Crossword puzzle clue "she's ahead of her time"

She's ahead of her time

Comedian who married Joyce Mathews in 1941, divorced her in 1947 and married her again in 1949 "because she reminded me of my first wife"

"See, how she leans her cheek upon her hand!" speaker

She had her first and only child in her 90s

2004 Ashlee Simpson hit in which she expresses her desire to sing a song she doesn't know the lyrics to with someone in the kitchen on the floor

"People say she's crazy, she got diamonds ___ of her shoes"

Nevertheless, she asked him if he had attended her high school, and after he said yes, she asked "...?"

"She's beauty and she's ___, she's Miss United States!" (introduction I'm sick of! I'm just a regular guy now)