2014–2016: Early career and Bcos U Will Never B Free At age 16, O'Connor began playing the guitar and started to produce his own music using
Apple's
Logic software. On 4 September 2015,
Bcos U Will Never B Free was self-released by O'Connor free of charge on
Bandcamp and
SoundCloud.
2017–2018: Rise to prominence and Apricot Princess Bcos U Will Never B Free caught the attention of the American rapper
Tyler, the Creator, who sent him an email describing his enjoyment of the project. This led to Tyler flying O'Connor out the following year to
Los Angeles to collaborate on his album
Flower Boy, On 25 January 2017, he released the single "Best Friend" (premiering on
Apple Music's
Beats 1 station), followed later in the year by the release of his second studio album
Apricot Princess. O'Connor's first release following the success of
Apricot Princess and
Flower Boy was on 11 October 2017 with the single "
Loving Is Easy", created in collaboration with the Dutch artist
Benny Sings. On 31 May 2018, he released a cover of "
You've Got a Friend in Me" in collaboration with
Randy Newman, the creator of the song. He was also featured in
Spotify's Rise Program.
2019–2023: Pony and Who Cares? On 14 February 2019, O'Connor released the single "New House". Later that year on 12 September, he released "
10/10"; the lead single from his third album
Pony. Released on 25 October 2019,
Pony was his first major-label album release through
RCA Records. On 30 September 2020, O'Connor released an EP with recordings from his performance at
Radio City Music Hall in
New York City during his
Pony tour titled
Live at Radio City Music Hall alongside a documentary released on
YouTube. This documentary showed the events leading up to this performance as well as the early conclusion of the
Pony tour due to the
COVID-19 pandemic. In October 2020, O'Connor confirmed that he was in the process of recording a fourth studio album titled
Who Cares?. In January 2021, he liked a Tweet seemingly confirming that it would be released at some point later that year. However, this did not materialise. On 13 January 2022, he began officially teasing the album, sending out postcards containing a phone number that when called, a snippet of a song would play. The album was released on 11 March 2022, and was his first to top the
UK Albums Chart, entering ahead of
Impera by
Ghost. In July 2022, O'Connor cancelled tour dates in Australia, New Zealand and Europe due to "unforeseen personal circumstances". He then released a stand-alone single, titled "Threat", on 10 August 2022. In late 2023, O'Connor toured in countries throughout Australia and Asia. He then performed at the 2023
Camp Flog Gnaw festival.
2024–present: The Alexander Technique On 9 July 2024, O'Connor announced his fifth studio album,
The Alexander Technique, after first teasing it one week prior on
X. On 18 July 2024, O'Connor released two songs, "Alexander" and "Guitar Song" and shared the 16-song tracklist for the album, which was released on 6 September. The following year, on Valentines Day, Rex Orange County released a collaborative project with
Daniel Caesar featuring two songs, "Rearrange My World" and "There's a Field (That's Only Yours)". The same year on September 9th 2025, he released 'Take A Drive" which was collaboratively produced with
Pharrell Williams. ==Artistry==