Osvaldo Di Dio is one of the most sought-after session musicians in Italy, 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 Ministry of Foreign Affairs invited Osvaldo Di Dio to represent his hometown Naples within the #WeAreItaly project, whose mission is the promotion of Italian art and culture worldwide, alongside Paolo Conte, Uto Ughi, Nicola Piovani, Enrico Rava, 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 tribute concert to Franco Battiato at the Arena di Verona.

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

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

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