Alright – so today we’ve got the honor of introducing you to Bailey Funk. We think you’ll enjoy our conversation, we’ve shared it below.

Bailey, thanks for taking the time to share your stories with us today Can you talk to us about how you learned to do what you do?

I’ve been creating art for as long as I can remember, thanks to my father. He was a true freelance artist in every sense and also taught continuing education art classes. Growing up in Milwaukee, every single school I went to had a strong focus on the arts and not much else. From an early age, I felt a natural passion for art, and he nurtured that by teaching me different techniques and styles over the years—almost like private lessons—long before I ever attended art school.

Knowing what I know now, I wish I had broken out of my shell much sooner and taken more risks in my 20s—especially when it came to choosing art shows and pursuing opportunities I passed on because I doubted my skills compared to other artists.

I honestly believe that all of the skills I was taught were essential, especially with the direction art is heading today. I’ll always be grateful for the techniques I learned along the way, before the world shifted so heavily toward digital art.

Bailey, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Ever since I could remember, I wanted to be like my father. He created art my entire life, so becoming a painter myself felt like a natural choice. When I got into Columbia College Chicago, I finally had the opportunity to connect with like-minded artists who looked like me, many of them later helped showcase my work at their events as well as shows around the city.

After my short time in college, I did move to New York and then to Texas, all while trying to figure myself out— but always searching for where I belong, still maintaining my artistry and always trying to make something shake.

When life came at me fast, I found creative ways to keep my head above water —making color prints at Kinko’s and selling them online for $20 a pop. More than once, I was able to pay my rent this way, and that resilience alone is something I’m truly proud of.

I like to think what sets me apart from other artists is my raw approach to color and contrast. I always start from black and build with bold colors choices, which make for a bright and vivid painting— proving something beautiful can always come from dark places.

Over the years I’ve come to realize that commission work can be some of the hardest art to create. Recently, I heard another artist say that we need to practice using the word “no” when it comes to certain commissions, and I couldn’t agree more. While some projects feel rewarding and a part of what we want to share with the world, others can become stressful and filled with endless edits and excessive requests—all while undervaluing the fact that our time, as artists, is money too.

Despite the art world shifting more and more toward the digital form, I’m proud that my work has stood the test of time as long as it has. I don’t know what the future looks like, but I believe in the mastery of my technique and no matter how advanced digital art becomes, I hope my work will continue to shine in its own right.

Recently I’ve had some artistic blocks, so I am currently focusing on my podcast called Face Value with my best friend as a way to aid my insatiable hunger for creativity. Our mission is to create a space where black ALT authenticity thrives, perspectives collide, and the city’s creative spirit is elevated. Through honest conversations and fearless exploration, we hope to connect the underground to the mainstream, honoring Chicago’s legacy while taking part in the path of its future musicians and artists.

Is there mission driving your creative journey?

I like to think my mission in life is to remind people of the power of compassion. James Baldwin once said, “The world is held together by the love and compassion of a very few people.” I truly feel like one of those people. I’ve always carried deep empathy, and while the world isn’t always kind to people like me, my art gives me a way to express that without it feeling so overwhelmed all the time.

It doesn’t always have to be about pain and struggle. Sometimes, art can open doors to conversations that words alone cannot. Not everyone is ready to talk about things like acceptance and healing, but I’ve found that my art can be a bridge to those kinds of thoughts. At the end of the day, the day gotta end and I hope my art and platform challenge people to rethink their assumptions about others and about themselves, because if we don’t learn to grow together, we always risk falling apart.

What do you find most rewarding about being a creative?

I think the most rewarding part of being an artist is knowing that, even in a saturated market, I still feel like an anomaly—like I have something truly unique to offer. Art has always given me a sense of purpose and validation in a way nothing else has.

Growing up, I struggled with feeling like I had to prove myself, and constantly questioning whether I was good enough. But with art, it was always different. People have always shown respect for my work, and that recognition has been a huge boost to my confidence, even to this day.

Besides that, painting has always been a way of processing my emotions—something I haven’t always been great at doing. It’s been cathartic at times yet therapeutic, but has forever allowed me to express things I might not have been able to put into words.

Contact Info:

• Website: https://bfunky.us
• Instagram: @baileys.funky
• Youtube: Face Value Podcast
• Other: https://facevaluepodcast.com