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The ‘Boxing vs. MMA’ Freak Show: A Video Timeline

When James Toney meets Randy Couture at UFC 118 next Saturday, he’ll be attempting to prove the dominance of the "sweet science" over that weird stuff that gay skinheads do. Of course, he won’t be the first pugilist to try to beat an MMA fighter at their own game — boxing vs. martial arts challenge matches have been around since before "Lights Out" was born. Join us as we take a look back at the brave boxers who preceded Toney…and what became of them.

December 2, 1963

Arguably the first sanctioned MMA match in American history, Savage vs. LeBell came together when legendary judoka/actor Gene LeBell answered a challenge from boxer Jim Beck, who claimed that a professional boxer could beat any martial artist. (Yep, they’ve been making the same boast for almost 50 years.) According to LeBell, he was expecting to fight Beck himself in the televised match, but his opponent was switched at the last minute to Milo Savage, a top-5-ranked light-heavyweight who was allegedly wearing brass knuckles under his fingerless speed-bag gloves, and was greased from head to toe. Despite the disadvantages, Gene sunk a lapel choke in the 4th round and put Savage to sleep. But as with most stories involving Judo Gene, the details are somewhat debatable; this Jonathan Snowden article debunks several aspects of LeBell’s version. Still, LeBell vs. Savage deserves credit as the first MMA-style fight on television, and set up a rivalry between boxing and martial arts that’s somehow still relevant today.

June 26, 1976

It sounded like good, harmless fun — the greatest boxer of all time taking on Japanese pro-wrestling kingpin Antonio Inoki in an exhibition match in Tokyo. But in the days leading up to the show, bizarre rules were added that restricted certain attacks. Most notably, Inoki could only kick if he had one knee on the ground. So, he scooted around the ring kicking Ali’s legs for the entire 15-round duration. Ali only landed six punches the entire fight and went home with two blood clots and an infection. The bout was ruled a draw, and has garnered a reputation as one of the ugliest fiascos in the history of combat sports. Fun fact: The referee of this match? None other than mixed-fighting pioneer Gene LeBell.

November 12, 1993

Art Jimmerson’s one-gloved appearance against Royce Gracie has become one of the defining images (and punchlines) of the UFC’s oddball early days. As the story goes, Jimmerson only accepted the fight because he was a little short on the down payment for his new house, and went in with no idea of what the Gracies were capable of. As soon as he got a crash-course in grappling from "Big" John McCarthy — and saw Gerard Gordeau kick Teila Tuli’s teeth out of his mouth in UFC 1′s opening match — Jimmerson wanted out. Still, he went through with the fight that he was clearly set up to lose, and tapped at the 2:18 mark, due to utter confusion. Two legends were built that day: Royce Gracie the submission wizard, and Art Jimmerson, the dude with one boxing glove who obviously didn’t belong there.

December 31, 2003

Dubbed the "King of the Four-Rounders" for his power-punching dominance in Toughman competitions, Eric Esch crossed over from semi-pro boxing to MMA at K-1 Premium 2003 Dynamite!!, and has found steady work in the sport ever since. But despite career MMA wins against such notables as James Thompson and Zuluzinho, his first appearance didn’t go so well, as he was out-grappled and submitted via heel-hook by Genki Sudo — who weighed less than half of what Esch did. Butterbean’s last boxing match was a split-decision loss last October, but his cage-fighting career is still chugging along. He’s slated to face Mariusz Pudzianowski at KSW 14.

June 23, 2007

With his boxing career fading, former WBO heavyweight champ and Olympic gold medalist Ray Mercer decided to pick up a paycheck by competing in an MMA exhibition for Cage Fury Fighting Championships against backyard brawling sensation Kimbo Slice. Mercer was expecting a slugfest, and didn’t prepare for anything else. Improbably, Slice muscled out two takedowns in the first minute and ended Mercer’s night with a guillotine choke from a loosely-closed guard. Not a happy ending for "Merciless" — but you can’t keep a good puncher down…

June 13, 2009

Two years later, Mercer was booked for the main event of Adrenaline III against former UFC heavyweight champ Tim Sylvia. Though Mercer vs. Sylvia was originally scheduled to be a boxing match, poor planning and athletic commission meddling conspired to turn the bout into an MMA match at the last minute. The fight itself lasted all of nine seconds. Sylvia only had time to throw one leg kick before Mercer launched an overhand right that felled Timmy like a big-bellied redwood. As Tim said after the fight, "It was the dumbest thing that I could have ever done. As soon as it was switched to Mixed Martial Arts I should have went in there and took him down and ended the fight in 30 seconds but I listened to his mouth run and I thought I could stand with a heavyweight boxer with four ounce gloves." Mercer’s analysis was more succinct: "I’m master of my game and his…You ain’t shit, Tim!"

