O'Keefe worked as an intellectual property lawyer with law firm Allens Arthur Robinson.

[5] On 31 May 2013, O'Keefe commenced playing the role of King Herod in the Australian tour of the Jesus Christ Superstar arena show.

[6][7] However, on 14 June 2013, he was admitted to hospital with a neck injury requiring surgery and was forced to relinquish the role for the rest of the tour.

[9][10][11] O'Keefe's contract with the Seven Network expired at the end of 2020, and he was replaced by Larry Emdur for The Chase Australia.

[21][22] As a result of his work with the White Ribbon Australia, O'Keefe was appointed to the inaugural National Council for the Prevention of Violence Against Women in May 2008, which drafted the report Time for Action: Australia's National Plan for Reducing Violence Against Women and their Children on behalf of the federal government.

[26][27][28] In June 2021, O'Keefe had the charges dismissed as the community magistrate found that he was in a hypomanic bipolar state when the offending occurred during altercation.

[32][33] Footage was later released during his court session in November 2023 showing O'Keefe hurling abuse at police.

[35] On 27 January 2022, O'Keefe was arrested after he allegedly grabbed a woman by the throat, pushed her to the ground, and punched and kicked her at his sister's unit in Sydney.

[41] On 23 May, O'Keefe appeared in the Supreme Court of New South Wales and was granted bail, with strict conditions that he be sent to a drug and alcohol rehabilitation facility in Swan Bay, north of Sydney, for up to a year.

Justice Hulme said O'Keefe had long struggled with mental health issues and that rehabilitation was a "good opportunity" for him.

He was scheduled to appear before the Downing Centre Local Court in June 2022 for sentencing after earlier pleading guilty to one charge of possessing 1.6 grams of cannabis.