Top 5 Radio Freestyles

A rite of passage in the hip-hop game is the art of the freestyle. These are usually ephemeral moments that used to only be heard about via word of mouth or if you were really lucky, you’d get a bootlegged tape. The best stand the test of time.

Today, many of them live forever on YouTube.

Many gems have been dropped during these sessions and here are my Top 5 favorites:


No. 5: Meek Mill Freestyle DJ Self - Power 105.1

Meek had to show he was more than the most iconic album intro of all time (don’t @ me). Having a #1 album at the time had him feeling like he was on top of the world. This was at a time where radio free his confidence was on a thousand.

Quotable bars:

F—g up commas and tucking them llamas you know how we ridin’ when I’m in the city / Sipping D’usse when I’m f—g with Roc and sipping Ciroc when i’m f—ing with Diddy

No. 4: Jadakiss Freestyle

Top 5 dead or alive. When Jada first said this, many doubted. He spoke his spot in hip-hop history through pure proclamation. Everything great about Jadakiss is on display in this freestyle. His breath control, command of his cadence, and wordplay are all in top form during this session.

Iconic bars:

I tell you this much hip-hop is not dead / change gon’ come just like Barack said / Money, power, respect like the Lox said / You’ll be the man of the house my pops said

No. 3: G-Unit Freestyle on Hot 97 (Part 1)

This is when G-Unit was unstoppable. You could hear people running around their rooms or going wild in their cars when this came out. This was more than a moment, it was a call to arms for the G-Unit army. They put the entire game on notice.

Stank face bars:

Check my resume homie we got A-1 felonies / But N— we stars, you know A-list celebrities / Rap and street stuff, it’s all the same / I realized that when 50 snatched Ja’s chain

That bar alone sent the entire hip-hop world into a frenzy.


No. 2: Black Thought Freestyle Hot 97

The under-appreciated but always respected Black Thought had to remind people why he considered a god-level MC. Don’t sleep on the lead man from hip-hop’s best band. You might learn something too if you listen close enough.

Bars on bars:

Ayo, my new name is 85 X’s / ‘Cause I’m the rap game certified specialist / When I was reckless I was worried ’bout the guest list / I’m helping rappers everywhere fulfill a, death wish.

No. 1: Jay-Z Hot 97 Grammy Family Freestyle

Jay-Z is the GOAT. This freestyle for Flex has some of his best and most thought-provoking bars. The technical skill combined with the message in his words have proven that he often sees 20 steps ahead of everyone else.

Next level bars:

Same sword they knight you they gon' good night you with / Sh.., Thats' only half if they like you / That ain't even the half what they might do / Don't believe me, ask Michael / See Martin, see Malcolm / You see Biggie, see Pac, see success and its outcome / See Jesus, see Judas; see Caesar, see Brutus / See success is like suicide / Suicide, it's a suicide / If you succeed, prepare to be crucified

Honorable Mentions:

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