The funny thing is that I really don't equate her with Marilyn Monroe other than the Playboy centerfold.
It is probably the difference of the times but Monroe had the wink-wink sexiness that lured men in and excited their fantasies while remaining very feminine. By the 1990s, Smith had to be more like Madonna than Marilyn to get the attention she craved. What Marilyn did wouldn't get much attention today - not with all the porn on the internet and the unsubtle sexuality of our modern times.
BTW, this makes at least six former centerfolds to die young:
Marilyn Monroe
Jayne Mansfield
Claudia Jennings
(name escapes me but she turned to prostitution in Florida)
Dorothy Stratten
Elisa Bridges
Anna Nicole Smith
There could be others I'm not aware of.
Actually I would think Anna looked more like Jayne Mansfield.