i think it's just a "maybe" as to whether Diana would have achieved a pop hit in the 90s. You mention Tina, Cher and Patti but all 3 of them, frankly, had stronger public images in that people like them and their personality. they hadn't had the damning PR backlash that Diana experienced. They also had a bit of underdog on their side.
having a hot producer is also just part of it. they would have had to come up with something really compelling to generate interest. simply having DR sing a Luther or Babyface song wouldn't have done it, IMO. that could have been written off like a Mom trying to be young.
I wonder if a stronger return to film and tv wouldn't have done it. she was wonderful in Out Of Darkness. perhaps another project like that. or a big hit film. something that might help share her for comedic and personable side. Darkness displayed her talent but you don't walk away from it thinking "diana is just like me - we could be best friends!" like you would with a great comedy or a more fun movie.
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