Reucassel was born in South Africa and later moved to Adelaide with his parents. There, he attended Semaphore Park Primary School. Reucassel later attended Bowral Public School in the Southern Highlands of New South Wales, becoming the only Chaser member to be public school educated. In 1993 while attending the school he represented the school in The Sydney Morning Herald Plain English Speaking competition, as did future Chaser member Julian Morrow.
Reucassel attended the University of Sydney, and completed a Bachelor of Economics (Social Science) degree in 1999 and graduated with a Bachelor of Laws degree in 2002. With a strong dedication to extracurricular activities on campus, Reucassel ran the Arts revue, the canoe club, and debated at several World Universities Debating Championships including ranking 30th in the World at Manila in 1999, and ranking 167th in Glasgow in 2001. Furthermore, in 2000 he competed in the Philip C. Jessup Cup international law mooting competition, his team winning the Australian rounds. He graduated from the Sydney Law School, along with Chaser colleagues Julian Morrow, Dominic Knight and Chas Licciardello.
In 2004 and 2005, Reucassel co-hosted the drive-time radio show Today Today on Triple J with fellow Chaser Chris Taylor. The pair returned with their Sunday afternoon show Bloody Sunday to do relief shifts in mid-2006 and summer 2006–07.
Reucassel was a founding member of the satirical multi-media group The Chaser team, and worked to produce their satirical newspaper, as well as television shows on ABC TV including The Election Chaser, CNNNN, The Chaser Decides and The Chaser's War on Everything. He has been one of the main presenters on The War since the pilot episode. He and his wife Keisha have three children together, and their son Ollie has appeared on some of the sketches on The War. Reucassel was often the one selected to confront former Prime Minister John Howard on his morning walks, most famously in the axe stunt (see below).
On 19 March 2007, during a campaign appearance for the New South Wales State Election, the then opposition leader Peter Debnam was confronted by Reucassel wearing nothing but Speedos and a baseball cap, making fun of Debnam's campaign appearances in the swimwear. When TV cameras remained focused on Reucassel rather than Mr Debnam, he said, "Sorry, I'm not Peter Debnam, he's over there. Just because I'm wearing this doesn't mean I'm Peter Debnam". Reucassel stuck around for the press conference but failed to draw a response from the opposition leader, and was again ignored when he went to shake Debnam's hand.
On 2 August 2006, Reucassel responded to a news story about a private school student who had hugged then Prime Minister John Howard while holding a screwdriver during one of the PM's morning walks. To test the Prime Minister's security arrangements, he approached Howard during a morning walk and asked for a hug while holding a large plastic battle axe. Reucassel did receive the hug, but a later approach while holding a running chainsaw was not so successful. There was much debate surrounding whether to turn on the chainsaw and whether they would be shot at for doing this. Cut out from this segment was an unsuccessful attempt that took place between the axe and the chainsaw, in which Reucassel was holding a four-point-star mace.
Reucassel is a Patron of the Left Right Think-Tank, Australia's first independent and non-partisan youth think-tank.The Panel – (3 episodes) (2003, 04, 07)
Spy Shop – (1 episode) (2007)
Good News Week – (3 episode) (2008–10)
Q&A – (3 episodes) (2008–11)
Top Gear Australia – (1 episode) (2010)
Balls of Steel Australia – (20 episodes – Host) (2011–2012)
You Have Been Watching – (1 episode) (2011)
The Joy of Sets – (1 episode) (2011)
The Silic & Lee Show at the Logies: Red Carpet Special 2012 – (1 episode) (2012)
The War on Waste - Series (2017).