When Hip-Hop fans think of freestyling, the first thing that comes to mind are infamous rap battles like The Bridge Wars, that day when Nas Ethered Jay-Z and when LL Cool J made Cannibus seemingly disappear into thin air.

But true hip-hop heads will tell you that freestyling is an art form all its own. Nobody writes down their rhymes and memorizes them. Dope freestylers are able to create rhymes off the dome — looking at audience members in a club and creating rhymes from what they’re wearing, sizing people up, rhyming about trivial and deep topics, wrestling words, images, metaphors and analogies straight out of thin air.

To honor the freestyle movement, Verizon, 300 Entertainment, Kevin Liles and London on da Track have partnered to find the nation’s best freestyle lyricist with the launch of the #Freestyle50 challenge. The national competition will award seven aspiring artists the gig of a lifetime as opening acts across upcoming 300 Entertainment’s artist tours. They will then compete in a live, freestyle cypher event in Atlanta for a chance to win the grand prize of a single deal with 300 Entertainment and a cash prize of $10,000. 

"Free styling is like when jazz musicians get together and play--like a jam session," said Harlem native Michael Gonzales. "It can be informal or at a club. Most of the best freestyles I've heard were in people's apartments, sitting on a car, in the lunchroom or in the staircase of some building. That's how people in the hood did it."

"We all know dope ass rappers that never got a record contract," continued Gonzales. "His thing was being the best on the block. It's a way of perfecting your craft before they even tried to become a professional."

It's something you can't teach, as critics of Drake will tell you. You just have to have it. But not every great freestyler can transfer their skills to mainstream success. Gonzales remembers two of the best freestylers he ever heard -- Paula Perry who lived in Fort Greene projects and Supernatural never attained the commercial success that some of the rappers of their time period did.

Supernatural was signed, but his label didn't feel like he had a sellable product, so no record ever came out. 

Queens native writer Mark Skillz, attributes talented freestylers not getting record deals to the formula of records that was popularized by Bad Boy Records. 

"What Puffy and these guys did to change the game is they brought in songwriting, structured songwriting. Hooks and choruses. Freestyling appealed to men, songs appealed to women," said Skillz.

Skillz, who moved to the Bay Area, remembers two college shows that helped to bring freestyling to the forefront: the Stretch and Bobbito show in New York and Sway and King Tech's Wake Up Show in the Bay Area. 


"The best part was you could record it and rewind and be able to play it again."

Skillz says some of the best freestylists he's heard were: Kool Moe Dee vs. Busy Bee, Craig G. from the Juice Crew, Kool Keith from Ultramagnetic MC's and King Sun. He says he heard a young Jay-Z freestyle on the radio, but later learned that he was kicking the same "freestyle" --the song "Can I Get Open"--with the group Original Flavor in other venues. That's a purist freestylers no-no.

"To be a good freestylist you have to be able to do it spontaneously," said Skillz. "Hitting that punchline at the right moment that is the hallmark of a great freestyler."

"Freestyling is like if I was a trumpet player and Miles asked me to come onstage," said Gonzales. "Could I hold my own with Miles?"

Ten dope freestyles that you need in your life: 

1) Biggie Smalls on Fulton Street as Lil' Dap walks away before Biggie completely takes his manhood


2) LL Cool J and Cannibus: That time Cannibus disappeared into the Bermuda Triangle 


3) Flava in Ya Ear Remix: What would the world be like if Craig Mack had made an album?


4) Supernatural and Craig G.: Maybe the best freestyle battle ever 


5) When Nas ethered the camel cigarette guy


6) Loaded Lux vs. Calicoe: That time Calicoe got that work from Loaded Lux who predicted his opponent's defeat by coming out with a funeral party onto the stage.


7) Childish Gambino: What can't this guy do?


8) Sway in the Morning: Shia Labeouf When Disney actors get in the freestyle game


9) The Breakfast Club: The Game: You have to come correct on The Breakfast Club


10) Eminem:If you haven't seen 8 Mile, watch this.


Trivia: what movie was freestyler and Oakland rapper Saafir in? (Answer: He was cousin Harold in Menace II Society)