Butterbean suffered his first defeat in 1995 - and it came in brutal fashion at the hands of the late Mitchell Rose.
Eric 'Butterbean' Esch shot to fame for his career in combat sports, and became an icon in boxing throughout a 16-year heavyweight career.
Esch developed a cult following during his stint in the ring, with fans fascinated by his 300lbs to 400lbs physique which saw him largely compete as a king of the four-round format.
The American star had made a fantastic start to his professional career, winning all of his first 15 professional fights, which led to a huge battle in the 'Mecca of Boxing'.
Butterbean came up against Mitchell Rose in a headline act at New York's Madison Square Garden in December 1995.
Rose had got himself in shape as a sparring partner to heavyweight legend Mike Tyson who was facing Buster Mathis Jr.
His knockout record had seen him built up as favourite as fans flocked to see him produce yet another brutal stoppage.
But it happened in anything but the way it was expected to pan out, with Butterbean on the back foot from the opening bell.
And in just the second round, Esch was left simply bewildered as his rival went on to the front foot and let his hands go.
It was a complete onslaught with Rose badly inflicting damage to his domestic counterpart who was clinging on for dear life.
And as he retreated to the corner of the ropes, the referee stepped in and halted Butterbean for the first time in his career.
It was an astonishing turn of events and fans could hardly believe what had unfolded.
Throwback to when iconic boxer Butterbean left his rival flat on his back with huge one-punch KO to overcome one of biggest weight differences in boxing history
It was just one of two victories for Rose, who retired with a record of just a couple of wins and eleven defeats.
Despite having a limited career, Butterbean's rival had an interesting back story having made a phenomenal claim he was involved in a street fight with 'Iron Mike'.
Six years after his famous night, Rose had claimed he was involved in a fiery brawl with Tyson outside a Brooklyn night club.
He then sued the legend for $66 million [£51 million] claiming Tyson had injured his back and ‘ripped his mink coat with his bare hands'.
The late boxer recalled the confrontation in his autobiography writing: "I wasn't in a boxing state of mind. He was very, very strong. I slipped backwards on the concrete.
"But I wasn't scared. I should have been, but I wasn't. I think Mike expected me to fold and surrender.
"Either way, I can say I got to fight Mike Tyson. It wasn't in the ring where I would have liked to get the payday. It was the Brooklyn way, in the street."
Rose also claimed he earned just $1500 for his sensational win over Butterbean, a small purse for the magnitude of the fight.
He went on to reveal exactly how big the defeat was for his name at the time.
Rose added: “Beating Butterbean at the Garden was my version of the Thrilla in Manila. It’s been almost ten years.
"I still get a lot of respect for that fight. That is one of the few times I had time to train, about five weeks, and I surprised many people.
"It was me everyone was usually laughing at. For a guy who was always walking around down and out, that was a triumphant moment for me.”
Despite the defeat, Butterbean went on to maintain his stardom and become one of the sport's most unlikely big names.
He retired in 2013 with a record of 77 wins, 10 defeats and four draws, competing against the likes of Larry Holmes and Peter McNeeley.
Since his days in the spotlight, Esch has made a monumental physique transformation having shed a total of 200lbs.
Butterbean initially pondered with the idea of a full comeback, calling out YouTube star Jake Paul.
But that idea now appears to be in the past, with the legend focusing on potential exploits in wrestling, with less physical risk.
Instead, his son stepped into the ring in April of this year for his pro boxing debut, but this did not go as he'd have hoped.
Eric's son Matthew Caleb Esch took to the ring in an attempt to follow in his father's famous footsteps.
The 5ft 9ins youngster made his professional debut against Joshua Brice, but did not get the win he desired.
Esch was knocked out in round two of the four-round contest after taking a brutal body shot from Brice.
He could not recover and sat out the referee's count, so is now 0-1 as a pro boxer as a result.