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4. This 1992 painting by L.A. artist Cynthia Janet White
The subjects mostly have theirs backs to the viewer -- but are they giving us the thumbs up sign?
3. This pencil drawing of Oprah
It seems to have been made around 1994 judging by the hairdo, which resembles Jennifer Aniston's "Rachel" cut.
2. This pastel-colored portrait of Oprah
The hair, once again, is the focus of the image. We'd be willing to wager that this iconic hairstyle and pink turtleneck look dates back to the late 1980s.