Related Information for Wailin' Jennys The Wailin' Jennys is a Canadian folk music trio originating in Winnipeg, Manitoba. Their name is a pun on country singer Waylon Jennings. Since forming in 2002 when a local music shop brought together three solo acts for a performance, the trio has released a series of albums, two of which have won Juno Awards, Canada's top music industry award. Their album "40 Days" won the "Roots and Traditional Album of the Year by a Group" in 2005, as did their album "Brig.. read more