreciated. All thoughts and opinions are my own but I'd love to discuss.

More Lists

See All Lists