Mike Tyson is one of the most well-regarded and infamous heavyweights to have ever laced up, and was involved in some of the most memorable fights of the last fifty years.

He captured his first heavyweight world title at the age of 20 – a record that still stands to this day – and continues his rise in the sport by defeating the likes of Larry Holmes, Michael Spinks and Frank Bruno not long after.

Speaking on Complex, Tyson named not one of the above, but his first professional loss to James ‘Buster’ Douglas as his greatest fight.

“Listen, it’s weird – it has to be my loss to Buster Douglas. I say that because that fight propelled me into being a better fighter. So I always look at that fight as my best. Absolutely. Getting humiliated in front of millions and millions of people and overcoming that, that’s a winner.”

The 1990 fight saw Tyson such a heavy favourite that many bookmakers in Las Vegas refused to give a price on Douglas. What was more impressive for the Ohio native was that it wasn’t a knockout of nowhere, a punch from the gods.

He was up from the off, hitting ‘Iron’ Mike and dodging what was coming back. His jabs shut the eye of the undisputed champ, and it was almost completely closed when he scored a knockdown on Douglas in the eighth.

‘Buster’ would gain back momentum in the next round before knocking Tyson down for the first time in the tenth. The referee counted him out, and Douglas left the ring as three-belt heavyweight champion, ending Tyson’s three-year reign.

Tyson would go on a four fight win streak before being sentence to jail, missing out on what many believe would have been the prime of his fighting career. He recaptured the WBC heavyweight title in a rematch with Bruno in 1996.

Today, the man known as ‘The Baddest Man on the Planet’ is hoping to play his part in another heavyweight upset. He will be training Francis Ngannou for his fight with current champion, Tyson Fury.