Nicholas Anelka
The controversial but brilliantly talented striker enjoyed two seasons at Arsenal between 1997 and 1999, before he was sold for a whopping £22.3m fee to Real Madrid. He flopped in Spain though, and was shipped out to boyhood club PSG after just one season. He was still reeling from his La Liga failure however, and Liverpool’s French boss Gerard Houllier took advantage and secured a loan deal for the forward in 2001, then aged just 22. Anelka did relatively well at Liverpool, but not enough to earn himself a permanent deal at Anfield, scoring five goals in total.