Making The Music Video | A Romantic Hip-Hop Love Song


My name is Jackson Whalan. I’m a lyricist and music producer who creates eclectic hip-hop with a positive message for society. I’ve been making beats and rapping for decades. I independently release music on a consistent basis and perform as often as possible with a live band. On October 18th, 2019, I released a new song called “Ain’t No Going Back”, along with a music video that was released a week later.

Click below to get the song on your favorite platform


"Ain't No Going Back" is a song that took about four years to finish. Late one night, I was working on the song in the studio when a hard drive crashed suddenly, leading to many of the recorded instruments in the song being lost. This was a devastating moment. Over the course of four years, I reconstructed the song with the same musicians, until eventually it was revived and complete. This song is about romance; it's a love song about the magic of meeting a partner and persevering in a relationship. I’m singing on this song, in addition to rapping which was a new development for me, and a skill that has evolved from from my longstanding focus on being a rapper and producer. Award-winning songwriter Robby Baier (Great Barrington, MA) played bass and helped with the lyrics for “Ain’t No Going Back”. Ian Evans (Housatonic, MA), played piano and synths on the song, while I made the beat and added additional production. The song was mixed by Alex Vasquez of Deep Red, LLC (New Marlborough, MA) and was mastered by Bob Macchiochi at Subvert Central Mastering (United Kingdom).



I collaborated on the music video for “Ain’t No Going Back” with my girlfriend, Amy Inglis (Avida Love Photography) who helped come up with a shot list, starred in the video, and did all of the filming. We made this music video without a budget over the course of a week, using a Canon Mark III, a Zhiyun Crane 2, and minimal lighting. Before we made the video, we did a deep dive into Youtube, searching for love song music videos from artists we both like. We got inspiration from “All of Me” by John Legend, “My Favorite Part” by Mac Miller featuring Ariana Grande, “LOVE.” by Kendrick Lamar featuring Zacari, and a few others. I personally learned a lot about making videos on no budget from doing Spike Lee’s Masterclass.


  • Rapping in front of white backdrop

  • Amy in front of black backdrop dancing with a strobe light (overlaid with film contact sheet)

  • Both of us in front of black backdrop with a strobe light, embracing each other.

  • Rapping in the car, driving shot

  • Church rapping shot

  • Walking away down the hill (super-imposed)

  • B roll footage of Amy doing photography

  • Amy watching my church rapping shot on Instagram Stories

  • Rapping by the river during sunset


We had plenty of other shots in mind that we wrote down. We tried some that didn’t work out, and some we just couldn’t get in the end. We got a lot of footage that we didn’t end up using. I sat down to edit the video on Final Cut Pro, got all of the footage ready, and then decided that we needed to go back out and shoot more.

ADVICE FOR MUSICIANS MAKING DIY MUSIC VIDEOS: Always brainstorm, get inspired, and take your time making a shot list. Always make one. Even if you don’t get all of the shots you imagine, or you end up doing shots that weren’t on the list, you will thank yourself later for creating a framework and charting your course. Spontaneity is inevitable, but it’s important to be clear about what you’re going for before filming. If you wing it, that will come across in the final product.

We ran around The Berkshires, MA, checking off different locations from our list until we had more than a sufficient amount of video footage. I edited for for a few days non-stop. We made most of the music video black and white because we liked the vibe that it created. I learned how to do selective color (or color isolation effect) by watching this great instructional video here. I wear a lot of hats in my music career, and I have to admit, making music videos is very fun.

PRO TIP: I uploaded a sneak peak to my Tik Tok page and it ended up getting thousands of views overnight. I recommend that musicians start using this platform, and my man Gary Vee would agree…

I put out new music regularly, and the best way to hear my new music is by following on Spotify.

If you’ve made it this far, thank you for reading the whole blog post! Please listen to my music and if you like what you hear, follow on socials and subscribe to the mailing list below for more music and valuables.


"Dear Mr. President" Song & Video - A Scathing Indictment


Emcee/Producer Jackson Whalan continues his prolific run of eclectic hip-hop releases with the blistering single “Dear Mr. President”, a furious-yet-focused response to a culture in crisis, and a scathing indictment of the so-called leader of the free world.

(click on your favorite)

Riding the high of several recent Jackson Whalan Live Band releases, and a smattering of successful concerts with the group, the rapper returns with a vengeance, steadily pushing the status quo with thought-provoking subject matter. The evolution continues with the October 4th, 2019 release of “Dear Mr. President”, a bold example of the Massachusetts-based wordsmith using his voice to affect change, redirecting his own attention, and ours, at once inward and towards the nation’s capital.

The track is right on time with regard to current cultural events and the upcoming 2020 presidential election, but aesthetically it’s a throwback to a simpler time in hip-hop. A smoky piano chop dances atop boom-bap drums, a combo that calls back to mid-90’s era DJ Premier or classic Boot Camp Clik, Jackson settles in to speak his mind, he gets serious and leaps into the verses with a patient, golden-era cadence. The longtime activist is just motivated and exasperated, while the song’s title is intentionally direct, the lyrics reveal a nuanced style of messaging that communicates clearly but does not come off preachy. 

“It’s what I would hope to say if I was in the room with him. It’s been very tough for me to put how I feel into words regarding the current administration, but the mood of the beat really prompted the character of my rhymes and the subject matter; the anger that’s been welling up inside of me just kind emerged, and I allowed it to go there.” Jackson Whalan

Press photo by Avida Love Photography

Press photo by Avida Love Photography

“Dear Mr. President’s” first verse finds Whalan addressing the culture at large with observatory metaphors galore, while the second verse is a more direct breakdown of how this particular president is swimming in his own narcissism and selling lies to the citizens while climate change and communities continue in despair. The sum of these parts is this sign of the times, and Whalan delivers an artistic statement that is cut from the same cloth as politically-charged hip-hop heroes like Public Enemy, Dead Prez, X-Clan, and Immortal Technique. 