Scheduled for May 15, 2010, then canceled

Having a former junior middleweight boxing champ face off against an MMA veteran like Din Thomas was interesting enough. But when Ricardo Mayorga showed up to the press conference, shit got real. Watch the above clip to see Mayorga give the Gettysburg Address of translated trash talk — which includes such revelations as what color towel he wears when he makes love to his wife — before karate chopping Thomas in the neck. That’s how you build heat, folks. Unfortunately, concerns about fighter safety and compensation — along with a well-timed injunction from Don King — nixed the event hours before it was supposed to go down, and Mayorga vs. Thomas is now just a footnote in the freaky history of boxing vs. MMA.

August 28th, 2010

After all the stalking, all the disrespect, all the amazing YouTube call-out videos, and all the questionable stories about choking out King Mo in training, it’s finally going to happen. Toney could catch a break next Saturday, like Ray Mercer did against Tim Sylvia. Or, he could be completely out of his element and tap at his first opportunity, like Art Jimmerson against Royce Gracie. As we’ve learned, anything can happen when a boxer meets a mixed martial artist in a cage — the only certainty is that somebody is going to get absolutely humiliated.


Cagepotato Comments

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Jaye Priest- August 22, 2010 at 10:04 am
@ fatbellyfrank, Me too bro!!! Except my parents used to get all the Tyson fights when i was younger(I'm 34) but man, I love those retro fights....classic.
fatbellyfrank- August 22, 2010 at 6:25 am
@ Jaye, I can remember watching that one with my Dad live via satellite!! Inoki just butt scooted for 12 rounds, it was a huge story back then, Dad used to let us kids watch all the big fights, and there where some pretty handy heavyweights around at the time, Ali, Frazier, Foreman, Norton, hell even ol Joe Bugner was a contender.
Jaye Priest- August 21, 2010 at 2:20 pm
Awesome videos!! Love the retro fights. That Ali/Inoki fight was bizarre.....Does anybody know if Gene Lebell is still alive????
Häkkiperuna- August 20, 2010 at 10:41 am

jimbonics Says:
Thu, 08/19/2010 - 03:42

Is Gene LeBell gonna hafta choke a bitch?

Love it.
daniel.mtl- August 19, 2010 at 5:41 pm
@DazedNConfused kung fu is best street-fighting martial art adapt to any environment and situation and there is muay boran which is muay thai kung fu
schizo310- August 19, 2010 at 10:42 am
I think all the bullshit came about because mma was such an entertaining event compared to a boxing card, boxing was losing popularity, and they just started slinging insults about how mma was gay and it wasn't real fighting. I don't remember any mma fighters saying that they could kick a boxers ass in the boxing ring. All this rivalry came from boxers just trying to keep their position in or culture. Well, shit happens and straight boxing is boring as fuck most of the time. Congrats mma on your success.
Nealio- August 19, 2010 at 8:02 am
Get off the weed DazedNConfused.

Your bullshit about streetfighters owning top professionals is ridiculous.
dranokills- August 18, 2010 at 6:25 pm
It's a shame the Mayorga vs din Thomas fight didnt happen. Din isn't much of a fighter or much of a MMA fighter, but he was still good enough to have put mayorga's stupid ass to sleep. after getting chopped(bitch slapped?) I think he really wanted to kill the stupid fucker. Woulda been a great bad.
As for mumbles, geez if he wakes up in the ring he will be lucky.
hes to slow, to fat, and to dumb, and Randy is just gonna make him even more "dain braimaged".
jimbonics- August 18, 2010 at 5:57 pm
the only certainty is that somebody is going to get absolutely humiliated.

