He has been on tour with some of the most important Italian artists including Franco Battiato and Eros Ramazzotti.
He has worked in recording sessions 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.
Osvaldo's been voted by All About Jazz USA critic Karl Ackermann in the Guitar section of the 2011 annual poll, together with Bill Frisell.
In 2015 Better Days was released, the first solo album: the song Rosso Ducati was chosen by Ducati Motor to be included in the soundtrack of the Moto GP season.
In 2018, Osvaldo Di Dio released the blues-rooted album Tex Mex Sex in collaboration with British producer Chris Kimsey: the album debuted at #1 on blues charts in Italy.
In 2019 he released Guitar Stories, a four movements suite for classical guitar.
In March 2020 the Foreign Ministry invites Osvaldo Di Dio to represent his hometown Naples in the #WeAreItaly project, whose mission is the promotion of Italian art and culture in the world.
In September 2021 he performs at the 78th Venice International Film Festival.
In March 2022 he releases Separazioni: the new album highlights Osvaldo Di Dio's maturity as a composer, as well as a guitarist. The common denominator of the songs is the acoustic guitar which is now combined with a string quartet, now with a solo violin or cello, blending with minimalist and contemporary electronic elements.
He's been the only musician invited to perform in the institutional ceremony of Procida 2022, the Italian Capital of Culture. Osvaldo Di Dio played his composition Legni Paralleli in the presence of the President of the Italian Republic Sergio Mattarella, the Minister of Culture and the President of the Chamber of Deputies. The ceremony was broadcast live on the national TV channel Rai Due.