The late 1980s to early-mid 1990s marked the golden era of heavyweight boxing. Legends like Mike Tyson, Lennox Lewis, and Evander Holyfield became cultural icons whose names endure across generations.
No matter how many times a figure like Mike Tyson loses to Jake Paul, their legacy remains untouchable. Fans will continue to view them through rose-tinted glasses, placing them in arbitrary lists of greatest heavyweight of all time or debating fantasy fights in online message boards.
But who could rank this trio of legends with more authority than someone who is arguably one of the most underrated heavyweights of their era, Riddick Bowe.

Riddick Bowe puts Mike Tyson in last place
Speaking to Boxing News, Bowe ranked Holyfield as No. 1, followed by Lewis and Tyson. Bowe praised Holyfield for his durability, while pointing out Holyfield’s and Lewis’ knockout victories over Tyson as his rationale for placing ‘Iron Mike’ in last place.
“I would have to say Holyfield’s number one,” Bowe said. “Lennox Lewis is second and then Mike Tyson.
“Well, I know Holyfield, no matter what you do to him and how you do it, he’s gonna be there. They know that too. Lennox I put him number two cause he’s the biggest of all of us and I guess he proved that he was durable… Mike isn’t as durable as those guys cause they knocked him out. But in his prime he was the man, he would knock anybody out.”
Holyfield fought the who’s who of heavyweight boxing in his era. ‘The Real Deal’ began at light heavyweight, laying the foundations for a successful heavyweight move for future fighters like Oleksandr Usyk.
As a relatively light heavyweight, Holyfield defeated Michael Dokes, James Douglas, Larry Holmes, Tyson (twice), Riddick Bowe, Ray Mercer, Michael Moorer, and John Ruiz. He also drew with Lewis in their first encounter.
Riddick Bowe’s underrated boxing career
Bowe remains one of the most underrated icons of the 90s era of heavyweight boxing. He retired in 2008 on the back of a nine-fight winning streak, including a two-fight disqualification streak over Andrew Golata. ‘Big Daddy’ was, and still is renowned for having one of the best jabs in boxing, something that is being replicated ever so slightly with Daniel Dubois in the modern era.
Bowe didn’t fight Tyson or Lewis, his feud with the latter was one of the biggest ‘what-ifs’ of 1990s boxing. However, he did have a legendary trilogy with Evander Holyfield where he won two of the three fights, one of which was delayed by a hang-glider crashing into the ring.