Matt Castellvi
Matt Castellvi is a Cuban-American comedian, improviser, and teacher from Chicago who has built a career spanning stand-up, musical improv, and sketch performance across the United States and Europe. Trained at Second City, iO, and ComedySportz in Chicago, he won Best Stand-Up of 2019 from the Chicago Reader and performed at festivals in Australia, Norway, and across North America before joining the cast of Boom Chicago in Amsterdam in 2019.
Castellvi began studying comedy in Chicago around age 18, training at The Second City, iO Theater, and ComedySportz Theater. At iO he performed regularly with The Musical Armando, the theater's long-form musical improv format, and at Second City he performed with Baby Wants Candy. He was also a member of Octavarius and a performer with the ComedySportz Chicago house ensemble. He coached in the Ensemble Improv Program at Gorilla Tango Theater.
By the late 2010s Castellvi had developed a parallel stand-up career alongside his improv work, performing four to five shows weekly in Chicago venues. The Chicago Reader named him Best Stand-Up of 2019. He headlined comedy festivals including the Adelaide Fringe Festival in Australia, the Oslo Improv Festival in Norway, the Miami Improv Festival, the Big-Little Comedy Festival, the Omaha Improv Festival, and the Chicago Musical Improv Festival.
In November 2019 Castellvi relocated to Amsterdam after he and his partner, also a musical improviser, auditioned for Boom Chicago. He joined the Boom Chicago cast as a performer and writer, and in September 2020 he premiered SITCOM, his first written review for the theater, built around 1990s sitcom themes. At Boom Chicago he also works with the academy as a teacher of improv, stand-up, character creation, and creative writing.
Alongside performance, Castellvi has offered corporate services including improv workshops, MC work, event comedy writing, and comedy roasting for organizational clients. His teaching work has spanned the United States and Europe, extending the reach of his Chicago improv training into international comedy contexts.
Historical Context
Castellvi's trajectory from Chicago training to international performance followed the pattern of several Chicago-trained improvisers who built their careers across multiple comedy disciplines before finding institutional homes abroad. His path through Second City, iO, and ComedySportz gave him fluency in long-form, short-form, musical, and ensemble improv traditions simultaneously, a range that made him adaptable across the formats that European improv venues and festivals typically present.
The move to Boom Chicago in 2019 connected Castellvi to one of Europe's most internationally recognized improv institutions, a theater that has historically recruited performers with strong Chicago or New York training backgrounds and has consistently toured and exported its work across the continent. The 2020 premiere of SITCOM, his first written review for Boom Chicago, demonstrated his expansion into the sketch-writing and scripted-review format that has defined Boom Chicago's theatrical identity since its founding in 1993.
The festival circuit Castellvi worked before his Amsterdam move, from the Adelaide Fringe to the Oslo Improv Festival, represented a strategic investment in international visibility that many Chicago improvisers pursue as a path toward European performance opportunities. His Chicago Reader recognition as Best Stand-Up while still active in the Chicago improv community also illustrated the relatively permeable boundaries between stand-up and improv in that scene.
Teaching Philosophy
Castellvi's teaching draws on training across three of Chicago's major improv and comedy institutions: The Second City, iO Theater, and ComedySportz Theater, each of which represents a distinct tradition within the Chicago comedy ecosystem. The Second City's character-based ensemble approach, iO's long-form Group Mind orientation developed through the Harold, and ComedySportz's short-form competitive format give his pedagogy a cross-institutional breadth that allows him to engage with students approaching improv from multiple performance contexts and objectives.
His experience with The Musical Armando at iO, iO's long-form musical improv format, gives his teaching a musical dimension that distinguishes it from pedagogies focused on spoken word improv alone. Musical improv demands a particular kind of ensemble listening, the ability to receive and incorporate musical offers alongside verbal and physical ones, and his deep immersion in that format at iO has shaped a teaching approach that treats musical responsiveness as an integral rather than supplementary improv skill.
At Gorilla Tango Theater, where he coached in the Ensemble Improv Program, and through his work with Baby Wants Candy at Second City, he developed his skills as both an ensemble performer and a pedagogue, learning the specific challenges of teaching long-form musical improv to performers at various levels of skill and musical experience.
His parallel career as a stand-up comedian performing on national and international stages has given his improv teaching a cross-genre perspective, allowing him to articulate the similarities and distinctions between improvisational ensemble performance and the solo comedic form. This comparative awareness enriches his coaching by giving students insight into how the same core skills of authentic presence, clear point of view, and audience responsiveness apply differently across performance contexts.
Legacy
Castellvi's career documents the internationalization of Chicago improv training, as performers who built their craft at Second City, iO, and related institutions have increasingly found sustained professional homes in European theater contexts. His work at Boom Chicago places him within that institution's ongoing effort to maintain a cast drawn from the North American improv mainstream while serving Amsterdam and touring audiences across Europe. The Musical Armando work at iO and the stand-up recognition from the Chicago Reader represent two different markers of his standing within Chicago's comedy community before his relocation. His corporate training work and teaching at Boom Chicago's academy extend the applied and educational dimensions of improv that both institutions have long treated as central to their institutional mission.
Recommended Reading
Books are ordered from the strongest direct connection outward to broader relevance.

Group Improvisation
The Manual of Ensemble Improv Games
Peter Campbell Gwinn; Charna Halpern

Improvise!
Use the Secrets of Improv to Achieve Extraordinary Results at Work
Max Dickins

Putting Improv to Work
Spontaneous Performance for Leadership, Learning, and Life
Greg Hohn

The Art of Making Sh!t Up
Using the Principles of Improv to Become an Unstoppable Powerhouse
Norm LaViolette; Bob Melley

Comedy and Distinction
The Cultural Currency of a 'Good' Sense of Humour
Sam Friedman

Process: An Improviser's Journey
Mary Scruggs; Michael J. Gellman
References
How to Reference This Page
The Improv Archive. (2026). Matt Castellvi. Retrieved March 19, 2026, from https://improvarchive.org/people/matt-castellvi
The Improv Archive. "Matt Castellvi." The Improv Archive, 2026. https://improvarchive.org/people/matt-castellvi.
The Improv Archive. "Matt Castellvi." The Improv Archive, 2026, https://improvarchive.org/people/matt-castellvi. Accessed March 19, 2026.
The Improv Archive is a systemically maintained repository. The archive itself acts as the corporate author.