lyricist and producer from the woods creating hip-hop from the heart to uplift and inspire listeners around the world.

Jackson Whalan is an American lyricist and producer known for his high-impact rapping, music production, live performance and collaboration. He has independently released over 100 songs, including LPs, EPs, singles and features, while touring extensively, both solo and with a live band.


“Berkshire, Massachusetts-based emcee/producer Jackson Whalan delivers the bangin’, bluesy “From the Woods (Remix)” featuring KRS-One, the hip-hop icon and co-founder of Boogie Down Productions. A studio daydream that manifested into a once-in-a-lifetime opportunity, the cut brings together an iconic pillar and omnipresent voice of hip-hop culture and a promising young artist who is putting his own righteous energy into sound art. The results are nothing short of stunning, as KRS-One brings his inimitable presence and bombastic South Bronx style to the thumpin’ “From the Woods” (Remix)…” – B. Getz via Live for Live Music

Origin Story

Jackson was born and raised in Berkshire County, 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. Inspired at age 11 by The Score by The Fugees, Illmatic by Nas, and other late 90s hip-hop, Jackson forged a path not previously traveled by any white kid from The Berkshires.


When Jackson discovered the power of hip-hop, things were turbulent at home, at school and in the world. He was waking up to issues of race, class, politics, human rights and climate change. His music became the vehicle for addressing injustices and inspiring people.

During middle and high school, local hip-hop artist Regi Wingo (Dominik Omega) schooled Jackson on the five elements of hip-hop. Regi led Jackson into the recording and releasing of multiple mixtapes and albums under the name The Aposoul. As a young teen, he began performing locally.

Through a local youth organization, Railroad Street Youth Project, Jackson was paired up with a mentor, award-winning songwriter Robby Baier. The non-for-profit youth organization catalyzed Jackson’s music with unique opportunities for his artistic development. At age 17, Jackson performed at The U.N. Headquarters in New York City for The International Day of Peace in front of a global audience of youth representatives and Messengers of Peace: Jane Goodall, Elie Wiesel and Michael Douglas.

Education/First BAND

Jackson attended The New School University in New York City, and formed a band, Technicolor Lenses, with his friend Sam Eckstein (Esseks). The duo was later joined by drummer Brandon Lewis and vocalist/percussionist, Carmen Estevez. In 2012, the band won first place in The New School Battle of The Bands, with the prize of studio time at The Bunker Studio in Brooklyn, NY. There, they recorded Eternal Eyes EP (2012) with Grammy-winning engineer John Davis.

In 2012, his college studies took Jackson to India, where he studied Integral Sustainability for a semester at an eco-village, Auroville. There, he created a collection of field recordings that he wove into his music. Back in the U.S., he studied turntablism at The New School with DJ Rob Swift; he graduated from The New School in 2013 with a B.A. in music.

Early Career

Jackson began releasing music and performing under his own name in 2014, and his satirical/comical side emerged 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 on the band’s U.S. tours during 2016-17. Among over 50 dates with Moon Hooch, sold-out shows in Denver, Portland (OR), and Los Angeles were milestones in expanding Jackson’s audience.

Recent History

In 2018 Jackson released the LP Millennial Sound, which includes “Death and the Maiden,” a collaboration with cellist and composer Dave Eggar. They birthed a hybrid genre called “chamber rap”, combining classical music with hip-hop by re-imagining Franz Schubert’s composition of the same title. The album’s intro features a speech by American Pulitzer Prize-winning journalist Chris Hedges. Also featured on the album: Katie Jacoby, Lily Fangz, Honeycomb, Jules Jenssen, Agent 23 and others.
Jackson collaborated on another album in 2018, These Aren’t The Words You’re Looking For, with producer/engineer Ian Stewart. Mr. Lif is featured on the song “Rap City In Da Nile, a collaboration that marked a break-through moment in Jackson’s career.
After touring for five years, Jackson faced a personal crisis that threatened his professional future. Living in northern California, a series of dangerous choices forced a hard reset. Moving back to the Berkshires, he committed to undoing his setbacks and developing a business strategy for long-game success with his music.
Jackson brought together a live band with Jules Jenssen on drums, Brian Ross on bass, Ian Evans on keys, Ian Stewart on trumpet, and Tyler Gasek on saxophone. The band performed regularly at Rockwood Music Hall in New York City and throughout New England, including Hawks & Reed in Greenfield, MA, where they opened for Talib Kweli. Jackson brought the live band to Pilot Recording Studios in Housatonic, MA to film and record the Epic Proportions EP (2019).
Jackson released singles and instrumentals every month for a full year, working closely with his co-producer and keyboardist Ian Evans. His top tracks released in 2019-2020 include “G.T.F.O.H.” (feat. Myka 9), “BIG FVCTS”, “The Long Game”, and a cover of John Lennon’s “Gimme Some Truth”.

EARMILK: Jackson Whalan’s New Single “Whale” is a Pure Display of Indie Jazz Fusion

Live For Live Music: Jackson Whalan Reverse Engineers a Live Hip-Hop Experience with “Epic Proportions” [Single/Video]

Berkshire Edge: Area hip-hop artist Jackson Whalan Explores New Ways of Recording, Collaborating with Music

Current Affairs

COVID-19 halted live performance, so Jackson pivoted to studio recording and releasing more music. In August 2020, he released his instrumental album The Road Ahead, Vol. 1 with Ian Evans. Tracks from the album were added to over 25 popular independent Spotify playlists in the first week of its release. Meanwhile, his music was licensed in ad placements by Harney & Sons, Bluehost, Reebok, Champs, Footlocker, Huawei and Smart Car.
EARMILK: Jackson Whalan Spins his Rap Fable “From the Woods”
Now based in the Berkshires, Jackson’s music production studio is located in Housatonic, MA. His full-length album, From the Woods, was released on January 29th, 2021. Following the album release, he dropped a remix to “From the Woods” featuring hip-hop legend and icon KRS-One.
Live for Live Music PREMIERE: Jackson Whalan Enlists Hip-Hop Icon KRS-One For Blues-Hop Anthem “From The Woods (Remix)”
Jackson remains dedicated to creating hip-hop from the heart to uplift and inspire listeners around the world.
Indie Shuffle: G.T.F.O.H. (feat. Myka 9) [Instrumental]
Toneden: Jackson Whalan Finds New Fans with Toneden
HIP HOP DX: #DXCLUSIVE: Freestyle Fellowship’s Myka 9 and Jackson Whalan Regroup in “G.T.F.O.H.” Video
V13: Jackson Whalan Empowers with his Cover of John Lennon’s “Gimme Some Truth” [Premiere]
Berkshire Eagle: Local Rapper, Producer Jackson Whalan Gives Lennon Anthem “Gimme Some Truth” New Life