For years, Perry Diller had a regular Monday lunch date with his mom, the legendary Phyllis Diller. Now, Phyllis was no ordinary cook—despite her jokes about being terrible in the kitchen, she was actually pretty great. But she had a mischievous streak that loved testing her son's limits. "She knew how much I hated anchovies," Perry told Closer. "She’d make me a salad, and under the lettuce, she'd sneak in three strips of anchovies. I’d say, 'Mom, you’re a lunatic!' but she’d just laugh so hard she couldn’t breathe." It was their thing, a playful ritual that kept them connected.

Despite her antics, Perry feels incredibly lucky to have had Phyllis as a mother. The trailblazing star, who became one of the first nationally famous female comedians, grew up in Ohio dreaming of a career in classical music. Life took a different turn when she eloped with Sherwood Diller, her brother’s friend, and became a mom to five kids. "My dad wasn’t exactly Mr. Reliable," Perry admits. Sherwood struggled with agoraphobia, which often left him unemployed. But he had faith in Phyllis. "When Milton Berle signed a million-dollar contract with a TV network, Dad told her, 'You’re just as funny. You could do that too.' And she listened," Perry says. That encouragement planted the seed for her incredible journey.

Phyllis found her strength in The Magic of Believing, a 1948 book about positive thinking by Claude M. Bristol. It was life-changing for her. "From here on, it was straight up, all the way," she wrote in her 2005 memoir Like a Lampshade in a Whorehouse: My Life in Comedy. "Everything I touched would turn to gold." That optimism fueled her rise, but it wasn’t easy. Back then, the world of stand-up comedy was almost entirely male-dominated. "As a kid, I saw some guy try to trip her as she walked onto the stage," Perry recalls. "The clubs were rough—full of drunks, and everyone smoked. It was like walking into a gray cloud."

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Being on the road meant missing her kids. "For a couple of years, we lived with family in St. Louis until my mom started making money," Perry explains. "They lived in this tiny, crummy apartment above a liquor store. But once she hit it big, things changed." With her wild bleached hair, oversized dresses that hid her slim figure, and that iconic jeweled cigarette holder, Phyllis introduced herself to America as the ultimate housewife from hell. Her jokes about her "useless husband Fang," her awful in-laws, her appearance, and her lack of domestic skills were punctuated by her signature cackling laugh. She became a pop culture icon and divorced Sherwood in 1965.

Phyllis Diller Took Friend Barbra Streisand Under Her Wing — Silver Screen Collection/Getty Images

Once she started earning, she made it her mission to reconnect with her kids. "Mom bought a house," Perry says. "I went from sleeping on a cot to having my own room with a bunk bed so I could invite friends over. Growing up, she wasn’t around much because she was working so hard, but she was always my best buddy." Phyllis didn’t just build a career; she built a family life that mattered deeply to her.

Phyllis Diller’s Legacy: A Lifelong Love for Friendship

Early in her career, Phyllis earned the support of comedy greats like Bob Hope, Jack Paar, and Johnny Carson, who became lifelong friends. "My mom was the most loyal, generous friend you could ask for," Perry says. He remembers how Phyllis took her opening act, a young singer named Barbra Streisand, under her wing. "Mom bought her clothes," Perry says. Other close friends included Tom and Dick Smothers, Laugh-In producer George Schlatter, and Betty White.

Phyllis and Betty had a playful rivalry for the best table at their favorite little French café in Brentwood, California. "If the other person got the table, they’d walk past and give each other the finger," Perry recalls with a laugh. "Then they’d burst out laughing and make silly faces at each other. They were just so much fun to be around."

Phyllis Diller’s Diverse Career and Personal Life

Phyllis’ career spanned nightclubs, recordings, TV, movies, Broadway, and even several books. In the '70s, she performed classical concert piano under the pseudonym Dame Illya Dillya. Later in life, she discovered a passion for painting. "She had such a full, complete life," Perry says. "Creatively, she touched every base." And her personal life was just as rich. After remarrying, Phyllis found lasting love with Robert Hastings, her longtime companion. "He was the best," Perry says. "Kind, funny, and he adored Mom. They were soulmates."

Of course, life wasn’t always easy for Phyllis. She lost Robert in 1996 and outlived three of her children. But even in her later years, she remained a beacon of positivity. "She didn’t want to share her negativity with anyone, especially her family," Perry says. "Even after her passing in 2012 at age 95, I still miss our lunches. We’d play 'Diller’s Gin,' a twist on gin rummy, and laugh so hard the whole house could hear us. Her home was always filled with joy and humor."