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Magic In Hyde Park: Affirmations in the Magical Tunnel

Magic In Hyde Park: Affirmations in the Magical Tunnel
Chicago-based artist Courtney Jolliff on 53rd St. in Hyde Park, August 2022.

By Courtney Jolliff

I was battling lots of failure and rejection and hadn’t made a sale yet, and started to question – am I talented or just handsome? So, my specific manifestation began to be, “I just want a black woman to buy my artwork with no hidden agendas, intentions, or expectations.” I didn’t want to make a sale spawning from anything but true intrigue for my art. 

Courtney Jolliff was selling his work on 53rd Street near the Hyde Park Records store in 2022.

I didn’t make a sale, but a black young woman alongside another black young woman walked up to me and extended me an invitation to paint at their first “poetry and live painting” event. That was none other than Menae and Modi, owners of Soulful Chicago, a really great mental healing space for the community, including a bookstore and art space.

Before the event, I went on to practice painting a scene from the movie “Love Jones” as I was only a few months into painting, not even being a painter a full year yet, so I wanted to practice painting the piece I was going to be painting live.

I made a set of affirmations around selling my first piece.

Courtney Jolliff at the live-painting event.

And ended up selling to three black women that night, including the “Love Jones” piece! 

Original “Love Jones” painting by Courtney Jolliff.

It led to an art collector loving the “Love Jones” piece and wanting one for themselves and so I was inspired to do an entire collection!

Artist Courtney Jolliff in 2022 with a special “Love Jones” collection of original paintings.

 I took that collection out to Bronzeville, to 45th and Cottage Grove. No one had purchased walking by me as of yet. It was maybe an hour and a half or two hours. I asked, “Hey, Universe, can I just get $25 from someone?”

Next thing you know, someone walked up – a lady named Mary – which I thought was real cool because I associated that name with my Grandma Chicago. And she had a similar kind of spirit as well. She purchased a piece and she only had $25 cash. She wanted to give me more. I told her, “No, I just asked the Universe for twenty-five bucks so that will be enough.”

Courtney was so excited to have sold the painting to Mary, he accidentally held it upside down when taking the selfie.

I was really so happy about that accomplishment, I went all the way over to Hyde Park to pay respects to my Grandma Chicago and tell her the good news.

Around that time, One of the collectors who wanted the “Love Jones” work, she went on to buy at least five more of my pieces. It was really amazing – at that time, I was coming from not selling any pieces to finally having some success. So that energy kind of kept carrying over.

That collector invited me over to the DuSable Museum silent auction where I donated two of my pieces at a discount price, and they both sold for much higher than the price I donated them for. That was really cool because not a lot of artists who donated their work had them sold.

Courtney Jolliff at the DuSable Museum silent auction where two of his paintings were sold.

For me, that was really important because my Uncle Courtney, who I’m named after, he was the DuSable Museum’s creative director. He was self-taught in graphic design, 3D sculpting, web design and in painting as well. So that whole night was surreal for me, really emotional.

Another photo from the DuSable silent auction event.

After that night, I followed my intuition and my spirit in what I like to believe is the universe’s guidance and the ancestors’ guidance. They were telling me to set up in the Magical Tunnel – under Lake Shore Drive near 57th Street – where I took my street signs. 

I paint different street names on these found objects of cardboard. I turn them into small pieces of nature and the thing about them is every street name that I write, I’ve actually experienced some kind of personal joy or success at some point in my life there. 

I’ve lived in Chicago for about 12 years, and I’ve experienced things on the north side, the south side. When I think of creating, in terms of demographics, I think of everyone as part of Chicago. Every person I’ve ever come across – every skin color, every walk of life and faith, so that’s why I have a street name that came from Hyde Park or a street sign from over east.

A patron purchasing two of Courtney Jolliff’s signature Chicago street sign artworks near 39th Street.

By the way, “over east” is Chicago slang for talking about the east side. So you might see “over east” written on one of my street signs or you might see the word “up north” instead of “north side.” A lot of South Siders, we say “up north,” or we might say “we out west” instead of saying “I’m on the west side.” So I put those little Chicago coins and tokens that only a Chicagoan would know.

Showing and selling artworks near “The Magical Tunnel” in Hyde Park.

I’ve seen a lot of success at the magical tunnel. Everyone is walking through that tunnel no matter where they are from. Someone might be walking through the tunnel that’s from the north side or the south side or from Hyde Park, and as soon as they see a street sign, it might strike a memory or a chord.

Another patron near the Magical Tunnel.

This energy kind of keeps going on and going on, and I find art collectors in the magical tunnel. One time we were rained on in the tunnel so that everyone that was out jogging that night or out at the park or at the lake enjoying the lake, they were forced underneath into the tunnel. Me and the guitarist, we were set up outside, so we were forced into the tunnel.

The rain put a lot of strangers all together in the tunnel. We had all ages, we had children, people of all races, all underneath the tunnel just jamming out. He was receiving lots of tips. It kind of forced everyone to look at my artwork, which was awesome, so then I received a few sales as well. So it was great that we were all in the tunnel jamming out together, striking conversations, getting to know one another while enjoying art. It was just amazing that I happened to be the artist that was there.

Another patron who purchased a signature Courtney Jolliff street sign near the Magical Tunnel.
The vibe is normally real harmonious underneath that tunnel. I receive a lot more attention and compliments and praise and I notice how powerful affirmations are. 

I asked for $35 for the piece, but when I got home, I saw the woman who bought it had sent me instead the worth of the painting, because she sent me $500 on Venmo. The energy just surged and I realized I had to paint the picture of the woman holding the piece. She went on to become a sponsor of my first show , great friend, confidant, & guide/teammate. A kindred spirit whom I consider another jewel of the Point of Hyde Park.

It was a surreal moment when I saw the payment – it really did feel like spiritual liberation. I dropped to my knees and I happened to be right in front of my ancestors’ altar so it felt like a huge congratulations, it felt like a huge acknowledgment not just from an art collector but from the ancestors. Like, “We’ve seen all the hard work you’ve done over the years. Don’t you dare give up.” It felt like a huge milestone to reach.

This painting captures artist Courtney Jolliff’s self doubts and a patron’s encouragement to keep pursuing his art.

It felt like no matter what happens tomorrow, I felt like Hyde Park was showing me appreciation. Hyde Park was showing me not just that I’m seen but that I’m valued. That changed my mindset. It gave me much more confidence to assert my worth as an artist moving forward, to not underprice or undervalue my work. And it also inspired me to keep moving and definitely inspired me to have a community art show in summer 2023 because I wanted to give back. And that was amazing.

When I call that tunnel magical, I really mean that tunnel is magical. It is a tunnel that represents for me evolving, healing, thriving, expanding, joy, family, community, art. And it’s like that reminder that it’s kind of like family. I look at family members and life as things are going to happen but if you say that we’re all one, we all are family, then there’s always ways to move forward. Sometimes things happen that can also make us closer and I really do see that happening when I set up in Hyde Park. I don’t see that slowing down.

Grandma Chicago’s portrait in the 57th Street viaduct with the poster for Courtney Jolliff’s 2023 community art show.

My heart, my soul, my mind – it all healed at the moment and I realized what indeed was happening, the duality of life. The part of the world that’s evolving, healing, and thriving and expanding, that exudes joy, family, and community. Of course it’s parts of the world that exude the opposite, events and circumstances that are completely horrid or downright evil, but the gems of the world are working hard to make it a better place and succeeding.