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O'Sullivan became world champion for the first time with an 18-14 win over John Higgins in 2001 before producing further victories in 2004, 2008, 2012 and 2013 at the Crucible Theatre in Sheffield.
After watching fellow Class of '92 colleagues Higgins claim the crown for the first time in 1998 and Mark Williams triumph in 2000, O'Sullivan admits he was feeling the pressure the longer the drought progressed.
Thoughts of emulating his mate and fellow Eurosport pundit Jimmy White – who lost finals in 1984, 1990, 1991, 1992, 1993 and 1994 – crossed his mind when he reached the age of 25 without having reached the final of the game's ultimate event.
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"There were points in my life when I thought I was never going to get to the final or win it," O'Sullivan told Eurosport.
"To get to the final was a great achievement. Playing John (Higgins) in the final was never going to be easy as he had won it once by then in 1998.
"The pressure was on me to get a victory. It was nice to win one, and the feeling of relief that went with it.
"I remember thinking: 'Bloody hell, I ain't got to answer questions any more about being the best player never to win the World Championship'.
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"I realise I had to get the monkey off my back like Phil Mickelson managed to do by winning his first Major in golf at the US Masters. I relaxed a bit, and thought that the pressure lifted on me once I got that out the way to hopefully make room for some more."
O'Sullivan will face Ding Junhui for a place in the quarter-finals over the best of 25 frames on Friday, Saturday and Sunday, but will hope for better form than his debut at the Crucible.
He lost 10-7 to Alan McManus in the first round in 1993 with a highest break of 79 and no other contributions over 50.
"I couldn't believe that I had qualified for the tournament. Alan was one of my heroes at the time," said O'Sullivan, who thumped Thepchaiya Un-Nooh 10-1 in a record 108 minutes in the first round of this year's tournament. "He had just turned professional a few years before and was doing so well.
"Stephen Hendry and Steve Davis were my favourites, but they were closely followed by Alan and James Wattana because they were new guys doing well on the circuit. For me, it was like a dream come true to be playing at the Crucible against a guy I had admired and wanted to play like.
"I was disappointed with my performance because I hardly made a break over 40 or 50 in that match."