The Wailin' Jennys

Three voices from Winnipeg

The Wailin' Jennys formed in Winnipeg in 2002. The owner of the guitar shop Sled Dog Music, John Sharples, brought Ruth Moody, Nicky Mehta and Cara Luft together for a joint performance, scheduled a follow-up and suggested they go on tour and call themselves the Wailin' Jennys, a pun on Waylon Jennings, who died the same month. The members were part-time musicians who did not expect it to last beyond a few shows. The Wailin' Jennys EP (2003) was followed by 40 Days (August 10, 2004), produced by David Travers-Smith at Private Ear Recording in Winnipeg, which won the 2005 Juno for roots and traditional album by a group.

Luft left after 40 Days for a solo career, and Annabelle Chvostek joined for Firecracker (June 6, 2006), which was recorded in fall 2005 and nominated for the 2007 Juno. Chvostek left in 2007 and the Maine-born alto Heather Masse took her place. Live at the Mauch Chunk Opera House was recorded in a single day, August 30, 2008, in Jim Thorpe, Pennsylvania, and released on August 11, 2009; Bright Morning Stars (February 8, 2011) was recorded in Haliburton, Ontario in fall 2009 and won a 2012 Juno. Fifteen (October 27, 2017), a covers album, marked fifteen years and includes songs by Tom Petty, Paul Simon, Dolly Parton and Warren Zevon.

Setlist.fm shows 82 setlists with shows from 2004 to 2026. The trio were frequent guests on A Prairie Home Companion, and played Newport Folk in 2011. Ruth Moody, born in Australia and raised in Winnipeg, has solo records including The Garden (2010), These Wilder Things (2013, with Mark Knopfler) and Wanderer (2024).