Jay Z Blessed Stretch & Bobbito’s Show With 3 Different Freestyles In 1995 (Audio)

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Earlier this week, AFH shared a 1996 three-hour radio show of DJ Stretch Armstrong and Bobbito The Barber’s show (thanks to DJ Eclipse, who spun then and digitized it now). Big L was among the show’s guests, bringing with him Ma$e, Bloodshed, and Killa Cam’ron (as Children Of The Corn).

Prior to that appearance, Big L had brought with him an MC from Brooklyn named Jay Z. While Stretch, Bob, and many record-buying Heads were deeply up on Jay thanks to Jaz-O, Big Daddy Kane, and Original Flavor, Big L helped show J-A-Y’s lethal freestyle abilities, on one of the most important New York City stages for the craft. At a time when Stretch & Bob’s show was a breeding ground for Mobb Deep, Nas, and Non-Phixion, among countless others. Additionally, the show helped veterans like Kool Keith, Pharoahe Monch, and MF DOOM show new styles, and work beyond the record cycle.

That first February 23, 1995 stop showed Big L and Jay Z freestyling together, years before grumblings occurred that Jay would sign the D.I.T.C. MC to Roc-A-Fella. In ’95, the Roc was a grassroots collective. However, in moments like these, the table was setting for Reasonable Doubt.

Jay would return on July 20, 1995. Nearly 20 years ago to tonight, Shawn Carter showcased a flow and style unlike what heads heard alongside Jaz, Kane, or Ski.

Then, on December 7, Jay went for the trifecta, lacing a freestyle to LL Cool J’s “I Shot Ya” beat with that arrogance, street-talk, and smooth style that would captivate audiences throughout the next 10 years, and beyond.


Stretch & Bob’ shared all three 1995 freestyles as a playlist this week, and this is a time capsule back to the transformation that would eventually lead to Jay Z confidently telling all Rap peers to “watch the throne.”

Which of these is best? Who got best back in Feb’ of ’95, Corleone or Hova?

Visit Stretch & Bobbito’s site for many more goodies.

Related: Travel Back To Big L, Cam’ron & Ma$e Freestyling on Stretch & Bobbito in 1996 (Audio)