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Isaac Castor – Dear Ann

Isaac Castor - Dear Ann
Isaac Castor - Dear Ann
Isaac Castor – Dear Ann



Discuss your personality.
Down-to-earth 22-year-old, soon-to-be college graduate that has been passionate about all genres of music and artistic expression since I can remember.


Brief us about you as a musician.
I’m 22 years old now, but I first started making a name for myself at the age of 15 under the moniker Gameboi. In that span of time, I’ve been featured on major media outlets such as XXL Magazine and NPR, and I have collaborated with artists such as Boldy James, Statik Selektah, Jon Connor, Antwaun Stanley (lead vocalist on many of Vulfpeck’s hits) and Rapper Big Pooh. My upcoming album, “Old Soul”, is due for release in early 2018 and includes production from DaG, Hir-O, StewRat, and PEEKABOO.


Go into details on what has changed in your life for choosing music as a career.
In 2009, I began attending a weekly emcee workshop at an Ann Arbor teen center called The Neutral Zone. After performing at numerous Neutral Zone concerts and establishing a fellowship with my peers in the emcee program, I released my first official project under the name Gameboi, 2010’s “The Posterchild”.
“The Posterchild” helped me to establish myself as a force within the Ann Arbor rap scene. It propelled me into radio appearances and live performances at venues around the state, including an opening slot for Mac Miller’s sold-out Ann Arbor tour date. In 2011, I released the EP “Freshman Of The Year”. It was produced primarily by Astronote (known for producing Kendrick Lamar’s “Untitled 03”) and assisted heavily by the guidance of A-Side Worldwide’s Jackson Perry. The EP’s lead single, “Act Right”, featured rapper Big Pooh of Little Brother and was produced by 14KT. Act Right caught the attention of producer/DJ Statik Selektah, who played the song on Sirius XM’s Shade 45 and tapped me for a feature on his album “Population Control” later that year… after that, I was off and running.


Tell us the benefits and drawbacks of choosing music as a career.
The benefit is being able to move people emotionally with music. You can educate, inspire action, and just create an environment for people to have fun. The drawback is that A&R is at the mercy of social media numbers and labels have drastically cut back on artist development.


Tell us how you will manage fame as an established artist.
Managing fame is all about embracing your fans. If your desire is to maintain a private life away from the stage, there will always be a disconnection with your fan base because they won’t be able to relate to you as a person. I’m sure the media grind can be tiring at times, but keeping in mind that you’re doing it to share more of your life with your fan base will keep your head in the right place.


Elaborate on the storyline of this song.
“Dear Ann” is an ode to my hometown in Michigan, Ann Arbor. The track originally dropped back in May, and it deals with the dilemma of feeling homesick while simultaneously longing for a change of scenery.


Let us know the greatest moment of your music career.
Playing an opening slot for Mac Miller’s sold-out Ann Arbor tour date.


Tell us the highest amount of money you have ever received from your music career and how it happened.
I am featured on an EDM song by producer/DJ Crowd Cntrl called “The Fall” that has over 400,000 plays on Spotify so I’ve made a couple grand and counting.


Discuss your experience pertaining to live performances, gigs, shows, and tours.
I’ve performed with Mac Miller, Pusha-T, Logic, Lil Dicky, Tory Lanez, Joey Bada$$, King Lil G, and Big K.R.I.T among others.


Tell us how you interact with your fans.
Sharing your thoughts/life on social media and performing anywhere at any time… no venue is too small.


Tell us what you will like to change if you have the chance to turn back the hands of time.
I have had a blessed life and wouldn’t want to change it. Just move forward sharing my art.


Tell us the most important people that have boosted your music career and how you met them.
In 2012 I released “Young and Restless”, an album that featured contributions from Jon Connor, Skywlkr, XV, One Be Lo of Binary Star, and Air Dubai among many others. I continued to perform on tour dates of big-time artists such as Pusha-T, Logic, and Joey Bada$$. The following year, I dropped the moniker “Gameboi” and began performing under my given name, Isaac Castor. The world got a chance to know the artist Isaac Castor through my re-introductory single “Heisenberg”, the Jon Connor collaboration entitled “Basics”, and my feature on the title track “Drift” with the runner-up from the “The Voice” Michelle Chamuel and producer Arjun Singh. The Drift EP reached #2 on iTunes Electronic Music charts the week of its release and led to Isaac landing an interview with NPR’s Michigan Radio. Castor and Singh continued to collaborate following the release of “Drift”, and in 2015 they released a collaborative album titled “High Art”. The album featured Mass Appeal Records artist Boldy James and frequent Vulfpeck collaborator, Antwaun Stanley. The release of “High Art” received recognition from XXL Magazine in their monthly unsigned artist feature “The Break”.


Brief us on what you have in mind before considering music as a career.
It’s always been music. I am graduating soon with a marketing degree so I am better able to understand the music biz from the label’s perspective.


Discuss your good and bad experience in life.
I’m only 22, but I’ve seen that addiction can destroy anyone’s life, no matter how rich, beautiful, or powerful you are. I’ve also witnessed how divided this country is with the election of an unqualified candidate into the oval office. I am still utterly disappointed that our nation would vote for someone that lacks the moral compass to lead this country.


Name the artists that have influenced the world.
In the rap game, you have to mention Pac, Jay-Z, Puff, Dre, Snoop. I have collaborated with and/or received co-signs from Obie Trice, Danny Brown, Statik Selektah, Jon Connor, Mayer Hawthorne, Theo Katzman, Michelle Chamuel, Freddie Foxxx aka Bumpy Knuckles, Killah Priest, and Boldy James.


Tell us about your moment of rejection as a musician and how you are able to cope and move on.
The music biz is ultra-competitive so rejection is part of the game. Every “No” makes me want to work harder and hone my craft.


Tell us the most negative comment you have ever received about your music.
That no white kid from the suburbs can rap.


Tell us how to become a famous artist.
You become a famous artist by making great music, defining your brand, and constantly touching your fan base through your performances, interviews, and social media. Your fans need to feel the passion you have for music and you need to bring that to the table every day.


Tell us how you plan to make an impact on society.
I think I can make an impact on society by educating people on addiction and bringing attention to racism as a white rapper.


Elaborate on the recording process of this song.
The jazzy instrumental work is a bit of a step into uncharted territory for the song’s producer, PEEKABOO, who is an up-and-coming electronic artist that happens to be featured on Bassnectar’s soon-to-be-released EP. “Dear Ann” will be included as a track on my forthcoming project, “Old Soul.”




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