OG Hosts Stretch & Bobbito Remaster Biggie Smalls' First-Ever Radio Freestyle

Mahlik Campbell

music /
(NO AGENCIES IN UK, FRANCE, GERMANY, HOLLAND, SWEDEN, FINLAND, JAPAN.) Notorious B.I.G. 1995 during Music File Photos 1990's in Los Angeles, California. (Photo by Chris Walter/WireImage)

Before hip-hop fans across the globe became acquainted with The Notorious B.I.G., the Brooklyn rapper was doing all he could to prove his talents on the mic.

A turning point in his career happened on March 5, 1992, at the underground New York City studio of the 'Stretch Armstrong & Bobbito Show,' as a then-19-year-old Biggie dropped his reported first-ever radio freestyle. Yet this rare gem of rap history would be lost for decades until 2015 when OG hosts Stretch Armstrong and Bobbito Garcia were able to recover the two-minute freestyle.

Now, Stretch and Bobbito have connected with The M19s Band for a jazzy remix built around those same bars – complete with an animated music video – simply titled "Biggie Freestyle."

In an interview with HipHopDX, Stretch talked about the process of bringing this nearly forgotten audio clip back to life. "Finally getting our hands on the elusive Biggie ’92 freestyle in 2015 was crazy because we had zero recollection of what it sounded like, what his rhyme was like or what beat I gave him," he said. "We even wondered to ourselves whether the anticipation of waiting 23 years would be so much that if and when we finally got our hands on the recording, we might be let down.

"There were times that artists that went on to be greats didn’t kill it their first time on our show, which in many cases, was their first time on the radio, period. But Biggie absolutely killed it."

According to Stretch, Biggie had also recently been beaten by The Bronx Zu collective during a live demo battle on Stretch and Bobbito's show, so he was extra motivated to "make sure his rep wasn’t tarnished."

"We remembered that the week before he came up, Biggie lost an on-air demo battle, so part of his motivation to coming up the was to exact revenge on the group he lost to, The Bronx Zu, and to make sure his rep wasn’t tarnished," Stretch said. "You can hear it in his freestyle: the determination, the confidence, the flow, all the makings of a future great.

"It’s just too bad that he had a sour feeling around our show because of the circumstances, and it’s too bad he came up so late (like 4 a.m.!) because very few people recorded this historic recording. Luckily, we have it for the world to hear now. Long live B.I.G."

The Notorious B.I.G.'s legacy was further celebrated by the Rock & Roll Hall of Fame during its 2020 induction ceremony broadcast on HBO. Diddy, who signed Biggie to his first major record deal with Bad Boy Records circa 1993, called his former prodigy "the greatest rapper of all-time" in an induction speech. JAY-Z, Nas, Lin-Manuel Miranda and several of B.I.G.'s family members paid tribute as well.

You can stream the full ceremony on HBO Max.