For over 15 years, Funkmaster Flex’s Hot 97 freestyle segment has and continues to be a hip hop tradition. Sometimes used as a proving ground for new artists or as a platform to air grievance, but usually to just showcase lyrical ability. There have been hours upon hours of freestyles of everyone from a pubescent Juelz Santana to the most successful rapper ever, Eminem.

Here is the shortlist of the five best freestyles on the Funkmaster Flex radio show.

#5 – The Lox  (2001)

“Jada come through controlling the Porsche/
Haters shaking like Ali holding the torch.
Walk with me, D-Block, you heard Sheek/
Still sold more than P. Diddy my 1st week.” – Jadakiss

The Lox were the new generation of New York hip hop back in 2001 with Jadakiss’ Kiss The Game Goodbye album climbing the charts. While all three delivered murderous quips, it was Jadakiss’ patent gravelly-voiced thick flow that hit the hardest.

#4 – Canibus, DMX & Noreaga (1998)

“Verbally murdering you thoroughly without effort/
I get drug tested before I can rhyme on a record/
Remarkable specimen with an audible weapon/
Processing lyrics in less than 1/100th of a second.” – Canibus

1998 was a year of rap supremacy purgatory. Notorious B.I.G. and Tupac had recently passed and Hip Hop was being ushered into the Shiny Suit era. But it is hard to deny that in 1998, that Noreaga, Canibus and DMX were on the short list of rawest lyricist in hip hop at the time. Here they blend their three styles for one epic freestyle session on Funk Flex’s radio show. Not enough space to fit all the quotables.

#3 – Slaughterhosue  (2012)

“You add Eminem our hits are the hardest/
Turn DJs to MMA fighters when they Mix Marshall Artists” – Crooked I

Slaughterhouse is a Voltron-like supergroup formed under a shared appreciation for high level lyricism and they had no shortage of that on Funkmaster Flex’s show in 2012. While promoting Welcome To Our House, their major label debut album on Shady Records, the venomous lyricists exhibited their best promotional tool: BARS!

#2 – G-Unit (2003)

“I heard Irv tried to sign Shyne so I aint got no love for him/
Tell him 50 said he’s soft, he won’t shoot up the club again.” – 50 Cent

No one, in the history of hip hop has ever thrived off of blatantly dissing rappers than 50 Cent and 2003 was his apex. Coming off the meteoric success of Get Rich Or Die Tryin’, Mr. Jackson with Lloyd Banks and Young Buck(Tony Yayo was incarcerated at the time) used Funkmaster Flex’s radio show to flex their muscles(no pun intended) and send warning shots to the industry. 50 was so ferocious that even Funkmaster Flex had to stop the freestyle to play Farrakahn and plead with him to play nice. With Shyne’s recent conversion to Judaism it’s almost safe to say 50’s “he wont shoot up the club again” line has turned from mockery to prophecy.

#1 – Jay-Z  (2006)

“Hmm, media meddles, n##### sue you you settle
Every step you take they remind you, you ghetto
So it’s tough being Bobby Brown
To be Bobby then, you gotta be Bobby now”

It’s 2006. Jay-Z is weeks away from releasing his comeback album Kingdom Come and decides to stop by Funkmaster Flex’s show to, essentially, shut down New York City for an hour. Most of these lyrics ended up on subsequent releases (“Corporate Takeover” and “Most Kingz”) but that does not take away from how Young Hova demolishes his Watch The Throne little brother Kanye’s Grammy Family beat. When Hov’s in the zone there are a handful of rappers that can ever match him.