Childhood and early years Jane Stewart was born in
Toronto in 1955 and was raised in the suburb of
Etobicoke. She would take her subsequent surname, "Siberry", from the family name of her maternal aunt and uncle. Many years later, she would explain this choice by stating "this woman and her husband were the first couple I met where I could feel the love between them and I held that in front of me as a reference point." and developing her own concepts of notation and structure. At school she learned conventional
music theory (as well as French horn) and taught herself to play guitar by working through
Leonard Cohen songs. Her first song was completed at the age of seventeen, although she had been developing song ideas since much earlier. Following high-school graduation from Richview Collegiate in Etobicoke, Ontario, and then the Canadian Junior College, Lausanne, Switzerland, Siberry moved on to study music at the
University of Guelph, later switching to
microbiology (in which she gained a BSc degree) as well as giving her first opportunity to play live in New York. In 1990, she embarked on a 50-date tour of Japan, Australia, New Zealand, Britain, the United States and Canada. In contrast to its predecessor,
When I Was a Boy was influenced by funk, dance and gospel music and featured extensive use of layering and sampler technology, and launched three singles – "Calling All Angels", "
Sail Across the Water" and "Temple". Prior to the release of
When I Was a Boy, Siberry performed in
Edinburgh as the opening act for
Mike Oldfield's premiere of
Tubular Bells 2. She met with a disastrous rejection by the audience. Initially, Siberry was devastated (later describing herself as having "cried for two weeks") and had to make a serious reassessment of her perspective on her work. From this point onwards, she chose to reclaim her art for herself and decided "I took back all the power back that I had put outside myself trying to please (others). The worst show of my life has become the best show because it's given me the ultimate freedom to care only about what I think is really good. How my career does is secondary." before being released in 1994 as the album
Count Your Blessings. During 1994 Siberry recorded sporadically, without constructing a new album. She came to the attention of a new audience when her song "It Can't Rain All the Time" was included on the
soundtrack for the movie
The Crow; time spent with Peter Gabriel at
Real World Studios resulted in three more songs (not released for another seven years) and she sang on the
Indigo Girls album
Swamp Ophelia.
Sheeba Records period New York period (1996–1997) In 1996, Siberry founded her own Toronto-based independent label,
Sheeba Records, on which she has released all of her subsequent material. In 1996, she performed four concerts at the city's famous
Bottom Line jazz club – all of which were recorded and released on a set of live albums between 1997 and 1999, collectively known as the "New York City Trilogy". Siberry took two years to restore Sheeba's precarious fortunes,
"Issa" period (2006–2009) Early in 2006, Siberry closed her Sheeba office, then auctioned and sold nearly all of her possessions via
eBay – including her Toronto home and her musical instruments. She retained one travelling guitar, but none of the other instruments featured on her albums and in her concerts. In 2006, she told
The Globe and Mail that she had kept a very few precious possessions, including her
Miles Davis CDs, in storage. On 3 June 2006, somewhere in northwestern Europe, Siberry changed her name to
Issa: revealing this change of identity to the public a couple of weeks later on 24 June 2006. She told
The Globe and Mail that she chose the name Issa as a feminine variant of
Isaiah. in which she offered to play small venues – ranging from intimate cafés to fans' own homes – in any location in Europe where one or more fans could organize a space, an audience of about 20 to 30 people and a night of accommodation. She had previously employed a flexible pricing policy, stating "I started feeling weird about holding back anything people wanted because of the money. It just felt wrong to my stomach, so I made a flexible interface so people could take it with whatever reasoning they felt was right, and I didn't have to worry about it any more." Siberry is featured in the
Corey Hart single "10,000 Horses", which was released on 8 April 2014. Her 1985 album
The Speckless Sky won the jury vote for the
Polaris Heritage Prize at the
2025 Polaris Music Prize. In her acceptance speech she announced the forthcoming release of
In the Thicket of Our Own Unconsciousness, her first new album since 2016. In the same year, she was inducted into the
Canadian Songwriters Hall of Fame. ==Musical style and commercial approach==