She was a pioneer - at one time Diller operated seven separate companies: PhilDil Productions, Phyllis Diller Theatres, Rockingham Productions, Diller Art, Phyllis Diller Creations, Philli Dilli Chilli, and La Vie Beauty Products. In 1990, she was named Celebrity Businesswoman of the Year. "I'm only called in for making big decisions," she once told entertainment reporter Vernon Scott. "I'm good at making up my mind. I say a bad quick decision is better than a good slow decision." For years, concerts brought in lots of income; after that came jewelry and art work. Some time back, the New Yorker's Tad Friend visited Diller at her Brentwood home:
Diller moved into her house, a ten-thousand-square-foot stucco affair, in 1965, after leaving the first of two unhappy marriages. She was America's most famous female comedian, a fixture in Bob Hope movies and on television specials, where she often played a kooky, gaudily costumed housewife. In those days, Judy Garland lived just up the street. Then came the "Gong Show" years, and, as Diller's bookings dried up, she began to paint. Late at night, she'd throw on a pink smock, put some Gershwin on the stereo, and work up an ink or acrylic sketch of a castle, a few dailies, or Alex Trebek. In 2003, when she was eighty-six, she began holding "art parties," several times a year, to sell the work, along with her outfits and her costume jewelry. She explained, "I'm only leaving here toes up - I'm not going to any home for old ladies - and I'm not taking anything with me!