[9] Self-taught to play piano and guitar, Smith also studied visual art throughout her primary, secondary and post-secondary school career, ultimately graduating from Sheridan College's animation program.

[citation needed] Smith began playing free stages while in college, and upon relocating to Canada's east coast, started to pursue music more seriously.

Two EP-length recordings - The Cricket's Quartet (2008) and Wish Upon a Star (2009) - were also released during this period, as was Smith's rendition of the Pixies song "Here Comes Your Man", which was included on the (500) Days of Summer soundtrack (2009).

These include popular standards from the first half of the 20th century, Motown, modern electronic, sample and loop-based composition, the work of eclectic pop artists like Björk and Ellie Goulding, alt-rockers the Pixies, and contemporary Canadian musicians like Sarah Mclachlan, kd lang, Jane Siberry and Leslie Feist.

[11][13][14] The sound of The Cricket's Orchestra (2009) was dubbed 'modern vintage' by Smith, an aesthetic blending early 20th century jazz, swing band, country and folk music with contemporary electronic and club textures.

[16] Have A Heart recasts the jazz, folk and baroque character of Smith's earlier work in a modern popular music context that Popdose reviewer Jeff Giles described as "designed to challenge her audience's expectations - and test her own artistic boundaries - without sacrificing her original appeal.

[18][19] In a review for The Cricket's Orchestra, New York Times music critic Jon Pareles opined that Smith's songs are "wry and retro, with wordplay harking back to Tin Pan Alley's heyday.