Massimo Colombo was born on February 16, 1961, in Milan. He earned his piano diploma at the Conservatorio di Musica Giuseppe Verdi in Milan, studying piano under Alberto Colombo and composition with Davide Anzaghi and Angelo Corradini, and took further private lessons with American pianist Sonny Taylor. His recording career runs from 1988 to the present, and Discogs documents 60 artist-relationship credits under his own name, 18 of them as leader or co-leader.

His first credited group was the Massimo Colombo Trio, with bassist Marco Micheli and drummer Francesco Sotgiu, whose album Alexander appeared on Splasc(h) Records in 1989. The same year he played keyboards alongside trumpeter Enrico Rava on Toucan, credited to Giochi Proibiti Con Enrico Rava, a session that also brought in guitarist Riccardo Bianchi and saxophonist Stefano Cantini. In 1990 he co-billed Music For An Imaginary Movie with double bassist Attilio Zanchi, the first of several records the two would make together over the next three and a half decades. Games (1992, Modern Times), released as Massimo Colombo - Tino Tracanna - Naco, paired him with saxophonist Tino Tracanna and percussionist Naco across a program split between his own compositions, Tracanna's, and a Duke Ellington tune.

Through the late 1990s and early 2000s Colombo recorded a run of albums for the Milan label Symphonia Sgr, several of them blurring his jazz and classical identities. Il Suono Elegante (1998) is a solo piano record of three opus-numbered pieces. Under the name Massimo Colombo World Ensemble he composed, arranged and produced Sole (2001) and Luna (2002), large-cast sessions built around strings, voice and hand percussion that added guitarist Bebo Ferra to the group on Luna. Virtualmente (2003) and Immagini (2004) brought in trumpeter Giovanni Falzone, the latter also adding bassist Marco Micheli, guitarist Lucio Bardi and percussionist Marco Fadda; Discogs tags Immagini across four genres (Electronic, Jazz, Classical, and Folk/World/Country), reflecting how far the World Ensemble records reached outside a straight jazz format.

Caravaggio (2005) put him in a trio with electric bassist Jeff Berlin and drummer Billy Cobham, released under the billing "Massimo Colombo Feat. Jeff Berlin - Billy Cobham" and engineered by Miroslav Vitous. Assolo In Equilibrio (2006) returned to solo piano. Everybody's Song (2008) was a five-way co-billing with singer Lara Iacovini, Attilio Zanchi, drummer Mauro Beggio and pianist Roberto Cipelli, while the same year's Il Gioco Delle Forme was a trio with British-Israeli drummer Asaf Sirkis and bassist Yuri Goloubev. Doppia Traccia (2010) was a duo record with saxophonist Felice Clemente, and Colombo appears on piano across several of Clemente's own group releases from the same period, including Blue of Mine (2009) and Nuvole Di Carta (2011), both featuring bassist Giulio Corini.

Colombo's longest-running international partnership has been with drummer Peter Erskine. Trio Grande (2015), recorded in Los Angeles with bassist Darek Oleszkiewicz, is the record he and reviewers most often point to as his fullest statement as a trio leader. We All Love Burt Bacharach (2016) expanded the group with saxophonist Bob Mintzer, trumpeter Michael Stever and vocalist Kathleen Grace; per his Conservatorio di Como teaching biography, the arrangement was submitted for Grammy Award consideration in 2017. The pair reunited in 2022, with bassist Chuck Berghofer in place of Oleszkiewicz, for Electric Parker, a set of ten Charlie Parker themes on which Colombo played Fender Rhodes rather than acoustic piano, recorded partly between his own studio in Milan and Erskine's in Los Angeles and reviewed in Italy by Musica Jazz.

Colombo's solo and small-group work since 2017 has kept pairing jazz vocabulary with classical structure. Tempered Blues (2017, UR Records), a solo piano set, sets 48 blues pieces across all 24 major and minor keys in deliberate homage to the structure of Bach's Well-Tempered Clavier; a companion score is published by Da Vinci Edition. Powell To The People (2018, Jazzland DZ) is a trio tribute to Bud Powell with bassist Maurizio Quintavalle and drummer Enzo Zirilli, a group Colombo formed after the three met teaching together at the Conservatorio Niccolo Piccinni in Bari in 2015; the same trio recorded Acoustic Weather - The Music Of Weather Report (2019). Personalities (2020) is a solo piano set of twelve tracks, each named for a person. Neither Powell To The People nor Electric Parker is catalogued under Colombo's artist entity on Discogs; both are documented here from All About Jazz and Musica Jazz reviews instead.

Alongside performing, Colombo has taught piano and harmony at Milan's Centro Professione Musica (CPM) from 1990 to 2020, jazz arrangement at the Conservatorio Giuseppe Verdi in Milan from 2006 to 2012, and jazz piano at conservatories in Pescara, Bari and Piacenza; since 2020 he has held a tenured professorship in jazz piano and jazz composition at the Conservatorio Giuseppe Verdi in Como. A 2009 concerto for jazz trio and string orchestra, Concerto Per Trio Jazz Ed Orchestra D'Archi, premiered at the Padova Jazz Festival. He is also a prolific classical composer under his own opus numbers, with works published by Carisch, Hal Leonard and Da Vinci Edition; Italian Wikipedia and his conservatory biography both describe a catalog of more than 700 compositions, a figure this profile reports as a press and institutional claim rather than an independently itemized count.

All About Jazz has called Colombo Italy's "erudite" jazz pianist, a description that fits a musician who moves between a bebop-rooted trio language, shaped by his explicit study of Bud Powell on Powell To The People, and a parallel career as a classical composer working in opus-numbered forms. Tempered Blues, which sets blues variations across all 24 keys on the model of Bach's Well-Tempered Clavier, is the clearest expression of that double grounding, and the 2009 concerto for jazz trio and string orchestra points the same way from the other direction. His working trios with Peter Erskine lean toward a mainstream, tune-based jazz vocabulary, while the Massimo Colombo World Ensemble records of the early 2000s pulled in strings, hand percussion and multiple languages of voice, closer to jazz fusion and world-jazz territory than his trio dates.