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 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. denotes a performance that entered the ARIA Singles denotes third place
Performances on ''The X Factor''
2013: ''Jai Waetford'' EP and ''Get to Know You''
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 EP, Shy consisted of six covers and one single.
2016–2017: "Living Not Dreaming" and ''Heart Miles''
He released the single "Living Not Dreaming" in February 2016. followed by the EP Heart Miles which was released 3 June 2016. Music videos have been recorded for both 'Living Not Dreaming' and 'Heart Miles' as well as a promotional video called Heart Miles EP which shows Jai discussing a long-distance relationship featuring snippets of each of the new songs from his EP. Jai toured a variety of cities to promote his new work across Europe, Indonesia and Thailand in May and June 2016, during which he performed his new material as well as covers of Drake's single "One Dance" and Justin Bieber's "Love Yourself".
2018: Return to music, "Lost in You", "Get Over" and "Friends"
In October 2018, Waetford released his first single in a year, titled "Lost in You". Waetford said: "I wrote 'Lost in You' about someone who I met in a dark time that captivated me to a point where my life suddenly revolved around this person. When I was writing this, it was strange to me because I found myself involving her in everything I did; I was living for someone else." Waetford spoke candidly about his past mental health struggles, in an interview with the Herald Sun, saying he "couldn't find happiness in anything". After sharing his mental health struggles in a , Waetford was approached by the Australian Suicide Prevention Foundation to become an ambassador for their You Are Not Alone campaign. Waetford then released the singles "Get Over" and "Friends", which premiered with urban music outlet Complex. "Friends" is co-written by Waetford with James Agnus who also produced the record. "James and I were trying to find a sound that mashed urban drums with pop instrumentation and vocal melody," explains Jai of the collaboration. "We then stumbled across this beat James had made a while back, ran with it, and ended up really digging the result." "'Friends' is all about the online world and the real world colliding. Often we say things online that we wouldn't say in real life, and 'Friends' is about a situation where that happened to me."
