The Upful LIFE Podcast – Episode 042 : JACKSON WHALAN (emcee/producer) + Welcome Back Lettuce & D’Angelo

Episode 042 welcomes JACKSON WHALAN, emcee/producer based in the Berkshire mountains of Mass. We met in NorCal about 5 years ago, and he released his latest full-length LP From the Woods in Jan 2021; Whalan’s got a huge collab on the way with the legendary Blastmaster himself, KRS-ONE. Jackson also helped inspire me to start this podcast when we did a live onstage Q&A in Nevada City, CA back in 2017.

  • @4:00 – Welcome Back LETT & ‘Mr. Yancey’ live in Denver 
  • @10:00 – Jackson Whalan intro, @15:00 JW interview  / @1hr 50min S.N.A.G. by Jackson Whalan 

Our 90-min conversation touches on JW’s colorful journey, from humble rural environs to the NYC underground, ashram across the world to a pot farm in Grass Valley, Cali. Other rabbit holes: being white in hip-hop, surviving as an independent artist, using social media to your promotional advantage, and a discussion that unpacks our respective brushes with the law. We finish up with an exciting career development involving the great KRS-ONE.

About Jackson Whalan:

On the western edge of Massachusetts, there were very few examples of hip-hop artists from his rural hometown, but the music made its way into his life when he found CDs that belonged his older brother. When Jackson discovered the power of hip-hop, he was waking up to issues of race, class, politics, human rights and climate change. His music soon became the vehicle for addressing injustices and inspiring people.

In 2012, college studies took Jackson to India and an eco-village, Auroville. In the U.S., he studied turntablism at The New School with DJ Rob Swift; he graduated in 2013 with a B.A. in music. Jackson began releasing and performing under his own name in 2014, with the release of “S.N.A.G. (Sensitive New Age Guy)”. Other releases followed: Raptivism (2015), “Cradle” (feat. Qwill), 2016, and Souled Out EP (2016). Jackson opened for Moon Hooch for over 50 dates during 2016-17.  Jackson is an accomplished hip-hop/electronic producer as well, an Ableton educator, and makes himself available to other independent artists in a variety of professional, marketing, collaborative and artistic capacities.


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In 2019-2020, Jackson released singles and instrumentals every month for a full year, working closely with his co-producer and keyboardist Ian Evans. Tracks include “G.T.F.O.H.” (feat. Myka 9), “BIG FVCTS”, “The Long Game”, and a cover of John Lennon’s “Gimme Some Truth”. Latest LP From the Woods dropped Jan. 2021. KRS-ONE collaboration is on deck, as you hear at the end of our convo. STREAM From the Woods HERE

Vibe Junkie JAMZ

Roy Hargrove feat. D’Angelo “Bullshit” (2006)

The Violinaires “The Upper Way” (1972)

music played: Jay-Z “Open Letter”  — Jackson Whalan “From the Woods” BIG FVCTS” “Cuz I’m Dope” “Music is the Drug” “SNAG”  — & Soulquarians + Femi Kuti + Macy Gray “Water No Get Enemy”


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Listen on Spotify! 

Theme Song: Mazel Tov by CALVIN VALENTINE