Rae Billing, lead singer and songwriter of Crybaby, has a voice described as "honest and pure, assured and desperate at the same time." And her lyrics and music have been lauded - "full of wide open spaces and bittersweet emotions," and called "late night, pan-Americana rootsy songs... handled with gutsy femininity."

In 1996, the Toronto alt-country outfit released its debut recording, Paintings. The band lasted just four years, but won critical acclaim with Toronto's Eye Magazineplacing the album alongside offerings from Lyle Lovett and Blackie & The Rodeo Kings as one of the Top Three Country Albums of 1996, with scribe Greg Boyd praising "the weary sensuality" of Rae's vocals. The band also elicited kudos south of the border, specifically at Austin's South By Southwest Music Festival in 1997. Among the many positive reviews, visiting Nashville Scene writer Michael McCall characterized their music as "tangy country soul" and called Crybaby one of the "notable moments" at the festival.

After Crybaby, Rae went on to record three albums under her own name with a number of noted Canadian musicians. Her 2001 self-titled album was praised. Her 2008 recording, Blue Black Night, again received critical acclaim, with CBC Radio's Jeff Goodes choosing it as his top Pick of the Month. And 2013's Walls and Fences was chosen as the monthly Number One Album by Canada's respected national roots magazine Penguin Eggs, describing it as "captivating from start to finish".

Late in 2016, Rae brought Crybaby back together to play two 20-year anniversary shows. Alongside Rae, the reunited band includes Steve Koch (Ron Sexsmith) on guitar and Lucky Pete Lambert (Kensington Hillbillies) on drums and backups with the addition of respected Hamilton musicians, Andrew Aldridge (Sarah Slean) on guitar, Greg Brisco (Ginger St. James) on keys and Scott Bell (Dinner Belles) on bass.

The new Crybaby album, entitled Still, was released in April 2018.

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