The Craziest Ring Entrances In Boxing History

Boxing is one of the most popular spectator sports in the world. Its fast-paced, adrenaline-laced showcases of warrior heart and explosive firepower in the ring has captivated fans from all over the world.

We all love a good show, and showmanship is a huge part of boxing. A boxing event’s marketability is affected by factors that extend beyond the ropes. Which is why some charismatic athletes are better remembered for their flair outside the ring, rather than the time they spent in it.

The better an athlete can play to the crowd, the more fans care. This highlights the importance of putting on a good show, and is probably why some athletes go the extra mile to captivate their audiences.

One of the most exciting parts of a boxing match is the ring entrance, when a fighter makes that walk down the ramp, entourage following steadily behind him, as he psyches himself up for war. The image on the monitor blaring as fighters get ready to go to battle, it’s enough to send chills down every fan’s spine.

While some fighters choose to keep it simple, others have a passion for riling up the crowd. Throughout history, there are many crazy ring entrances that have been burned into our memory. Let’s take a look at a handful of them.

Today, Evolve Daily shares five of the craziest ring entrances in boxing history.


1) Floyd “Money” Mayweather’s Cinco De Mayo Ensemble and Mini-Concert

Floyd Mayweather Jr. and Oscar De La Hoya squared off against each other on the 5th of May in 2007. Mayweather was just beginning to establish himself as a bonafide box office draw, while De La Hoya was the sport’s brightest star. A Mexican-American with millions of fans around the world, Mayweather and De La Hoya met at the center of the ring on the most significant Mexican boxing holiday of Cinco de Mayo.

On his way down the ramp, Mayweather showed off his gaudy Mexican flag-themed ensemble, topped off with a classy white sombrero.

If that wasn’t extra enough for you, his spectacularly provocative display was accompanied by a short performance from rap superstar 50 Cent, who hyped up the crowd with clever wordplay as Mayweather made his way to the ring.

Saying that his antics were incredibly disliked by a partisan Mexican crowd would be nothing short of an understatement.

But while Mayweather put on that performance to aggravate De La Hoya in part, it wasn’t the only reason. In an email to ESPN, he said, “It was to honor my uncle Roger.” The late Roger “The Mexican Assassin” Mayweather famously wore a black sombrero before he retired from the ring.


2) Bernard Hopkins’s Special Boxing Rendition of Frank Sinatra’s “My Way”

Known throughout the majority of his career as “The Executioner”, Bernard Hopkins had a knack for showmanship. If this list were about the most intimidating ring entrances, this one would definitely be a candidate for the top spot.

Hopkins was always a terrifying image, sure to make any child cry. Dressed in black with his signature hood up and an executioner’s mask obscuring his face, Hopkins looked like an omen for his opponent’s demise.

Against equal legend Roy Jones Jr. in April 2010, Hopkins took the horror up a notch, penning his own rendition of Frank Sinatra’s My Way. The lyrics to the song eerily depicted how Hopkins wanted to beat Jones. Some say it was corny, but you be the judge. The old-school performance was completed by the three red-clad lady background singers in the ring.

Hopkins ended up winning a 12-round unanimous decision.


3) Naseem Hamed as Boxing’s Aladdin

When it comes to obnoxiously flashy ring walks, “Prince” Naseem Hamed is unparalleled in boxing history. With a knack for showmanship that far exceeded anyone else before him (or even after him), every Hamed ring walk was a theatrical gimmick ranging from the impressive to the absurd. Each production enraptured the crowd with creative exhibitions of horror, fantasy, and suspense.

While it’s definitely hard to pick just one, let’s single out one of Hamed’s craziest ring entrances to add to this list.

In March 2000, Hamed went up against Vuyani Bungu in London. Coming out with shades of Disney’s Aladdin, the “Prince” flew high up on his suspended magic carpet as he looked down upon the masses. The only thing missing was the song, “A Whole New World” playing in the background, but if someone suggested it to him, it would perhaps have been added.

With Hamed’s ascent to the heights of Olympia London, he set the bar at a level that we can confidently say no one else will ever reach.


4) Deontay Wilder’s Ring Walk Made Him Lose

The most recent entry on this list is the highly-anticipated Deontay Wilder-Tyson Fury rematch of February 2020. At the time, Wilder was coming into his own as the next biggest heavyweight boxing superstar following victories over Dominic Breazeale, Luis Ortiz, and Fury himself.

He was getting so comfortable in the limelight, that Wilder started putting together some insane ring walks, establishing his personal tradition of showmanship with ornate statement pieces.

Against Fury, Wilder dazzled the crowd with surreal skull-embellished, gem-encrusted black leather armor complete with LED highlights. The body armor weighed about 40 pounds alone, headpiece not included. At the height of impracticality, he wore that hefty dress for more than 15 minutes before he even walked down the ramp in an elaborate, drawn-out performance of a ring walk.

The ensemble was in tribute to Black History Month.

Reportedly, his legs were basically dead by the time he got inside the ring. Fury ended up stopping Wilder inside the distance. Wilder, later on, blamed the gaudy costume for his demise.


5) Mike Tyson’s Legendary Ring Walk

Advancing technology paved the way for bigger, flashier, and more elaborate productions, but there is no denying that the classics will always have a place in our hearts. With the legendary “Iron” Mike Tyson, less was definitely more. Tyson has one of the most memorable ring walks ever, with silence being the most impactful element.

It has been over two decades since he faced off against Michael Spinks, but his legendary ring walk that brought shivers down audiences’ spines remains clearly embedded in everyone’s memories.

Iron Mike’s ring walk is certainly the most intimidating on this list. With only the low hum of the crowd as his background music and the occasional sound of jangling metal, the heavyweight champion made his way across the crowd, surrounded by his entourage.

Tyson’s killer reputation and sheer force of presence alone were what amped the intimidation factor to the max.

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