Hayden entered his song "Take" in for
CFNY-FM's annual
New Music Search competition in 1993. Hayden played guitar on the track and enlisted two friends (Lorraine Ursomarzo and
Noah Mintz of
hHead) to sing vocals. Hayden continued to recruit vocalists until 1995 when he began to showcase his grainy baritone. "Take" has never been officially released on any of Hayden's albums. Hayden released an independent cassette,
In September, in 1994, Released on his own
Hardwood Records with distribution by
Sonic Unyon, the album was a commercial success. Outpost rereleased the album in the US the following year. Also in 1996, Hayden performed both nights of Neil Young's annual
Bridge School Concert, and contributed the title track to the soundtrack for
Steve Buscemi's film
Trees Lounge. For his second album, 1998's
The Closer I Get, Hayden worked with several big name record producers, including
Steve Fisk,
John Hanlon and
Scott Litt. He toured North America with a full band, including Josh Malinsky and Mitch Roth of
Poledo and Damon Richardson of
Change of Heart, to support that album. In 2004, Hayden released his follow up album,
Elk Lake Serenade, and toured North America with Oshawa's
Cuff the Duke acting as his back-up band. He subsequently released
In Field & Town in 2008, and
The Place Where We Lived in 2009. In 2010, he produced the debut album of singer-songwriter
Lou Canon, his sister-in-law. It was his first time producing material for another artist. and would play five shows in Europe as a warm up to his performance at
All Tomorrow's Parties Festival, curated by
the National. These were Hayden's first live performances since his two-song set at a benefit in Ontario over a year earlier. The album is largely biographical in nature, with tracks like "Almost Everything" noting how family now takes precedence over art in his life, and "Instructions", which details what he wants done with his body when he dies. In June 2013, the album was longlisted for the
2013 Polaris Music Prize. In February 2023 he released the single "Miss Fort Erie", his first new music since 2015. He followed up at the end of the month with the announcement that his new album
Are We Good will be released April 5, 2023, on Arts & Crafts; the announcement was accompanied by the release of the album's second preview track, a duet with
Feist titled "On a Beach". Actor
Steve Buscemi and musician
Matt Berninger of
The National appeared in the song's video.
Are We Good received a Juno Award nomination for
Adult Alternative Album of the Year at the
Juno Awards of 2024. ==Promotion==