Amen to that.
jimbonics- August 18, 2010 at 5:42 pm
Is Gene LeBell gonna hafta choke a bitch?
fatbellyfrank- August 18, 2010 at 4:58 pm
fatbellyfrank Says:
Thu, 08/19/2010 - 09:24
@ dazed and Rwilson, best thing for a street fight is a glock 9mm, puts a full stop on a lot of situations.
Pure sarcasm gents , IMO best thing in a street fight is good running shoes and a 10 second head start
Mr_Misanthropy- August 18, 2010 at 4:50 pm
@ Ben Goldensteinem

Good one. Ray Mercer was a beast in his day, some of the sweetest KO's I've seen from boxing. I still remember watching him knock Jeff Pegues out of the ring unconscious. He fell on the judges table.
mothercruncher- August 18, 2010 at 4:27 pm
This thread has gone all bullshido.
fatbellyfrank- August 18, 2010 at 4:24 pm
@ dazed and Rwilson, best thing for a street fight is a glock 9mm, puts a full stop on a lot of situations.
One thing in common with all these bouts is that they've all pretty much ended up as clusterfucks which only proves Boxing and MMA are very different sports with very different skill sets.
monkeyknuckler- August 18, 2010 at 4:21 pm
Yo. I got somethin' that'll knock you on yer ass without touchin' ya. But ya gotta be patient, 'cause Imma eat a burrito about a half hour before that happens.
RwilsonR- August 18, 2010 at 3:49 pm
@ DazedNConfused - Nuh-uh! The best martial art for anything is Tanaka Karate, as passed down by Senzo Tanaka. I had a friend of a friend who once did this, and he told me about this move they use called a 'dim mak' and you can kill a guy with one touch! So much better than Krav Maga.
DazedNConfused- August 18, 2010 at 3:40 pm
I was wrong in my previous post . While Muay Thai may be the best streetfighting style used in MMA, I'd have to say the best art to train in if you want to kick ass in 'tha streets' would have to be Krav Maga. I had a friend in that and he said you pretty much master how to kick people in the nuts and fuck with joints, eye gouge etc. It's bascially used to train people to get out of shitty situations.

A Krav Maga master could roll James Toney + Randy Couture, although those are two aged masters in both their respective sports.
One Two- August 18, 2010 at 3:22 pm
Sucks Don king shut down that fight, Kings a scumbag but sinking to danas level.
Under Banga- August 18, 2010 at 3:13 pm
Enjoyed the post ,thanks. Couple of observations;1 if the dude Gene fought was greased h2t ,it would have been very hard to get that Gi white ever again.2 Genes Judo looked like shit ! Pretty much like Karo don`t ya reckon?
DazedNConfused- August 18, 2010 at 3:12 pm
@ EvilScott

I agree I'd like to see an article like that, there are some good boxers in MMA.
DazedNConfused- August 18, 2010 at 3:11 pm
In a streetfight neither are particularly effective. It depends on the fighters skill set I guess, but a streetfight is still a streetfight. Knives, bottles, biting, kicks to the nuts, holding on/breaking fingers the fingers, using the environment. I have seen quite a handful of fights and a lot of those seemingly "unfair" tactics used.

The fact of the matter is, there could be people out on the streets who would fuck up most of the top MMA/Boxers on the street. That's a whole different ballgame just like Boxing and MMA are.

If I had to pick a fighting style best for streetfighting I guess I would say Muay Thai.
EvilScott- August 18, 2010 at 2:51 pm
How about a followup article with MMA fighters who have competed in boxing? I know Chris Lytle has a few matches, Marcus Davis boxed before MMA, Vitor had a boxing match a while back, etc.
CodyV- August 18, 2010 at 2:50 pm
I always figured the debate was which was the more effective way to fight. If a MMA fighter fought a boxer on the street with no rules. Since Toney and Randy are fighting in a MMA fight rather than boxing match, it seems to be closer to a real street fight.
DaltonSwayze- August 18, 2010 at 2:44 pm
HAHAHAHAHA you were 14 minutes late and you said "first"?????
joshuan29- August 18, 2010 at 2:39 pm
First dammit