Osvaldo Di Dio is one of Italy's most sought-after session men with collaborations with Eros Ramazzotti, Franco Battiato, Cristiano De André, Gianni Morandi and many others.
He has also worked in the studio with producers Chris Kimsey(The Rolling Stones, Led Zeppelin, Pink Floyd) and Craig Bauer(Ed Sheeran, Justin Timberlake, Kanye West) in London and Los Angeles.

In March 2020, the Foreign Ministry invited Osvaldo Di Dio to represent his hometown Naples within the #WeAreItaly project, whose mission is the promotion of Italian art and culture around the world, along with Paolo Conte, Uto Ughi, Nicola Piovani, Enrico Rava, and Renato Zero.

In September 2021 he performed at the 78th Venice International Film Festival in a duo with Cristiano De André. During the same period he was the guitarist for the Franco Battiato tribute concert at the Arena di Verona.

On April 9, 2022, he took part in the institutional ceremony of Procida 2022, Italian Capital of Culture. Osvaldo Di Dio performed his composition "Legni Paralleli" in the presence of Italian President Sergio Mattarella.

Osvaldo is also a composer and producer and, just in 2022, released his acoustic album Separations.

He is also an official endorser of the Maton brand of acoustic guitars, alongside other major artists on the Australian brand's roster such as Tommy Emmanuel, Josh Homme, Keith Urban, Eric Johnson, and John Butler.