Scolari graduated in architecture in Milan in 1969. In 1973 he became a professor of History of Architecture at Palermo, and of Drawing at the Istituto Universitario di Architettura di Venezia (IUAV). Between 1975 and 1993, he was visiting professor at various universities including: Cornell University, Cooper Union in New York City, the Institute for Architecture and Urban Studies in New York, Technische Universität in Vienna, Harvard University, and University of Cambridge. From 2006, he was a Davenport Visiting Professor at the Yale School of Architecture. 
From 1989, he designed furniture for Italian design company Giorgetti, where he was also the art director until 2001. 
Scolari is known for his drawings which, according to a review of his 1980 exhibition in New York, takes the form of a critique of architecture which calls to mind the surrealism of Salvador Dalí and Yves Tanguy. Pyramids and ziggurats, dams and forts, axonometric forms are used to create a new architectural "illogic".
He has held exhibitions in Europe, Japan, Russia and the United States. His works are in the permanent collections at the MoMA (New York), the German Architecture Museum (Frankfurt), and the Centre Pompidou (Paris).
Scolari's drawings were featured in the book Postmodern Visions: Drawings, Paintings, and Models by Contemporary Architects (1985). He has published his own books of (or about) his work, including Hypnos (1986). Massimo Scolari: The Representation of Architecture, 1967–2012 (2012) is the catalogue of a retrospective exhibit held at the Yale School of Architecture, curated by Scolari himself. Oblique Drawing: A History of Anti-Perspective (2012) includes a series of essays and writing about his alternative approach to perception and representation.  Pensar y representar (2013) provides an intellectual history of axonometric drawing and 'anti perspectives', central to Scolari's art. 
- "Biography '43 - 60s". Massimoscolari.it. Retrieved 2022-10-31.
- "Biography". Massimoscolari.it. Retrieved 2022-10-31.
- Hal Foster (September 1980). "Reviews: New York - Massimo Scolari, The Institute for Architecture and Urban Studies". Artforum. pp. 63–64. Retrieved 2022-10-31.
- "Massimo Scolari - Italian, born 1943". The Museum of Modern Art. Retrieved 2022-10-31.
- "Scolari Massimo Suchausgabe" [Scolari Massimo search results] (PDF) (in German). German Architecture Museum. 2020. Retrieved 2022-10-31.
- "Massimo Scolari, Architecte". Artist/personality (in French). Centre Pompidou. Retrieved 2022-10-31.
- "Postmodern Visions: Drawings, Paintings, and Models by Contemporary Architects". Publishers Weekly. Retrieved 2022-10-31.
- "Hypnos". Publishers Weekly. Retrieved 2022-10-31.
- Furuto, Alison (January 24, 2012). "Massimo Scolari: The Representation of Architecture, 1967–2012 Exhibition". ArchDaily.
- "Oblique Drawing: A History of Anti-Perspective". Publishers Weekly. Retrieved 2022-10-31.
- Eduardo Prieto (June 30, 2013). "Pensar y representar - Axonometrics, Symbolic Forms". Arquitectura Viva. Retrieved 2022-10-31.
- "Massimo Scolari wins the Arnold W. Brunner Memorial Prize". Gizmo. 2 April 2014. Retrieved 2022-10-31.
- Krier, Leon (December 2016). "Massimo Scolari". In Steil, Lucien (ed.). The Architectural Capriccio: Memory, Fantasy and Invention. Routledge. doi:10.4324/9781315241326. ISBN 9781315241326.
- Szacka, Léa-Catherine (2019). "Massimo Scolari's Ali and the institutional reframing of the Venice Biennale". In Davidts, Wouter; Holden, Susan; Paine, Ashley (eds.). Trading Between Architecture and Art. Netherlands: Valiz. pp. 121–132. ISBN 9789492095671.