“In a more direct sense, the lyrics are meant to shed light on climate change, misinformation, freedom of speech, immigration, and how narcissism prevents a leader from dealing with any of these issues.” explains Whalan 

Jackson Whalan co-produced “Dear Mr. President” with longtime collaborative partner Ian Evans, the keyboardist of Jackson Whalan Live Band, and a talented player who’s worked with reggae icons like Barrington Levy and Collie Buddz. The track was mixed by The Arcitype, an accomplished producer in his own right with an impressive resume that cuts across the genre; it was once again mastered by Bob Macchiochi at Subvert Mastering (UK).

Photo at The Bridge Sound & Stage in Cambridge, MA (Avida Love Photography)

Photo at The Bridge Sound & Stage in Cambridge, MA (Avida Love Photography)

Press release written by B. Getz/Upful Life

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The Jackson Whalan Live Band Opens for Talib Kweli on 9/27

On September 27th, Jackson Whalan and his live band will be opening for Talib Kweli at Hawks & Reed Performing Arts Center in Greenfield, MA.

This milestone comes as Jackson Whalan prepares to put out his song “Dear Mr. President”, set to release on October 4th. The lyricist and producer has been working incredibly hard in the studio finishing a large folder of unreleased music to add to his rich catalogue of singles, EPs, and albums. Earlier in the summer, he released his Epic Proportions live band EP, which launched his focus on playing the majority of his shows with a full live ensemble. For this show, Jackson will be joined by musicians from his hometown in The Berkshires, MA: Brandon Lewis on drums, Brian Ross on bass, Ian Evans on keys, Ian Stewart on trumpet, and Tyler Gasek on saxophone, with Jackson on lead vocals and samples.

Doors at 8PM
Jackson Whalan Live Band at 8:30 PM
Followed by Maspyke & Talib Kweli

Hawks & Reed Performing Arts Center
Greenfield, MA 01301


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Jackson Whalan and His Band Bring Live Hip-Hop to "Epic Proportions"

Jackson Whalan and His Band Bring Live Hip-Hop to "Epic Proportions"

Jackson Whalan and His Band Bring Live Hip-Hop to "Epic Proportions". The five song Epic Proportions live band EP drops in full on June 21st. This first single is available on Spotify and SoundCloud, along with an EP Pre-order via Bandcamp. Get it all here.

Successful Live Band Recording Session | New Music & Video Coming Soon!

The Jackson Whalan Live Band recently recorded five songs at Pilot Recording Studios in Housatonic, MA with in-studio video for each song. The project will be released as an EP titled Epic Proportions in the coming months (release date TBA), with a full-on video campaign aimed at getting some bigger shows booked for the six-piece group. On top of this, Michael Wilbur of Moon Hooch showed up to the studio and is featured on vocals and saxophone for one of the songs, “Climate Chaos”.

Fans who join Jackson on Patreon this month will have immediate, exclusive access to the project while it’s still unreleased. The first video is already available to Patrons, so now is the time hop on board and tune in!


Jackson Whalan



Jules Jenssen



Brian Ross


The band went into the studio in the midst of playing Rockwood Music Hall in New York City, Middle East in Cambridge, MA, and Shire Breu-Hous in Dalton, MA. With this three-show northeast run complete, the focus now turns to getting this brand new music and video out. For those who have not been introduced, the band consists of Jackson Whalan on vocals and sample pad, Jules Jenssen on drums, Brian Ross on bass, Ian Evans on keys, Ian Stewart on trumpet, and Tyler Gasek on saxophone. These guys have been playing music together in The Berkshires and beyond for upwards of ten years. Their deep friendship speaks clearly through the music, which has been defined as jazzy hip-hop, jazz fusion, heavy metal rap, soul, funk, conscious lyricism, and so on…


Ian Evans



Ian Stewart &

Tyler Gasek


The next Jackson Whalan Live Band show will be on May 24th at The Barn in Egremont, MA, with an opening set by the JW live band drummer, Jules Jenssen, showcasing his MAD MIDI solo performance. Tickets available here.

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12/29 at The Egremont Barn: Jackson Whalan Live Band

On Saturday, December 29th at 8PM, Jackson Whalan will perform original hip-hop music with his live band at The Egremont Barn in Egremont, MA. Tickets are available here. Amidst frequent touring and consistent music releases over the past few years, a hometown show is a special occasion for Jackson.

The live band formation will include Jules Jenssen on drums, Brian Ross on bass, Ian Evans on keys, Ian Stewart on trumpet, and Tyler Gasek on saxophone. Here is some footage of their recent rehearsals:

In May of 2018 Jackson released his most recent album, Millennial Sound, an exposition of generational angst and a look at current affairs of the world through the lens of classic hip-hop production with a modern flare. He has since released additional music, and is currently based in The Berkshires with a studio space in Housatonic, MA, where he makes beats and records his vocals.

As the year ends, Jackson looks forward. He plans to release a series of singles and music videos in 2019, all of which will culminate into an album. He will continue to tour, strategically so, and is beyond excited about playing with a live band, a change of course from his solo DJ/Producer format of performing. Jackson claims, “the live band creates a huge impact. It’s like the instrumentation is the score, and the lyrics are the movie. I am so fortunate and thankful to have grown up in The Berkshires with such talented musicians who are also close friends. There is something about us all on stage together that can’t be felt if it’s just me spinning my beats. I feel like this band is going to go far.”

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