Since he was in Nothing But Trouble (1991), I'll go with Tupac.
Also, there is pretty significant correlation between him and George Michael right now.
*edit: I am just discovering some awesome mashup tracks:
https://youtu.be/Wn7RCc1mMds
I would prefer to listen to George Michael.
Tupcac is the more culturally significant.
My Vote: Tupac
As revered as both artists are, I'd say it's pretty telling how Tupac's music has resonated with successive generations while George Michael's late stage comeback album struggled with respect to previous critical and financial success.
Why not enjoy both? It's a shame we never got a live performance of this collaboration:
https://youtu.be/jDm9UPw_WDU
Not a fan of either one, but I'd have to say George.
shareGeorge Michael. I dont really think of Tupac as a singer at all.
shareObviously George
shareGeorge Michael.
shareTupac.
I don't own anything by either one but my very limited exposure to both makes me favor Tupac. Alas, Tupac also represents the wave of hiphop that lead me to lose interest in the genre.