The Stretch Armstrong Show featuring Bobbito the Barber (WKCR 89.9 FM) - 2/23/95
The night of the legendary Big L and Jay-Z freestyle.
Inside “The Radio Tapes” chapter of Do Remember!, we had the honor of interviewing Bobbito, one-half of the dynamic Stretch Armstrong and Bobbito duo who co-hosted one of the most celebrated rap radio shows in NYC hip-hop history. And as we explore through the interview, tapes of their WKCR shows in the ‘90s were often bootlegged in the streets, until they ultimately partnered with Fat Beats to officially release them.
One of the many reasons Stretch and Bobbito’s tapes were so hot—beyond the fact that they were breaking new records and artists, consistently concocting mixes that mirrored the vibe and flow of a street mixtape, and had hilariously entertaining personalities—is because they were known to have buzzworthy artists in NYC and across the country come up and freestyle live on the air during their shows.
Which brings us to the 2/23/95 tape. Yes, on February 23rd, 1995, Big L and Jay-Z visited the Stretch and Bobbito show together for their now-legendary back-to-back freestyle session. And whether you think L or Jay killed it more, there’s no question that hearing them rap together on the radio live like this—prior to the release of both of their debut albums—is one of the dopest NYC rap radio moments ever captured on cassette.
Here’s Hov and other hip-hop superstars listening back to the freestyle during a clip from the fantastic Stretch and Bob doc Radio That Changed Lives:
In addition to hearing Big L and Jay-Z rap together live, 2/23/95 has lots more to offer. Honestly, any tape of a Stretch and Bob show is a time capsule we should all cherish, but this is particularly a stellar mix of ill hip-hop joints that popped off in the winter of ‘95—from the DJ Premier remix of Showbiz & A.G.’s “Next Level” to Tha Alkaholiks and Diamond D’s bi-coastal collab “The Next Level”—plus a couple blends, and an appearance/freestyle by Cypress Hill affiliates Funkdoobiest.
Enjoy this treasured piece of NYC radio tape history, and check out more on Stretch and Bobbito, Future Flavas with Marley Marl and Pete Rock, and other influential radio DJs and show recordings from NYC’s mixtape golden era inside the pages of Do Remember!
And of course, a big Rest In Peace shoutout to one of the true GOATS of our time—Big L.
Stream 2/23/95 below, and stay tuned for more 50 TAPES posts as we celebrate the release of Do Remember! The Golden Era of NYC Hip-Hop Mixtapes, out now via Rizzoli.
The Stretch Armstrong Show featuring Bobbito the Barber (WKCR 89.9 FM) - 2/23/95