Ferrari Sheppard

Every time I considered making a jazz painting, I felt a certain caution. I worried about making something cliché or unserious. Eventually, I became interested in that hesitation itself. Why should depicting an art form as glorious as jazz make me feel that I have to defend the subject?

Blues and jazz have permeated the world so thoroughly that we sometimes treat them as facts of nature, as though they have always existed. They’ve come to signify sophistication, international taste, even regality. But they were invented. African Americans created these forms of expression as tools of survival—as ways to give experience a shape, to communicate, and to sustain life under conditions that denied their humanity.

I began questioning why visual representations of that achievement are so often perceived as performative or as catering to a white gaze. There are conventions worth questioning, but I also wanted to examine the suspicion itself: what happens when anticipating that gaze begins to govern what I feel free to paint?

Round Midnight and All Blues came out of that inquiry. I wanted to approach this world with the freedom and seriousness it deserves, and to give the people within it the fullness of their lives—their invention, intimacy, pleasure, and relationships.

The works are clearly inspired by Miles Davis, but I see Miles less as a musical icon and more as a way of taking up space. To me, he represents the exact opposite of caution—the freedom to trust your own judgment, to change direction, and to occupy space without asking permission.

That connects directly to the hesitation I felt about making these paintings. Miles became a way of thinking through that caution and questioning why I felt it in the first place. That question reaches beyond these two works into my wider practice: how much freedom do you allow yourself when you’re anticipating how others will interpret what you make?

It happened that these works coincided with the centenary of his birth. That gave the project another resonance, but my connection to Miles began with what he represents to me.

My collaborations with Avant Arte have become an extension of my artistic practice. My work moves through different forms: an idea, an original painting, a limited edition print. Each form is finite and unique, with its own presence. I see the editions as another expression of the work, carrying it into new spaces and new relationships.