Stretch and Bobbito freestyle favourites

With the anniversary of the tragic death of Big L this week, we thought it would be an ideal moment to dig into the archive and rank our favourite Stretch and Bobbito 89.9 WKCR radio show freestyles. Big L famously ripped it up on numerous occasions by himself as well as with Jay Z and Children of the Corn. The influence of Stretch and Bobbito cannot be understated and if you haven't delved into that, their documentary "Stretch and Bobbito: Radio that changed lives" is a great starting point! Starting at 1am the show featured, over numerous years, a whose who of '90's rappers. It was a beautiful thing.

But we are here to rank our favourites, annoyingly a complete archive is not online in one place so we have stuck to ones we can actually access online...

#5 Kool G Rap and MF Grimm


Such a lovely rap pairing for Stretch and Bobbito's 5th anniversary show, the final two verses are absolutely banging from 7:37 onward. MF Grimm is one of the forgotten MC's of this period but should not be slept on. If you are interested in digging deeper into his career, his biography is an award winning graphic novel that we thoroughly recommend!

#4 Masta Ace Inc


We might be biased here as Masta Ace is one of Stacks favourite rappers but it is his patience on his verses that really gives it so much punch. He extends through the beat, dropping the flow and picking it up again. Even on this, he feels like a veteran. Making his own sound effects Masta Ace just smashes this with some effortless style. If you like this, check out his 2001 album Disposable Arts which is seriously underrated.

#3 Das EFX


Top 3 and even now we feel like we have left a bunch out but this Das EFX freestyle could not be disregarded. Das EFX have this sing-song-nursery-rhyme-style that disguises the complicated rhyme structures that should not be overlooked. This freestyle set off a 2 hour listening session to their back catalogue in the office.

#2 Souls of Mischief and Kurious


The beat really helps create a contrast in your mind which highlights how much fun they are having with this freestyle, it feels almost dangerous, like they are treading a tightrope where at any moment they might somehow drop the flow or the beat or lose the rhyme but it never happens an it is that ability coupled with the joy of the whole thing that makes this our number 2...

#1 Big L '98


It was always going to happen. Big L drops some absolute fire on this from his hatred of the Knicks to that Beavis and Butthead line to "Your running with boys, I'm running with men..." part that just smashes...RIP Big L. Hopefully, like us, you are going to be bouncing to "Lifestylez ov da Poor and Dangerous" on repeat in memory of Harlem's finest

This is our personal list, to be honest we have left so many on the cutting room floor here so if this has peaked your appetite we actually compiled a YouTube playlist of every single one we could find here. Some favourites that did not make the cut...Mad Skillz, Big L and Jay Z, Jay Z and Jae, All the Black Moon stuff (so good could not pick a favourite), Wu Tang, Biggie, AZ, Wordsworth, Big Pun, Blackstar, and much. 

Stretch and Bobbito are still doing their shit, their show moved from NPR over to Apple podcasts and they did an excellent interview with Talib Kweli here if you have a spare two hours...