Highlights

• Jake Paul vs. Mike Tyson: is a freakshow fight a spectacle for the ages.
• Boxing has a history of odd fights including a two-in-one bout with KSI.
• Impressive but bizarre fights have included former NFL vs NBA, Tonya Harding entering the ring.

Earlier this month, it was announced that Jake Paul and Mike Tyson will be colliding in July, on Netflix. The two boxers will clash up at heavyweight, in what is being targeted as a real professional boxing match. If the fight is sanctioned by the Texas State Athletic Commission as such, it will be Tyson's first real fight in nearly 20 years.

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No offense to the legendary 'Iron Mike', but everyone knows what this is. This is an absolute freakshow fight, due to the legend's advanced age, but it will genuinely be one the most-watched bouts of 2024. With that in mind, let's take a walk down memory lane and reflect on other freakshow fights.

10 Misfits Boxing 1: KSI vs. Luis Alcaraz Pineda and Swarmz

'The Nightmare' Fought Two Men In One Night

KSI	Swarmz	Luis Alcaraz Pineda
5'11"	5'8"	6'3"
179.9 Pounds	199 Pounds	179 Pounds
1-0 Record	0-0 Record	2-5 Record

We're starting off with a bit of a two-in-one entry. Influencer boxer KSI has become one of the biggest names in the sport, through unorthodox means. After nearly a three-year hiatus, he scheduled a return against Alex Wassabi for August 2022.

However, Wassabi withdrew weeks before the bout, and in-stepped Swarmz. However, KSI felt that the former footballer-turned-rapper wasn't a big enough test, and also fought journeyman boxer Luis Alcaraz Pineda. He dispatched of both men in one night, in an absolute freakshow event.

9 Anderson Silva vs. Tito Ortiz Was Downright Hilarious

Imagine Paying Tito Ortiz Money To Box

Anderson Silva	Tito Ortiz
6'2"	6'2"
192 Pounds	200 Pounds
2-1 Record (34-11 MMA)	0-0 Record (21-12-1 MMA)

Triller Fight Club might be the oddest boxing promoter of all time. The upstart company largely backed by venture capital money brought fans such as Jake Paul vs. Ben Askren, inter-spliced with several concerts and comedy skits. Yeah, they were mostly terrible. In 2021, the company had the most odd double-header of all time.

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A nearly 60-year-old Evander Holyfield fought Vitor Belfort in an exhibition main event, while Anderson Silva faced Tito Ortiz in the co-main professional bout. The latter gets the nod for this entry though because paying 'The Huntington Beach Bad Boy' for a boxing match is hilarious. He was predictably finished in round one.

8 Uriah Hall vs. Le'Veon Bell Was Incredibly Random

They Fought On The Undercard Of Jake Paul vs. Anderson Silva

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Jake Paul's undercards have become home to fights even odder than the ones that he's in. In October 2022, 'The Problem Child' faced Anderson Silva, with an incredibly bizarre pro fight on the undercard.

Uriah Hall was actually the man who sent 'The Spider' packing from MMA and faced former NFL running back Le'Veon Bell on the undercard. Predictably, 'PrimeTime' scored a lopsided decision win.

7 Roy Jones Jr. vs. Anthony Pettis Didn't Need To Happen

'Captain Hook' Was 54 Years Old In This Bout

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Anthony Pettis	Roy Jones Jr.
5'10"	5'11"
198.5 Pounds	199 Pounds
0-0 Record (25-14 MMA)	66-9 Record

This fight really flew under most fan's radars. In April 2023, the great Roy Jones Jr. ended a five-year retirement for a professional fight with former UFC lightweight champion Anthony Pettis. Much like the boxer, 'Showtime' was years past his best, and fighting way above his weight class.

Still, this fight was forgotten because it was a slow, sluggish affair. This bout resembled a sparring session more than anything and ended with Pettis getting a split-decision win.

