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Stretch & Bobbito on The Notorious B.I.G., Big L, Jay Z, and That Time Kool Keith Met Michael Jackson

Plus get details on a lost Notorious B.I.G. freestyle from when he was 16 years old, including the lyrics.

That iconic "whooooo!" may finally get the recognition it deserves.

Stretch Armstrong & Bobbito Garcia are the focus of the new documentary film Stretch and Bobbito: Radio That Changed Lives, which digs deep on one of the most important radio shows in the history of hip hop music. Stretch & Bob's late night show ran from 1990-1998 on WKCR and 1996-1999 on Hot 97 in New York City, and introduced audiences to legions of new artists, thereby changing the course of music as we know it. Ask Nas or Jay Z or Eminem or Busta Rhymes or Big Pun or Wu-Tang Clan or Cam'ron or Ma$e, and they'll tell you about either their first or an early appearance on the show and the impact that had. The Notorious B.I.G. knew too, and one of the earliest freestyles ever recorded of the Bed-Stuy legend happened on the show. He was 16 years old. More details on that below.


It is undisputed that Stretch and Bobbito are responsible for a seismic cultural shift in rap music, and as such we talked to the pair from 89Tek9 about some of their early experiences with these artists. Head below for stories on The Notorious B.I.G., MF Doom, Kool Keith with Michael Jackson, Jay Z, Big L with Cam'ron, and much more. Check out the documentary, due on October 22, only on Vimeo on Demand. Pre-order yours.

The Notorious B.I.G. with 50 Grand:

Stretch: So I created a blog many years ago in hopes of getting copies of some of these tapes, including this Biggie tape. I have a really vague recollection of him actually being here though, what he looked like…
Bobbito: I remember, he was wearing an army jacket and was eating in the studio. But that’s all I remember.
Stretch: So we got in contact with 50 Grand to try to find the freestyle that appears in the film. We didn’t know that he had that tape until that week, and when he is handing it to us, that was the moment when we are actually seeing it for the first time. It’s incredible. We didn’t know what we were gonna hear until we put it in that tape deck. That is the first time we heard it, was on camera.

Mumbling and whispering is what I hear
When B.I.G. appears on the scene niggas get scared
I’m not the stick up man
I don’t want the rings on your hand
I don’t understand
When I come through the avenue I must know voodoo
Cause all eyes are on you know who
And my so-called friends beg for ends for me to lend
But this bankroll they won’t spend
Open your eyes and realize
Ain’t no sugar in my tank
Out of all my friends, there’s just one I want to thank
My man Big D taught me a lesson that was great
That good things come to those who wait
And we waited through the suffering and pain
And bitches ride the dick like the A Train
That’s why I flip, keep a burner to my hip
Take a hooker to the crib you know she gotta strip
Stay dipped, take out of state trips
Don’t drink a lot of Hennessy, I only take a sip
I’m not a paper gangster of no sort
I do smoke Newports
When I get stressed I grab my vest
Damn, tried to give you the warning sign
When I said chill I wasn’t saying LL’s rhyme
I was telling ya, not to tear up, cause he will rip up
I’m tellin ya not to erupt
He’s just as corrupt as a DJ should be
50 Grand and I’m the B.I.G.



Stretch: The way we came to know those guys was on one of my trips to California. Dante Ross told me that I needed to check out Domino, and that he was down with Del. So I was out at a conference in the Bay Area and I met up with Domino and within 15 minutes of meeting, I was in a stairwell with him, Souls of Mischief, Snoop who would become known as Extra Prolific, and others, passing blunts and rhyming off the top of the head. It was one of the most incredible spectacles of improvised lyricism that I have ever witnessed. Of course they came to NYC and created as big of a splash there as they did in that stairwell.

Interesting thing is that when they came on the show, they were staying with us at our place in the East Village. Their appearance happened to be at the same time that the Rodney King riots were going on, so to be with those California guys while that was happening in California is a very very indelible memory for me.


Bobbito: Kurious grew up on my block as Jorge Alvarez. I actually gave him the nickname Kurious, offered him a job at Def Jam to be a messenger, and really was sort of the mentor figure to get him into rhyming by introducing him to the art of off the top of the head freestyle. He was really a student of that in the 80s and the 90s, but originally he didn’t want to make a demo, he just wanted to record. So I invited him to be the co-host of the show when we first started, and he was a pivotal figure because he was so nice at rhyming off the top that an artist felt more comfortable doing the same. He was so nice at forestalling and raised the bar so very high. We didn’t get to cover that in the documentary, but we always give him love for creating a high standard for artistry at the station.

Big L

Bobbito: L has an interesting history with us because he premiered on our radio show in 1992 before he was signed. After that, he just sort of had the keys to our door.
Stretch: Well, he was from Harlem and the show was in Harlem, so he would just walk to the show. He came up about about five times. Obviously, the one that’s most renowned is the Big L and Jay Z night, but he also came up one night with eight other MCs called the Children of the Corn. Of course, one of those MCs was Killa Cam and another was Mase, then Murder Mase. McGruff got a deal with MCA eventually too. So he brought four artists to our show that later got major label deals.


Jay Z

Bobbito: We knew who he was through his work with the Originators who Stretch was playing on the air. But we really didn’t work with him until 1995. People always listen to and think about Jay’s appearance with Big L, but he came up to the show three or four times and those other moments were phenomenal.

MF Doom

Bobbito: So Doom traces back to his days with KMD. He was already signed to Elektra when he came on our show, though that didn’t last long after the controversy due to the Black Bastards artwork. So in 1995, Kurious was responsible with connecting Doom back to me. So Doom resurfaced and I played the demos of “Hey!” and “Deadbent” before they were released as a twelve inch on my label Fondle ‘Em Records. I’m so proud of what he’s done with his career.

Talib Kweli

Bobbito: Kweli came up in 1995 with as part of a session with Tash from the Alkaholiks. I remember writing down his name phonetically and years later when he came up with Reflection Eternal, I remember going back through the guest log and saying to myself “oh this is the same dude that came to our show years ago.”

Kool Keith

Stretch: The first time I ever went to California was in 1994. Kut Master Kurt, who was working with Keith at the time, picked us up in LA at the airport with Keith. We were hungry so we all decided to go to IHOP (I wasn’t vegan then), but Keith wanted to go up to Sunset first to show us the hookers. So we did, and of course he was being crazy to hookers on the street.

Finally we got to IHOP and were eating and Michael Jackson shows up. He didn’t seem to be with any friends, just a bunch of security guards wearing suits and sunglasses. He didn’t actually come in, he was just sort of standing in the vestibule with all of his guards, but Keith saw him and said he was going to talk to him. So of course we were like “what is going to happen???” but he talked to him and came back. So our first introduction to Kool Keith was Los Angeles, hookers, spandex, Michael Jackson, and IHOP.

Fred Pessaro owns several cassette copies of the Stretch & Bobbito show. Operation: Doomsday and The Juggaknots LP are some of his favorite records.. He's on twitter.