To make it fair, you would have to take the best of Tom vs. some fractional percentage of "the best version of" the Pride fighter, depending on the degree of PED use in question. A straight comparison without adjustment gives the PED guys an artificial boost.
To answer the OP's question (I don't think ring vs cage matters much in this particular hypothetical), chunked out by his tiers:
1. Nukes everyone in the "notables" list.
2. Has favorable but competitive fights against Sergei and Werdum (Pride version).
3. Has favorable and "fun" fights against Henderson (Pride version) and Alexander (meaningful favorite in both)
4. Beats Fujita, Randleman, and Coleman handily. Stylistic advantage ++
5. Beats Herring cleanly. Beats Bigfoot (SF version?) from movement and speed.
6. Beats a PED free Wanderlei with moderate difficulty (size would matter).
7. Barnett is interesting to think about, and probably the fight I would be most interested in seeing. I don't have a good sense of it.
8. Cro Cop would force him to stand even if Tom tried to move it off-feet. Close to a pick em' IMO. If Tom could pressure and press Cro Cop, it might lean more in his direction.
9. I'm not as confident as some of Big Nog's ability to get some combination of TD and submission on someone who moves like Tom combined with a higher degree of BJJ understanding (at least defensively) than the supermajority of Nog's opponents he got sub wins over. I would be inclined to pick Tom gun-to-head. I don't think Nog's game would age well in the modern era vs. top big fighters.
10. Loses straightforwardly to Fedor Pride version who mixed grappling and strategic/intelligent striking beautifully. Beats the later version of Fedor who mostly headhunted with wild power strikes.
That is how I think things would trend, be the general pattern, probability, etc...