At the age of six, wanting to become a singer, Stefano Bollani would accompany himself on the family keyboard. A few years later, he recorded a cassette of himself singing and playing, which he sent to his idol Renato Carosone, along with a letter explaining his dream. Carosone replied advising him to listen to a lot of blues and jazz, and so Bollani did.
His first record was the second volume of the jazz encyclopaedia published by Fratelli Fabbri. At age 11, he enrolled at the Luigi Cherubini Conservatory of Florence, where he received his diploma in piano in 1993.
At age 15, he tread the boards professionally, playing mostly pop, at the same time studying under Luca Flores, Mauro Grossi, and Franco D'Andrea whose seminars he attended at Siena Jazz.
In 1996, he met Enrico Rava at the Teatro Metastasio in Prato who immediately invited him to play in Paris with him: You're young, you don't have a family. Take the risk, give up pop and devote yourself full-time to the music you love. Taking Rava's advice, Bollani backed out of Jovanotti's tournée and flung himself into jazz, language of improvisation and freedom. His upswing was marked by rapid laps: from the important, and continuing collaboration with mentor Enrico Rava to his affirmation with a referendum held by Musica Jazz magazine (best new talent 1998); from directing his Orchestra del Titanic (with numerous concerts to its credit and two recordings for the Via Veneto label) to making records and performing tribute-shows to pop music of the past (Abbassa la tua radio with, among others, Peppe Servillo, Irene Grandi, Marco Parente, Elio from the Storie tese - and Guarda che luna! with Gianmaria Testa and Banda Osiris), right up to winning the Premio Carosone, usually awarded to singers, in September 2003 in Naples.