Born in Milan, Paolo Di Benedetto graduated from the Art Institute of Monza, and then graduated from the Faculty of Design at the Politecnico di Milano, choosing to specialize in interior architecture and fittings.
Paolo has always worked as a scenografo, with projects ranging between installations, exhibitions and theatrical productions. In 2002, during university, he began his long-term collaboration with the Piccolo Teatro di Milano, specializing in set design and developing a thesis on the production processes of the fittings in stable theaters of prose. Paolo continues his collaboration with the Piccolo Teatro to these days and still works on the design of sets for major productions and co-productions, together with set designers like Margherita Palli and Marco Rossi, and with directors like Luca Ronconi, Carmelo Rifici, Antonio Latella, Declan Donnellan, Roberto Latini, Damiano Michieletto, Tony Servillo, Federico Tiezzi and Bob Wilson.
Paolo is a also set designer for installations and special events. He collaborated as assistant for the set designer Marco Rossi, for shows directed by Luca Ronconi. He was the set designer for "Uomini e no", produced by the Piccolo Teatro di Milano, directed by Carmelo Rifici; designer and costume designer for "Avevo un bel pallone rosso", by Angela Demattè and Carmelo Rifici, production of LAC Lugano; set designer for “Macbeth, the inner things”, “Traumnovelle”, “Midsummer night's dream”, directed by Carmelo Rifici.
He drawn the sets for the documentary film "Gauguin in Tahiti. The Lost Paradise" and "Freud 2.0 - The fate of a thought that changed the world", written by Matteo Testa and directed by Claudio Poli; "Anne Frank, parallel stories" with Hellen Mirren, written and directed by Sabina Fedeli and Anna Migotto; "Modigliani, until the last breath", by Arianna Marelli and Valeria Parisi. Produced by 3D Produzioni and NEXO Digital. 
Production Designer for short film “Zita Sempri”, director Stefania Spampinato (Grey’s Anatomy, Station 19), DoP Leco Moura.
He worked as Set dresser on the set of Hollywood blvd, for the movie "Once Upon a Time in Hollywood," directed by Quentin Tarantino, with set decorator Nancy Haigh.
Project leader of Piccolo Teatro for “Interiors by David Lynch. A Thinking Room”, curated by Antonio Monda for Salone del Mobile 2024, Milano.
Art Director for “Design Walk in Budapest”, curated by Rossana Orlandi during Salone del Mobile in Triennale, Milano.
Paolo teaches stagecraft at the Academy of Fine Arts in Brescia and is also dedicated to product design, obtaining awards with projects for furnishing elements.
In 2010, for De Padova, he designed the exhibition "Effetto Castiglioni", curated by Didi Gnocchi, for the first exhibition of Achille Castiglioni's historical models.