3. Art Jimmerson
Weight: 196 pounds (89 KG)
MMA Record: 0-1
Another demi-legit athlete from the boxing world, Art Jimmerson is not a name known by too many modern mixed martial arts fans. Touting a professional boxing record of 29-5 and a former Golden Gloves champ, ‘One Glove’ as he would later become known decided to try his hand at the whole ‘UFC thing’ at the promotion’s first event in 1993. Entering the one-night tournament, Jimmerson had possibly the worst luck anyone could have had that night, facing the tournament’s eventual winner and future hall of famer Royce Gracie in the opening round.
Insisting on wearing a single boxing glove so not to hurt his jab hand, AJ faced a bare knuckled Jiu Jitsu black belt in what would turn out to be a humiliating affair for the pro boxer. He was taken down quickly and tapped out once the grappling master got to mount. One of the very few submissions to position, and the only ever fighter to wear a single boxing glove in the UFC octagon makes Art Jimmerson one of the original and most poignant freak show fighters ever.
He would never go on to fight in MMA again, but he went on to become the current boxing coach at the UFC gym in Torrance, Canada after retiring from boxing in 2002 with a 33-18 record. He has also recently expressed interest in fighting Kimbo Slice, so get ready for a shoot up to first place if that ever happens for Jimmerson.