The Wailin' Jennys are a Canadian music group. They have released several albums and received a Juno Award. The group has been featured on the American Public Media program A Prairie Home Companion and their album Firecracker peaked at number two on the Billboard Bluegrass charts, in 2006.
The group was founded in 2002, when a Winnipeg guitar shop called Sled Dog Music brought Ruth Moody, Nicky Mehta and Cara Luft together for a joint performance. The show was well received and the owner scheduled a follow-up performance and suggested they "go on tour and call themselves the Wailin' Jennys." The group's name is a pun on the country singer Waylon Jennings.
The group now consists of soprano Ruth Moody, mezzo Nicky Mehta and alto Heather Masse. In previous years, the Jennys have also toured with fiddler and mandolinist Jeremy Penner, who is from Ruth's former band, Scruj MacDuhk. Other band members have included Annabelle Chvostek, a singer/songwriter from Montreal and Ruth Moody's brother Richard on viola and mandolin. Both Penner and Moody have appeared on The Wailin' Jennys' albums. In 2007, Chvostek left the group and was replaced by Heather Masse, a Maine-born singer and member of the band Heather & the Barbarians.
The Wailin' Jennys have won two Juno Awards for Roots and Traditional Album of the Year (Group) in 2005 for 40 Days and in 2012 for Bright Morning Stars. They were also nominated for the same award for Firecracker in 2007.