The rival news show hosts battled it out in a presidential-style debate behind two podiums in Washington in an event titled 'O'Reilly v Stewart 2012: the Rumble in the Air-Conditioned Auditorium'.
The Daily Show host Stewart opened the debate with the statement: "My friend Bill O'Reilly is completely full of s**t."
The 90-minute event saw the pair take on several political issues, with Stewart utilising a motorised platform to stand above his taller opponent.
The debate's first hour was divided into five 12-minute segments and was moderated by CNN's ED Hill, with questions about the economy, the Middle East and media bias.
"I have come here tonight to plead to the mayor of Bulls**t Mountain," Stewart joked.
O'Reilly and Stewart disagreed over government spending, with the Fox News host stating that too much money was given to "slackers" who "mooch" off the government.
"Why is it if you take advantage of a tax break as a corporation you're a smart businessman, but if you take advantage of a tax break as a person you're a moocher?" Stewart responded.
The pair later swapped their podiums for white chairs in the lightning round section of the debate, answering questions submitted online and from the studio audience, with discussions including the New York soda ban and the 'war on Christmas'.
When asked which celebrity they would choose as president, O'Reilly selected Clint Eastwood. Stewart proceeded to talk to his empty chair in relation to the Hollywood actor's infamous 'Invisible Obama' speech.
Hill later asked the 'candidates' what the most valuable thing that they had learnt from their opponent was, with Stewart saying: "I have learned that bulls**t mountain is tall, bulls**t mountain is wide, and it's deep."
O'Reilly said: "That I know I'm right."