Jenny Whiteley (born Jennifer Whiteley on January 14, 1971, in Toronto) is a Canadian folk and country singer-songwriter. She has twice won Juno awards (the Canadian equivalent of a Grammy) for her albums, Heartbreak Hill (1998), and Hopetown (2004). Her 2006 album, Dear, was nominated as Best Contemporary Album in the Canadian Folk Music Awards 2007.

Raised in a musical family (she is daughter of blues musician Chris Whiteley and niece of folk musician Ken Whiteley), Whiteley began her musical career in 1976 recording with Canadian children's musician Raffi along with her brother Dan Whiteley. She came back in the 1990s with the bluegrass band Heartbreak Hill. Just prior to that band's breakup, she released her self-titled debut album in 2001, and followed up with Hopetown in 2004. Both albums won the Juno Award for Best Roots & Traditional Album of the Year. She has released two more albums since: Dear, and Forgive or Forget, both to very good reviews, and much acclaim. Her last three records have been produced by Steve Dawson, and released through Black Hen Music. She has also collaborated with Sarah Harmer, Amy Millan, Carolyn Mark, and Riley Baugus. She currently lives in eastern Ontario

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