Jason Reilly was born in Toronto, Canada, where he was trained at the National Ballet School in Toronto. During the student period he has already danced in ballets such as The Nutcracker and Pastorale (both: James Kudelka), choreographers such as Glen Gilmour (in Boys Dance), John Neumeier (in Yondering) and David Nixon (in Sudden Impulse) have created roles on of him.
After his graduation in 1997 he joined the Stuttgart Ballet. In 2000/2001 he was promoted to Demi Soloist, one season later at Soloist.
From the 2003/04 season he danced as the first dancer.
With the Stuttgart Ballet Jason Reilly danced numerous important roles in full-length ballets by famous choreographers.
Jason Reilly joined the Stuttgart Ballet on tours and guest performances all over the world. When the Stuttgart Ballet toured the United States in 2003, it won international recognition for the role of the male lead in John Cranko's Romeo and Juliet. He also danced with internationally renowned dancers such as Alessandra Ferri, Evelyn Hart and Greta Hodgkinson. In the new production of A Tram called Desire (John Neumeier) in 2004 he danced the role of Stanley Kowalsky together with Alessandra Ferri. When Canadian star dancer Evelyn Hart retired from her thirty-year career and wished to dance to Juliet for the last time in April 2004, she asked Jason Reilly to be her Romeo. He also chose him as his dance partner when he took to the stage in 2006. In October of the same year, Jason Reilly held several guest performances by Glen Tetleys Voluntaries with the Royal Ballet of London. In 2007, he danced the role of Petrucchio in John Cranko's The Taming of the Shrew with the National Ballet of Canada played by Greta Hodgkinson as Kate.
Because of his exceptional interpretation of classical roles combined with his expression and technical brilliance in modern ballets, Jason Reilly was nominated in the "Outstanding Dancer" category in the selection of the ballettanz magazine's annual critics several times. In February 2006 Jason Reilly received the German "German Dance Award", which is awarded annually by the German Dance Education Association and the German Association for the Promotion of Dance Art.
In September 2015 he was awarded the national title of "Kammertänzer".