After signing a recording contract with Sugar Music at age 16, she gained popularity in August 2019, when her single "Sciccherie" was shared by Cristiano Ronaldo on his Instagram profile.

Her entry "Voce", which earned her one of the most streams artist in Amazon Music Italy in 2021 alongside Cos Mass, Mahmood and Alessandra Amoroso as well as the single "Il mio amico" recorded with Fabri Fibra, were included in her debut album Madame, released on 19 March 2021.

[3][4] Being influenced by artists like Ludovico Einaudi, Calearo started taking piano lessons in middle school, and later continued to study music as an autodidact.

[16][17][18][19][20] In late 2019, Madame appeared on the album Persona by Italian rapper Marracash, performing as a featured artist in the track named after her pseudonym.

'D: The republic of women'), a magazine attached to the newspaper la Repubblica, in 2020 Madame was among the fifty candidates for the title of "Italian Woman of the Year".

[24] Madame made her first appearance on Italian television on 3 December 2020, when she opened the semi-final of the fourteenth season of The X Factor on Sky TV, singing her song "Baby" in a duet with contestant Blind.

[32] Two new songs, entitled "Marea" and "Tu mi hai capito", were released as singles on 4 July and 3 September 2021 respectively, and later added to the digital version of her debut album.

[39] On Klamour, Gabriele Zangarini compared her voice in "Sciccherie" to La Rappresentante di Lista, describing it as "sometimes enraged, then whispered, often theatrical".