Born in Siena, Bastianini first began performing at fifteen while apprenticed to a pastry chef, Gaetano Vanni, who discovered his vocal talent and encouraged him to join the choir of his hometown's cathedral. Between 1937 and 1938, he sang bass during Masses and religious functions at the church. In 1939 he began singing lessons under Fathima and Anselmo Ammanati, who continued training him as a bass. He sang his first professional concerts in 1940 and 1941 in Asciano and Siena at the Fortezza Medicea and Teatro dei Rozzi. In 1942 he won first prize in the 6th National Singing Contest at the Teatro Comunale, Florence, but was soon drafted into the Italian Air Force which prevented him from immediately enjoying the scholarship accompanying the prize.
After serving in the Italian Air Force between 1943 and 1944 toward the end of World War II, Bastianini resumed his career. On 28 January 1945, in a Siena concert, he sang the bass arias "Vecchia zimarra" from Puccini's La bohème and "La calunnia è un venticello" from Rossini's Il barbiere di Siviglia. That November, he made his operatic debut as Colline in La bohème at the Teatro Alighieri in Ravenna. His only son, Jago, was born in 1945.
In 1946, Bastianini was finally able to enjoy the scholarship he'd won four years earlier and began studying at the Teatro Comunale, Florence. He sang in recitals there alongside other future opera greats like Mirto Picchi, Fedora Barbieri and Rolando Panerai. That same year, he appeared in numerous operas with smaller Italian opera houses such as the Teatro Verdi in Florence. Among his roles that year were his first performances of Zio Bonzo in Madama Butterfly, Don Basilio in Il barbiere di Siviglia and Sparafucile in Rigoletto.

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