In 2004, Shepherd moved to Toronto and worked as a waitress at a piano bar. She began performing, and became a regular entertainer at the restaurant. She formed The Elizabeth Shepherd Trio with Scott Kemp on bass and Colin Kingsmore on drums. In 2006, she recorded her debut album,
Start to Move, which was voted among the top three jazz albums of 2006 by the listeners of
The Gilles Peterson Show on
BBC Radio 1. The album was nominated for a
Juno Award in 2007.
Heavy Falls the Night (2010) featured only one cover song, a reworking of "
Danny's Song". Shepherd produced the album with the exception of the first single, "Seven Bucks", which was co-produced with Japanese DJ Mitsu the Beats and climbed to No. 37 on the "
Tokio Hot 100" chart. The album was long listed for the 2010
Polaris Music Prize. In 2012, the choice of songs for her album
Rewind was influenced by her pregnancy. The album consisted of jazz-pop cover versions of
traditional pop songs by
Cole Porter, the
Gershwin brothers,
Kurt Weill, and
José Luis Perales.
Rewind was dedicated to her daughter and was nominated for the Juno Award for Vocal Jazz Album of the Year in 2012. Shepherd's album
The Signal (2014) consisted of ten original songs on topics as varied as motherhood,
Monsanto, witchcraft, and war, and featured guests such as Benin-born guitarist and composer
Lionel Loueke and drummer Larnell Lewis. The album was long-listed for the
Polaris Music Prize in 2015 and was nominated for the
Juno Award for Vocal Jazz Album of the Year in 2015. Her 2019 concept album,
MONTREAL, is a soulful blend of film and music into an ode celebrating her hometown and its rich history of untold stories. It was nominated for a JUNO Award in 2020 in the vocal jazz category. She wrote a book that accompanies the album that won 2 Word Guild Awards.
Three Things (2023) is a hybrid of soulful sounds and synth-based electronica. Created during lockdown, it features collaborations with Danish bassist Jasper Hoiby and Canadian guitarist Michael Occhipinti. Shepherd has performed at jazz clubs internationally, spanning Japan, China, Europe, North America and Central America, from Tokyo's
Cotton Club to London's
Jazz Café and Detroit's
Cliff Bell's. She has appeared at festivals on both sides of the Atlantic, including
Montreal Jazz Festival, ELB Jazz and the
North Sea Jazz Festival. In 2009, she was invited by British singer
Jamie Cullum to open for him at a sold-out show at the
Hollywood Bowl, alongside Christian McBride. She has also shared the stage with the likes of Bonobo, Five Corners Quintet, Victor Wooten, Spankie Wilson, the JazzCotech Dancers, and the Quantic Soul Orchestra. Shepherd has appeared on public radio networks around the world including
NPR (US),
P2 (Sweden),
IMER (Mexico),
ARD (Germany). She has also performed on
The Gilles Peterson Show on BBC Radio 1 (UK),
J-Wave's Modaista (Japan), and Q on
CBC Radio (Canada). She has appeared as a guest vocalist / pianist on albums by various artists, such as MC Abdominal, Peter Appleyard, Michael Occhipinti, Andrea Superstein, Drumhand, and Circle Research. Beyond her work as a musician, she has also produced albums for Andrea Superstein, Paloma Sky, as well as 5 of her own albums. ==Critical reception==