Woods' first album,
The Hold Up, was released in 2007. His second album,
The Widowmaker, was released in 2010, and garnered Woods' first
Juno Award nomination for Roots & Traditional Album of the Year: Solo. His fourth album, ''Hard Settle, Ain't Troubled'', was released February 26, 2016, and was a longlisted nominee for the
2016 Polaris Music Prize. At the
12th Canadian Folk Music Awards, Woods won the award for English Songwriter of the Year, and the album was nominated for Contemporary Album of the Year. Woods' fifth full-length album
Both Ways was released on April 20, 2018. At the
Juno Awards of 2019,
Both Ways won the
Juno Award for Contemporary Roots Album of the Year. In May 2019 Woods released
The Other Way, a companion album to
Both Ways which featured more acoustic-based renditions of the prior album's songs.
The Other Way included guest vocals from
Tenille Townes on "I Ain't Ever Loved No One", The album featured guest vocals from both
Katie Pruitt and
Rhys Lewis as well as songwriting credits from
Ashley Monroe,
Tucker Beathard,
Thomas Finchum and
Ed Robertson of
Barenaked Ladies. As part of the release, Woods launched the
Donovan Woods With People Project, which featured dancers and visual artists from multiple countries creating pieces inspired by songs from the album. One of the project's featured artists was Brooklyn-based singer-songwriter,
Ariana and the Rose. On May 7, 2021, Woods released the song "IOWA" with
Aoife O'Donovan. On March 18, 2022, Woods released his EP,
Big Hurt Boy. He subsequently opened for
Matt Nathanson on his "Some Mad Hope 15th Anniversary Tour" in the United States. In 2023, he participated in an all-star recording of
Serena Ryder's single "
What I Wouldn't Do", which was released as a charity single to benefit
Kids Help Phone's Feel Out Loud campaign for youth mental health. On July 12, 2024, his most recent album, "Things Were Never Good If They're Not Good Now" was released by End Times Music, an indie label founded by Woods and Michelle Szeto. The record features 11 songs and two bonus tracks. It was longlisted for the
2025 Polaris Music Prize. In January 2026, Woods announced an EP,
Squander Your Gifts, set to be released on February 27, 2026.
Songwriting Woods' song "Portland, Maine" (co-written with Abe Stoklasa) has also been recorded by
Tim McGraw. Woods' song "Leaving Nashville" (also co-written with Abe Stoklasa) has been recorded by
Lady A singer
Charles Kelley. Woods was signed to Warner/Chappell Nashville in 2016. In 2018, Woods was a
SOCAN Songwriting Prize nominee as cowriter of
James Barker Band's song "
Chills". He has also co-written the number one
Canada Country hits "
Feels Like That" by
the Reklaws and "
Forever's Gotta Start Somewhere" by
Chad Brownlee.
Film/TV Syncs Woods' song "Brand New Gun" was featured in the movie
Numb starring
Matthew Perry. His song "Wait and See" was featured on
Degrassi: The Next Generation, and his song "My Cousin Has a Grey Cup Ring" was used in commercials for the
Grey Cup. His song "Kennedy" was featured on an episode of
The Good Doctor in 2017, "Don't Get Too Grand" was featured on
Rookie Blue and "Portland, Maine" was featured on season 1 of
Legacies in 2019. Woods' has had other placements in shows like
Felicity, Less Than Kind and
The Fosters. Woods wrote "The Heart of Christmas" performed by
Alicia Witt in the Hallmark movie,
Our Christmas Love Song. ==Discography==