Top 20 Best Sway in the Morning Freestyles Prior to 2020 Sway and Shade 45 are a must-stop for lyricists, and these MCs showed and proved

Sway Calloway is an icon in hip-hop culture, from his Wake Up Show with King Tech to MTV VJ and Shade45 Dj on SiriusXM. He’s been pushing the best (and worst) rappers in the game to their lyrical limits for decades now. As we approach 2020, here are some classic freestyles from Sway in the Morning.

20. Token

Token clearly idolized Eminem in his teens, and thought dissing him would be cool. It’s a new world though, and he’s got a lot to say about being labeled as a YouTube rapper or any other pigeonholing label by the time he comes back in his 20s.

19. Lecrae

Lecrae is a Christian rapper, but he’s got bars, and he doesn’t want to be pigeonholed either. He comes armed with stories, punchlines, and hard rhymes.

18. Tory Lanez

Tory Lanez spends a lot of time on Sway’s airwaves. This Canadian singer, rapper, and producer is a far cry from Drake in a lot of ways. Check out a few of his fire freestyles.

17. Vic Mensa

Vic Mensa is a young Chicago rapper who crosses musical borders into punk rock, repping the anti-establishment of rap.



16. ScHoolBoy Q

ScHoolBoy Q comes correct when he raps over the 5 Fingers of Death.

15. Chance the Rapper

Chance the Rapper is always interesting to watch live. He breaks boundaries in every way, and his second appearance with ASAP Ferg and his brother brings some fire too.

14. Boogie

Boogie is one of the more interesting artists under Shady Records imprint, and it’s unfortunate that people confuse him with Boogie wit da Hoodie.

13. Brother Ali

Brother Ali’s trademark sing-rap style works great here, even if he’s spitting a few verses we’ve already heard (or would soon after) on his albums.

12. Damian Lilard

Portland Trail Blazer Damian Lillard is one of those basketball player/rappers we can actually (sorta) respect, thanks to a pair of fire freestyles.

11. Mistah F.A.B.

Mistah Fab is a frequent guest on Sway who always has something to say, whether it’s on wax or not.


10. Cyhi the Prynce

Cyhi the Prynce is a Georgia-based rapper who stops by Sway whenever he’s up north. Each time, you know he’s bringing fire.


9. Dizzee Rascal

Dizze Rascal is the 2Pac of England, which is pretty much all coast and a ton of poverty and class equality issues. He brings his unique street style across the bond for Sway on SiriusXM.

8. Meek Mill

Meek Mill kills the five fingers of death, rapping for 10 minutes straight, even going a cappella. He had a lot to say about his now iconic life.

7. Joey Bada$$

Joey Badass is an underrated rapper who stopped by Sway in the Morning to destroy the Five Fingers of Death with an epic freestyle.

6. Childish Gambino

Childish Gambino has not one, but two classic freestyles, one of which was done completely in character.

5. Tech N9ne

Tech N9ne came to the public consciousness through his Sway & Tech Wake Up Show verse with Eminem and others. It’s only fitting that he uses the platform to promote all his up-and-coming Strange Music artists.


4. Papoose

Every time Papoose is on the mic, you know it’s going to be fire. He’s been under the radar, yet deeply involved in the rap game for 20 years now, and this freestyle is one of the reasons he’s a legend.

3. Lil Dicky

Lil Dicky is a different kind of rapper, but he still has talent. He stops by Sway in the Morning twice to drop some hilarious freestyles with great punchlines. Time will tell if he can sustain a career in the 2020s.

2. Logic

Logic kills the five fingers of death in his appearance, taking swipes at everyone in the game.

1. King Los

King Los is a Baltimore MC who rode with Bad Boy before landing on RCA. He’s a God MC who rocks the mic for five beats starting with K.R.S. One as a warm up before Sway starts throwing out “words” to rhyme, most of which are sentences.


Dr. Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer. You can find his work in Cracked, High Times, HuffPost, Lifewire, Forbes, Fast Company, and dozens of other places, although much of it is no longer under his name. Dr. Penny loves annoying fake media.

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