The 64-year-old French coach may now be one of the most reknowned managers in world football and will take charge of his 1,000th game in charge of Arsenal at Chelsea on Saturday.
However, his appointment by the Highbury board as replacement for Bruce Rioch was something of a gamble at the time - with the ex-Monaco and Nagoya Grampus Eight boss famously sparking the "Arsene Who?" headline across the London Evening Standard in late September 1996.
And for a dressing room which contained the likes of Tony Adams, Ian Wright, Paul Merson, Nigel Winterburn, David Seaman, Steve Bould and Lee Dixon, it was certainly as much a leap of faith.
"At first we didn't really know who Arsene Wenger was," Parlour, an ambassador for the Budweiser Open Trials campaign, said.
"But we trusted (vice-chairman) David Dein at the time, him saying Arsene Wenger was going to push the club forward - and certainly after six weeks or so you could tell that he was a top-class manager.
"When Arsene Wenger first turned up, he took me to another level. His training methods were always great, he was on that pitch every single day, which is so important as a coach.
"He had lots and lots of brains about football and what he wanted to achieve."
Parlour was as a late substitute in Wenger's first match, a 2-0 Premier League win at Blackburn, and the Gunners would go on to finish in third place, missing out on Champions League qualification to Newcastle by goal difference.
Roll the clock forwards a season and Wenger's team were champions after they overhauled a 12-point lead of Manchester United and went on to claim the double with victory against Newcastle in the FA Cup final.
Parlour would become a mainstay at the heart of the Gunners' midfield engine and secured his own piece of Arsenal folklore with a spectacular 25-yard strike in the 2002 FA Cup final win over Chelsea, which marked another double for Wenger's all-conquering side.
The 41-year-old, who left Arsenal for Middlesbrough in 2004, is in no doubt of the impact Wenger had, both on a personal level for individual players and in transforming the fortunes of the club as a whole.
"I got player of the season (in 1998/1999) and that really stands out in my mind, because he made me technically a much better player and I learnt so much under him in that short period of time," said Parlour.
"You never know with managers how long they are going to stay around for.
"I always hoped when I was there, for eight years, that he would always be there, and after I left he has been there for another nine seasons.
"It just shows what he has done for the club, because now Arsenal have an absolutely brilliant new training ground, a new stadium and look at some of the players who have gone through the books.
"He has done wonders for the club and totally transformed it.
"I think Arsenal was on a slippery slope down and he brought us right up again."