
Charleston has spent decades collecting art — on the Broad Street galleries, in the French Quarter, at Spoleto Festival USA every May and June — yet the city only legalized tattooing in 2004, so large-scale ink here is still rare and quietly coveted. When Penny Boy travels into the Lowcountry for a guest spot, his award-winning full backs give collectors and art-lovers a canvas worthy of the city's taste.
A closed selection of Penny’s award-winning full backs — see them all & in motion, or view the art gallery.
Because Charleston came late to tattooing — legal only since 2004 — almost no one here is building backs at gallery scale, and that is exactly the gap Penny fills. Penny Boy (Massimiliano Pennella) tattoos one thing only, the back, and does it as well as anyone working today: 100+ international awards and Best in Show. For a city that already lives around its galleries, its antebellum craft and the Spoleto stage, a full back by Penny is art you wear for the rest of your life — planned ahead, taken by application, one client at a time.
Penny doesn't keep a studio in Charleston — he travels in for guest spots, and the Spoleto window (May–June), when the city fills with art, is a natural time to plan one. Nothing is fixed on the calendar: apply with your back concept, and if it's approved his team confirms the Charleston or wider South Carolina session that fits.
There is no price list. A full back is a large, multi-session project, and every quote is custom — issued only after your application has been reviewed and approved.
No. Penny is a destination back artist: he guest-spots in Charleston and across South Carolina by application, taking only a few backs each visit. The back is all he tattoos, and full and half pieces are prioritized.