[3][4][5] He grew up in Adelaide, South Australia,[citation needed] and first played junior football with Central District in the SANFL.

[6] Selected in the third round of the 1994 National Draft, O'Loughlin played 12 senior games for the Swans in 1995 and earned an AFL Rising Star award nomination.

The following year, he was a key player in the team that won the minor premiership and then lost to North Melbourne in the grand final.

[citation needed] O'Loughlin played the majority of his early football in a half-forward flanker role, where his combination of speed, strength and agility made him a difficult player for opposing teams to match up against.

[citation needed] In 2005, he was selected alongside Sydney Swans teammate and cousin Adam Goodes in the Indigenous Team of the Century.

[citation needed] O'Loughlin, the only player remaining in the team from the 1996 loss, played strongly during the 2005 grand final, including a number of exceptional marks.

The moment is captured in Jamie Cooper's painting the Game That Made Australia, commissioned by the AFL in 2008 to celebrate the 150th anniversary of the sport.

O'Loughlin also represented South Australia against Victoria in the State of Origin Slowdown charity match at the Adelaide Oval on 3 October 2011.

[16] In 2000, it was alleged that O'Loughlin had been present during the rape of a woman in a park in Adelaide by two other AFL players, Adam Heuskes and Peter Burgoyne.

The case, however, did not go to court as the Director of Public Prosecutions, Paul Rofe, said there was "no reasonable prospect of conviction on any criminal charge" due to a lack of witnesses.