6 Floyd Mayweather vs. Conor McGregor Was The Perfect Spectacle

'Money' And 'The Notorious' Fought In 2017

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Floyd Mayweather	Conor McGregor
5'8"	5'9"
149.5 Pounds	153 Pounds
49-0 Record	0-0 Record (21-3 MMA)

There are few fights throughout history timed better than Floyd Mayweather vs. Conor McGregor. In 2017, 'Money' was retired, but just about everyone knew that he badly wanted a 50th win. At that same time, 'The Notorious' was the biggest combat sports star alive, and a two-weight UFC champion.

They reached a deal to fight that August, and they promoted it perfectly. As far as the action itself goes, while the Irishman had a nice start, he quickly gassed out. Mayweather wound up battering McGregor down the stretch, earning a 10th-round stoppage win. The fight itself went on to gross an incredible 4.3 million pay-per-view buys, the second most in boxing history.

5 Tonya Harding vs. Samantha Browning Was On The Undercard Of Mike Tyson's Final Win

'Bad Girl' Went Into Boxing After Figure Skating

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Samantha Browning	Tonya Harding
5'4"	5'1"
123 Pounds	123 Pounds
0-0 Record	0-0 Record

Many likely don't know, but Tonya Harding, yes the controversial figure skater, years after her legal issues. In 2003, decided to make her professional debut after a one-off celebrity boxing match. Harding got the chance to make her debut on the undercard of Mike Tyson vs. Clifford Etienne.

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'Iron Mike' scored his final win that night, scoring a first-round knockout. Meanwhile, Harding was less lucky, losing a split decision to fellow debutante Samantha Browning.

4 Hafpor Bjornsson vs. Eddie Hall Was The Heaviest Boxing Match Ever

'The Mountain' Won By Unanimous Decision

Hafpor Bjornsson	Eddie Hall
6'9"	6'3"
335 Pounds	313 Pounds
1-0-2 Record	0-0 Record

In November 2020, a fight between Hafpor Bjornsson and Eddie Hall was announced. The bout was targeted for July 2021, but wouldn't happen for another year. Finally, the two fought in Dubai in March 2022, in the heaviest professional boxing match ever.

Well, for the time, the record was later broken by a Misfits Boxing match. Nonetheless, 'The Mountain' largely dominated this fight, scoring two knockdowns en route to a unanimous decision victory.

3 Frank Gore vs. Deron Williams Was NFL Vs. NBA

These Two Fought On The Undercard Of Jake Paul vs. Tyron Woodley II

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Deron Williams	Frank Gore
6'3"	5'9"
211.2 Pounds	209.6 Pounds
0-0 Record	0-0 Record

Again, Jake Paul really likes booking bizarre fights. On the undercard of his rematch with Tyron Woodley, he scheduled a boxing match between former NFL running back Frank Gore and former NFL All-Star Deron Williams.

The two put on a really good fight, as they had both boxed regularly for fun for a few years. In the end, it was the former basketball player who claimed a split-decision win after four rounds.

2 Larry Holmes' Retirement Fight Against Butterbean

The Legend Fought 'The King Of The Four Rounders' In 2002

Larry Holmes	Eric 'Butterbean' Esch
6'3"	5'11"
254 Pounds	334 Pounds
68-6 Record	65-3-3 Record

This is another fight that's hard to believe actually happened. In 2002, the 52-year-old legend Larry Holmes was looking for one final bout. He decided to face super-heavyweight star, Butterbean. To that point, his longest fight had been six rounds.

However, Butterbean took the legend the full ten-round distance in their heavyweight bout. While Holmes picked up the win, the super-heavyweight got a moral victory in the form of a knockdown in the last round.

1 Jake Paul vs. Mike Tyson Will Be A Spectacle For The Ages

It Probably Shouldn't Happen, But It Is

Jake Paul	Mike Tyson
5'11"	5'10"
199.75 Pounds	220.4 Pounds
9-1 Record	50-6 Record

Alright, a 57-year-old Mike Tyson likely shouldn't be fighting under any circumstances. But, 'Iron Mike' is a legend, and it's hard to control what he does unless a boxing commission gets in his way. On July 20th in Dallas, he will meet Jake Paul in front of 80,000 fans in AT&T Stadium.

The bout will be streamed on Netflix, and given the wide-viewer base, and lack of PPV added to the Netflix subscription, the fight has the possibility of becoming the most-watched fight ever.