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Jai Waetford was born in 1999 and is from Campbelltown, New South Wales. He was raised by his mother Alana Dow and grandparents Hannah and Roger Dow. At a young age, Waetford's father left him and his mother. He taught himself how to play guitar from watching videos on YouTube. Waetford was a student at Campbelltown Performing Arts High School. He quit school in 2014 after completing Year 10.
In 2013, Waetford auditioned for the fifth season of The X Factor Australia, singing "Different Worlds" by Jes Hudak and an original song titled "Don't Let Me Go". He progressed to the super bootcamp stage of the competition. On the first day of super bootcamp, Waetford performed "Titanium" by David Guetta and advanced to the second stage of super bootcamp, where he sang "Last Request" by Paulo Nutini. On the final day of super bootcamp, Waetford performed "We Are Never Ever Getting Back Together" by Taylor Swift to the judges and a live audience of one thousand. He made it through to the home visits round and was put into the Under 24 Boys category, which was mentored by Ronan Keating. At the home visits, he sang Elvis Presley's version of "Always on My Mind" and made it through to the live shows. Waetford went on to reach the grand final, finishing third behind Taylor Henderson who came second and Dami Im who won the show.
After The X Factor ended Waetford signed a recording contract with Sony Music Australia. His debut single "Your Eyes", which would have been his winner's single if he had won The X Factor, was released that same day. The song peaked at number six on the ARIA Singles Chart and was certified gold by the Australian Recording Industry Association for sales exceeding 35,000 copies. On 23 November 2013, Waetford toured alongside Third Degree, Taylor Henderson, Dami Im and Jiordan Tolli for The X Factor Live Tour, which ended on 2 December 2013. On 6 December 2013, he released his self-titled debut EP, which peaked at number 21 on the ARIA Albums Chart. Waetford's second EP, Get to Know You, was released on 28 March 2014. Its title track was released as a single and peaked at number 32 on the ARIA Singles Chart. Waetford served as the supporting act for Justice Crew's #HypeTour in April 2014 around Australia. Waetford's third and most recent EP, Shy consisted of 4 covers and one single.
"The Way You Make Me Feel": Ryan, Gavin (14 September 2013). "ARIA Singles: Redfoo Is Number One". Noise11. Noise Network. Retrieved 14 September 2013.
Waetford performing at The X Factor Live Tour in November 2013