The woman was a prolific actress, and very popular in her day. She did a little TV in the late '50s. (Perry Mason, Hitchcock) but I don't think she ever received Oscar recognition. That, of course, eliminates Bette Davis. Later I'll put up a better picture of her, full faced, so don't scratch out all your hair just yet, Spumoni.
The boy in the High School pic won an Oscar early on, but in 50 more years that was not repeated. Due to a Garfield-esque quality he acted in a lot of cops and robbers productions. His TV career was equally notable.
The last man struck out on the big screen, but was a hit on the small one. Some may look at that face and
immediately know. Others (like I) will be utterly confounded.
May I request that if you know one of these people right off, or was tempted to peek, add a subtle hint to keep the Signor in the hunt. Like I, he digs this stuff.