Rebecca Hennessy is an award-winning trumpeter, vocalist, composer, and bandleader known for her distinctive blend of jazz, roots, and creative music. Her latest release, Makeshift Island Live at the Jazz Room (2025), captures the vibrant spontaneity of her live ensemble and follows her critically acclaimed vocal albums Joy Will Find Us (2023) and All the Little Things You Do (2020). All three recordings feature celebrated guitarist Kevin Breit (Sisters Euclid, Norah Jones), whose inventive playing adds rich texture to Hennessy’s genre-defying sound.

Rebecca’s songwriting and musical storytelling are deeply collaborative and often inspired by literature. In 2020, she was awarded a Toronto Arts Council grant to create new music based on the poetry of acclaimed Indigenous author Thomas King—an extension of a creative partnership that began in 2017. Her arrangement of King’s poem Dig Up the Stories for big band was performed by Christine Jensen’s Orchestra at the National Arts Centre in 2019. She is currently developing a new studio album featuring seven songs inspired by King’s poetry.

In addition to her vocal projects, Rebecca has released nine other albums as a bandleader or co-leader and has toured extensively throughout Canada, the U.S., Europe, Mexico, Panama, and Sri Lanka. She has recorded and performed with internationally recognized artists including Adele, Ron Sexsmith, Andy Kim, Owen Pallett, Feist, Broken Social Scene, and Yellowjackets.

A longtime fixture at Toronto’s Massey Hall, Rebecca served as bandleader and trumpeter for the Women’s Blues Revue from 2013 to 2022 and returned as a featured vocalist in 2024. She was the recipient of the Toronto Arts Foundation Emerging Jazz Artist Award in 2018 and was nominated for the Montreal Jazz Festival’s Grand Prix de Jazz in 2016. Since 2021, she has proudly performed as a Yamaha Artist, playing the YTR-8310Z trumpet.

Words from other people about Rebecca’s 2020 album, “All The Little Things You Do”

…have found it increasingly endearing after many listens. It is extremely enjoyable in a package that might be considered “light” if one didn’t pay attention. ★★★★ out of five

Keith Black – Winnipeg Free Press

It is a sonically-inspiring recording that is warm, clear, balanced and engaging… Hennessy’s trumpet playing is warm and expressive and Breit burns through some spirited and soulful guitar lines.

David Reed – Kingston Whig Standard (PostMedia)

Now and then, an album arrives that not only surpasses expectations but demands a wholesale reappraisal of the artist. A case in point is All The Little Things You Do, which recasts Rebecca Hennessy from jazz trumpeter to a singer-songwriter of the first rank. Having already distinguished herself with her FOG Brass Band project, the Toronto-based artist does so as arrestingly with this latest endeavour… The album makes one excited to contemplate what the future holds for this singular talent. For now, Hennessy can draw immense satisfaction from the wondrous accomplishment that is All The Little Things You Do. Clearly a major step in her development, it’s an album that can’t be recommended too highly.

Ron Schepper – Textura.org