A lot of weird variables and circumstances with both guys, so it's tough to say, exactly. Here's what I know for sure:
Wherever you rank Floyd, you probably need to rank Roy higher. There's no way to look at their first 50 fights and come away thinking Floyd is the better or more accomplished fighter.
Roy could have called it quits after Ruiz... or even after Tarver 1... and he'd have been hailed a top 5 P4P fighter forever. He kept fighting and that hurt him. But the truth is, he sacrificed his dominance in order to go up in weight and win that HW strap. He came back down too suddenly, was slower and softer, and paid for it. Doesn't detract from what he was for 50 fights up to that point. Not 20 fights. Not 30. 50. That's a career.
Eh, I think you can come away, easily thinking Floyd is better and more skilled. Roy is definitely more athletic, and probably the most athletic boxer ever. However, he did a lot of stuff you're not suppose to do, which is why he ended up getting KOed a bunch of times. Floyd was both very athletic/talented, and much more skilled.
I would have Roy in the top 10-20, Floyd in the top 5... Tyson in the top 50.
If you look at Roy's first 50 fights, up against Floyd's 50 fight career, the KOs post Ruiz don't factor in. It's hard to say what we'd see from Floyd if he continued to fight top level competition right now, because he stopped fighting at the point in his career where Roy started losing. Assuming he'd win fights that he won't even take is an odd way to justify giving him a higher ranking, in my opinion.
Even the first 50 fights are not as good as Floyd's first 50. Floyd fought more champions, who were champ/belt holders at the time of the fight, and has the best compubox stats. Even back during his prime, Roy got a lot of criticism for his opposition, much more so than criticism Floyd got (who also got/gets a lot)
edit: I also feel Floyd's performances vs Chico, Gatti, N'dou, even vs Canelo, as visually as impressive as any of Roy's
The Canelo fight is the only thing that makes it close to me. Roy's offense, combined with his jump to HW (precisely because there just wasn't anything very challenging for him in the lighter weight classes), and the fact that Floyd really did wait on a lot of fights until the timing tilted much more in his favour, makes it really hard for me to put Floyd at any better than a virtual tie with Roy.
What clinches it for me is that Roy took on Ruiz at about the same point in his career as Floyd took on Conor. I get that it was a massive money fight and anyone would have done the same. But that doesn't change the fact that there's still no way to stack it up in comparison with jumping to HW and grabbing a belt.
Then Floyd fades away and Roy keeps fighting top competition and gets KOd.
They are both legendary fighters of our era and great champions. IPT they both deserve to be in the top10 all time boxer's list. How do rank these two boxers?
Lol wut? Jones was like 34 or something when he fought Ruiz. That is when Floyd was fighting Cotto, Canelo, Mosley, Pac. Maidana.
So you could say that at the same point of their career, Roy was getting KOed and fighting people like Trinidad who had not fought on 2 years.
Floyd faught Conner when he was like 40 or 41, which is around whe Roy was getting Koed by Danny Green
I dont think anyone but you would have Tyson in the Top 10. Jones Jr. is probably Top 20 but not Top 10 imo.