Forget about the fights themselves, you are just trying to make interesting press conferences. Lets say that you get to do "the gloves are off" as well. You can match fighters from different eras, but the matches have to be realistic in terms of weight class.
James toney and Mike Tyson would be insane and I'd pay to see it. Ali and jack Johnson Shannon Briggs and Tyson Fury (make it happen!) Duran and Mayweather Mayorga and Canelo
Roberto Duran vs Griffith/Don Curry Panama Al Brown vs Vic Darchinyan Joe Calzaghe vs Carl Froch Riddick Bowe vs Derick Chisora Muhammad Ali vs Mike Tyson James Toney vs Jake LaMotta Max Baer vs David Haye Gervonta Davis vs Jorge Paez Connor McGregor vs Mayorga Fury vs Briggs would be incredible
Roberto Duran vs Ricardo Mayorga: I wouldn't understand a single word but it would still be legendary Muhammad Ali vs Mike Tyson Shannon Briggs vs Derek Chisora Jermell Charlo vs Tony Harrison III Jean Pascal vs James Toney
Chris Eubank v Archie Moore - listening to both of them pseudo-philosophise on the fight would be great fun.
Muhammad Ali & Tyson Fury Mike Tyson & Deontay Wilder Adrien Broner & Ricardo Mayorga Antonio Margarito & Ricardo Mayorga
Both strike me as men who would not use more force then necessary on someone they like. I feel as if they would be friends by the time of the fight and we would get a sparring match.
Broner vs Barkley has been mentioned. I would just like to say if Broner humped Iran he would literally be vaporised into a puddle of blood to the sound of cheers.