The iconic journeyman arguably played for more big clubs than anyone in history, turning out for Real Madrid, Paris Saint-Germain, Liverpool, Man City, Chelsea and Juventus, among others.
He was just a teenager when he arrived at Arsenal in 1997 - and left for Real Madrid in 1999 before showing his true potential.
But six years later, Anelka would cement his place in Gunners history, albeit while playing for Man City - who travel to Arsenal in a huge match this match.
The French forward inflicted Chelsea's only defeat of the 2004/05 season, just months after his former club Arsenal went unbeaten as the 'Invincibles'.
Anelka scored a penalty 11 minutes into the game to curtail, dealing Jose Mourinho with his first ever Premier League defeat.
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The strike would go on to be the only goal of the match, ending Chelsea's impressive unbeaten start under the newly appointed Mourinho, which had lasted until October.
It ended up being the only blemish on an otherwise flawless season.
Mourinho's side were renowned for their defensive solidity and relentless dominance, boasting a record of 29 wins, eight draws, and just that single loss across the 38-game campaign.
Despite the defeat, the Blues ultimately finished with three more victories and five more points than the previous season's 'Invincibles'.
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Had Anelka not scored that goal in October 2004, Chelsea may well have erased Arsenal's place in the history books immediately.
Former Arsenal defender Martin Keown admitted that his ex-teammate Anelka should go down as one of the club's best ever strikers.
Anelka, who once embarrassed Tony Adams in training, thrived as Arsenal's main man in his second season - firing in 17 top-flight goals from 35 matches to see him miss out on the Golden Boot by just one.
That 1998/99 campaign proved to be his final year at Arsenal, with Real Madrid snapping him up in a £22.3million deal.
With that money, Arsenal brought in Henry from Juventus for £11m, with £10m then being spent on building their London Colney training ground.
Keown admitted that he believed Anelka could have matched Henry's accolades, telling talkSPORT: "Definitely. Without a doubt. Whatever it was that Thierry Henry achieved.
"And they were big things, he was an incredible striker, Anelka had that gift as well - that pace.
"He just wanted to go on a different journey, he wasn't really that patient. I think his family around him wanted to fast-track his career.
"He ended up at Real Madrid [1999-2000], Chelsea [2008-2012] and Liverpool [2001-2002]. I was really surprised when Liverpool let him go [failed to turn loan from PSG into permanent stay].
"It was almost a relief to see the back of him out of the Premier League!
"Because for anyone who has played against him, he was an incredible talent, so naturally gifted.
"But I think he probably could have stayed at Arsenal, and everything that Henry did... we'll never know of course (if he would have broken his records).
"But it would have been lovely to have seen them both together, what a sight that would have been."
Born in France, Anelka rose to fame as a teenager after joining Arsenal from Paris Saint-Germain in 1997.
'Underappreciated' Arsenal star Nicolas Anelka sent Tony Adams back to changing room raging because he was so good says Martin Keown
Under Arsene Wenger, he quickly became one of the Premier League's most promising strikers, helping Arsenal win the Premier League and FA Cup double in the 1997-98 season.
His pace, clinical finishing, and composure earned him the nickname 'Le Sulk' due to his often aloof demeanour on the pitch.
On the international stage, Anelka earned 69 caps for France and was part of the squad that won Euro 2000.
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However, his relationship with the French national team soured over time.
He fell out with coach Raymond Domenech during the infamous 2010 World Cup, where he was sent home following a row.