Matteo Brancaleoni was born in Milan on May 31, 1981, and started singing in the city's jazz clubs by the age of 16. His debut album, Just Smile (2006, Philology), is co-billed with pianist Renato Sellani and carries Discogs' Jazz genre tag with a Swing style credit. The session brought together a front rank of Italian jazz players: guitarist Franco Cerri, tenor saxophonist Gianni Basso, trumpeter Fabrizio Bosso, bassist Massimo Moriconi and drummer Stefano Bagnoli, with Sellani, Cerri and Brancaleoni himself sharing the arranging credits. The French magazine Jazz Hot singled him out among new talents, and its comparison of his phrasing to Frank Sinatra's has followed him since.

2007 was a breakthrough year: after a recommendation from vocalist Gegè Telesforo, his music reached Italian radio personality Fiorello, whose airplay on Viva Radio2 widened his audience considerably, and that October he sold out a show at Milan's Blue Note. He also performed a live duet with Canadian crooner Michael Bublé in Rome. The following year brought more institutional jazz recognition: Italy's Jazzit Award readers' poll placed him among the country's ten best jazz singers, and the Elba Jazz Festival named him its Best New Talent. In the same period he took a guest vocal spot, alongside singer Michela Lombardi and backed again by Sellani, Moriconi and Bagnoli, on the two-volume Chet Baker tribute Moonlight Becomes You: Thinking of Chet (Philology, 2008), and sang on pianist Andrea Pozza's Enter Eyes (2009), a duo billing with singer Andrea Celeste.

His second studio album, Live in Studio (2010, D'Herin Records), topped Italy's iTunes jazz chart for two weeks and stayed inside the top 200 of the country's overall digital jazz sales; that same year he also released his first holiday record, Merry Merry Christmas. In 2012 he issued a live big-band album recorded with the Gianpaolo Petrini Big Band, and Petrini has since stayed on as the drummer in Brancaleoni's touring "Italian Swing Band," alongside the studio album New Life (2012, Irma La Douce/D'Herin Records).

Christmas With You (2014) and Made In Italy (2015, both on Irma Records/D'Herin Records, both Discogs Jazz-tagged with Big Band and Smooth Jazz styles) followed, with Brancaleoni himself credited as producer and arranger on the latter alongside arrangers Nerio Poggi and Nino La Piana. Fabrizio Bosso returned as a featured guest trumpeter on three tracks of Made In Italy ("L'Italiano," "This Is My Life (La vita)" and "Senza Fine"). Running alongside this leader catalog is a substantial parallel career in Italy's commercial lounge and chillout market: recordings of his, most often a cover of Barry Manilow's "Copacabana" and of "How Am I Supposed to Live Without You," were licensed to more than 40 various-artist compilations on the Irma Records/Pyramide label group between 2005 and 2024.

Brancaleoni has also worked as a music journalist, contributing to Jazz Magazine and Millionaire as a member of the International Jazz Journalists Association and the International Federation of Journalists, and has additional credits as an actor.

Brancaleoni works as a Great American Songbook interpreter and swing-era crooner in the mold his own press compares to Frank Sinatra, a lineage reinforced by the veteran Italian jazz musicians who backed his debut. Discogs tags his own leader catalog consistently as Jazz, with styles running from straight Swing on Just Smile and Live in Studio through the Big Band, Smooth Jazz, Bossa Nova and Latin Jazz mix of Christmas With You and Made In Italy. Set against that is the scale of his parallel compilation-licensing career on Irma Records, a label built around lounge, chillout and nu-jazz compilations rather than acoustic jazz; that volume of commercial placements is real and worth naming plainly, but it sits alongside, rather than in place of, a leader discography that Discogs itself classifies as jazz throughout and a sideman circle drawn from the top rank of Italian jazz musicians.