2016–2018: The X Factor & Trouble
In 2016, Terry auditioned for the thirteenth series [en] of The X Factor. During the auditions he performed a cover of "Stand by Me" by Ben E. King, he earned four yes votes from the judges. He was placed in the "boys" category and reached the live shows, where he was mentored by Nicole Scherzinger. In the semi-final, he finished in the bottom two and faced the sing-off against Emily Middlemas. Scherzinger, Louis Walsh and Sharon Osbourne voted to send him through to the final. He won the Final on 11 December 2016, over Saara Aalto, the result made him the second winner, after James Arthur, to be in the bottom two at any given stage of the competition and go on to win the show. He released his winner's single, "When Christmas Comes Around [en]", an original song written by Ed Sheeran and Amy Wadge [en]. It was the second time that the winner released an original winner's song, the first being the second series winner Shayne Ward, who released his debut single "That's My Goal [en]". Following his win, he signed with RCA Records. In July 2017, he featured in a new version of "Súbeme la Radio [en]", with Enrique Iglesias and Sean Paul. The single peaked at number 10 on the UK Singles Chart. In October 2017, he released "Sucker for You [en]" as the lead single from his debut studio album, the song peaked at number 51 on the UK Singles Chart. Trouble [en] was released in November 2017, peaking at number 29 on the UK Albums Chart, the the lowest charting debut album from any The X Factor winner. "Try" was released as the second single from the album in February 2018. In June 2018, Terry was dropped by RCA Records.
2023–2024: Closure
In October 2023, he released the single "You Don’t Know Nothing" as the lead single from his EP Closure. "Ghost of Me" was released in February 2024 as the second single from the EP. "His Car" was released in March 2024 as the third single from the EP, the song dealt with the singer opening up about being gay. In June 2024, he released a single titled "Boujee". The EP, Closure, was released in November 2024.