Artist in Residence: In Conversation with Leonard Baby
At The Shelborne by Proper, we believe that travel, art, and place share a unique ability to shape memory. This season, we welcomed our inaugural Artist in Residence, New York-based artist Leonard Baby, for an extended stay immersed in the atmosphere, architecture, and enduring magic of Miami Beach.
Known for his deeply personal and cinematic paintings, Leonard spent his residency drawing inspiration from the rhythms of the property and the city beyond, creating two original works during his stay. As part of the residency, Leonard also hosted two evenings of intimate painting workshops, welcoming hotel guests, members, and the local community into his creative practice. Rooted in observation, emotion, and storytelling, the sessions offered participants a rare opportunity to engage directly with Leonard’s artistic process while fostering moments of creativity, connection, and shared expression.
We sat down with Leonard to reflect on his artistic practice, the creative process behind the works created during his residency, and the moments that made his time at The Shelborne unforgettable.
For Leonard, the residency became an exploration of light, leisure, memory, and the quiet rituals that define a place. Through painting, conversation, and observation, his time at The Shelborne captured a distinctly Miami Beach feeling: fleeting, romantic, and impossible to fully hold onto.
For those discovering your work for the first time, how would you describe your artistic practice?
I mostly paint. Occasionally sculpture or performance. It’s all about my biggest obsessions, greatest fears, and maddest loves.
When did you first realize that becoming an artist was your path?
As early as I can remember. I’m not qualified for much else, so I really hope I can keep it up.
What drew you to participate in an artist residency at The Shelborne by Proper?
I love the hotel. I love Miami. I live for the beach.
How would you describe your artistic style in three words?
Earnest. Pensive. Ridiculous.
How did spending a week in Miami Beach influence your creative process?
The light is impossible. I spent the week trying to catch it.
Was there a particular space, moment, or detail at The Shelborne that inspired you most?
The diving board.
What does a typical day in your studio, or during a residency, look like?
Coffee, a song I can dance to, then paint until dinner. Sometimes later.
What was your favorite moment from your residency at The Shelborne?
Swimming, sketching in bed, room service, and meeting people. It was all heaven.
Do you begin a piece with a clear vision, or do you allow the work to reveal itself over time?
I always start with a composition, usually a film still. But the painting itself always has a better plan than my own.
What themes, emotions, or ideas are you exploring in your work right now?
Lately, indulgence. Sleeping in. Dancing alone. Staying at the beach too long.
Did teaching others during the painting workshops influence your own perspective as an artist?
Yes. Beginners are much braver than me.
If your artwork had a soundtrack, what would be playing?
It’s always changing, but this week it was The Beach Boys.
His two original works, created during his stay, stand as lasting reflections of that experience and mark the beginning of The Shelborne by Proper’s Artist in Residence program.