Characters In On the Joke Shawn Levy

Phyllis Diller Character Analysis: The Positive Thinker

Overview

Phyllis Diller (1917–2012) is one of the central figures in Shawn Levy’s In On the Joke, profiled in the chapter “Five: The Positive Thinker.” Levy presents Diller as the first female superstar of stand‑up comedy, a woman who built a career from scratch in her late thirties while raising five children. She invented a “mad housewife” persona, complete with a fictional lazy husband named “Fang,” a cackling laugh, and garish stage clothes. Her story illustrates the book’s core themes of self‑invention, persistence, and the struggle for female comedians to be taken seriously in a male‑dominated field.

Plot Role in In On the Joke

Levy uses Diller’s biography to show how a woman with no role models could create a path to stardom through sheer will and positive thinking. Her chapter follows the book’s pattern: a difficult start, a long grind, a breakthrough, and the price of fame. Diller’s success is contrasted with earlier comedians like Jean Carroll, who faced similar obstacles without achieving the same level of recognition. Levy argues that Diller’s persona—attacking her own domestic failures rather than men—allowed her to win over audiences while still challenging gender norms. Her career peaks in the 1960s with network TV appearances and a Bob Hope film, but she also experiences failure with a short‑lived sitcom and a turbulent marriage. Ultimately, Diller’s arc underscores the book’s argument that pioneering women “created the cracks in the glass ceiling.”

Motivations and Traits Shown Through Actions

Levy attributes Diller’s drive to a belief in self‑help inspired by Claude Bristol’s book The Magic of Believing. She decided she could become a comedian after seeing Jorie Remus perform, even though she had no experience beyond amateur piano playing. Her actions demonstrate relentless persistence: she bombed repeatedly at the Blue Angel but returned to her dressing room each night to analyze what went wrong. She timed her sets with a stopwatch and constantly revised her material. Despite early rejections from The Tonight Show bookers, her pianist Harold Fonville called them daily until they relented. Diller also showed business savvy, soliciting jokes from the public for five dollars each and amassing a card catalog of over fifty thousand jokes, later donated to the Smithsonian. Her perfectionism is evident in her dissection of word choices: she insisted on “Jell‑O with a belt” instead of “Jell‑O with hair” because “belt” was a “pow word.”

Chronological Arc

  1. Early Life (1917–mid‑1930s): Born in Lima, Ohio, to older parents. Frances Driver, her mother, was a hardworking housewife who encouraged Phyllis’s musical talents. Phyllis took piano and singing lessons from age six.

  2. Marriage and Poverty (1930s–early 1950s): She married Sherwood Diller and had five children. The family struggled financially; at one point they lost their house and split up the children, sending some to live with Sherwood’s mother.

  3. Discovery of Comedy (mid‑1950s): Inspired by Claude Bristol’s book, she began writing comedy. After seeing Jorie Remus perform, she started doing stand‑up. She developed her “mad housewife” persona and the character of Fang.

  4. Purple Onion Run (c. 1955–1957): She performed for twenty months at the Purple Onion in San Francisco, evolving from a nervous beginner into a skilled comedian. She adopted the cackle, the cigarette holder, and the flamboyant wardrobe.

  5. Breakthrough (1958–1962): After a failed Groucho Marx show appearance and a disastrous Blue Angel run, she auditioned for Jack Paar’s Tonight Show in October 1958. Paar raved, and she became a regular, appearing more than twenty‑five times. This made her a national star.

  6. Peak Fame and Hollywood (1962–1968): She signed with major agents, appeared on The Ed Sullivan Show, made a cameo in Splendor in the Grass, and co‑starred with Bob Hope in Boy, Did I Get a Wrong Number! She starred in the sitcom The Pruitts of Southampton (later The Phyllis Diller Show), which was critically panned and canceled after one season.

  7. Later Career (1970s–2000s): Diller continued touring, writing books, and making TV appearances. She remained active into old age, still performing and being interviewed about comedy theory.

Relationships

  • Sherwood Diller (husband): The real‑life model for Fang. Levy depicts Sherwood as financially irresponsible, jealous, and unfaithful. He managed Phyllis’s early bookings but rarely attended her shows. The marriage was turbulent, with separations and reconciliations. Despite his flaws, she never divorced him, and he continued to appear as a guest in her act.
  • Warde Donovan (lover): While performing in New York, Diller had a long affair with singer Warde Donovan. The relationship contributed to her marital strain but also provided emotional support.
  • Irving Siders and Leonard Romm (career team): After her Paar debut, Siders became her personal manager and Romm her agent, guiding her bookings and helping shape her act.
  • Harold Fonville (pianist): Fonville’s persistence in calling Tonight Show bookers secured her audition. He played for her at one of her early New York clubs.
  • Joan Rivers (colleague): Diller treated Rivers as a peer when they worked together on Show Street, offering encouragement and respect.
  • Bob Hope (collaborator): Hope cast Diller in Boy, Did I Get a Wrong Number!, boosting her film career.

Key Decisions and Consequences

  • Decision to adopt the “mad housewife” persona: Diller consciously abandoned “chichi” material and wrote about her real life—housework, driving, husband—after realizing her audience responded better. This decision gave her an authentic voice and made her relatable to women.
  • Decision to dress outrageously: When figure jokes didn’t work because the audience could see she had a good figure, she started wearing shapeless, sequined dresses and crazy wigs. This created a memorable visual character that became her trademark.
  • Decision to buy jokes from fans: She offered five dollars for every joke accepted. This generated tens of thousands of pieces of material, which she organized in a card catalog. The consequence was a consistent supply of high‑quality one‑liners, but it also meant she relied less on original writing.
  • Decision to ask for more money to host Show Street: When the workload became unsustainable, she asked for a raise; the network balked and let her go. This preserved her energy but ended her TV hosting stint.
  • Decision to star in The Pruitts of Southampton: Despite misgivings about the show’s creative direction, she took the role. The sitcom was savaged by critics and canceled after one season, a rare failure in her career.

Themes and Symbol Connections

Levy connects Diller’s story to several themes explored on the companion site:

  • Self‑invention and persona: Diller literally created a stage character that exaggerated her own domestic struggles. She didn’t reveal her classical piano training or singing ability until her comedy persona was firmly established.
  • Persistence and resilience: From bombing at the Blue Angel to getting rejected by Tonight Show bookers, she never gave up. Her daily study of material after failed shows exemplifies this theme.
  • Gender discrimination in comedy: Diller faced the assumption that female comedians were unfeminine. She noted, “Being a woman, right away you walk out to almost total rejection. Almost nobody wants you to be a female comic.” Her success required overcoming that bias.
  • Censorship and double standards: Unlike comedians such as Belle Barth, Diller worked mostly without censorship because her material was self‑deprecating rather than profane. However, the double standard meant she had to avoid sexual topics that male comics freely used.
  • Trailblazing legacy: Levy argues that Diller’s pioneering career made it possible for later female comics. She “lived her life as an inspiration,” and her archive of jokes is now part of the Smithsonian.

Key Questions and Answers

1. How did Phyllis Diller develop her stage persona?

She based it on her own life as a housewife, exaggerating her domestic ineptitude and inventing a lazy husband named “Fang.” She adopted a cackling laugh and a cigarette holder to punctuate jokes. The persona was a “reductio ad absurdum” of her real situation, not genuine confession.

2. What role did Sherwood Diller play in her career?

He served as her early manager, negotiating bookings and salary, but he rarely attended her shows and contributed little financially. His failings as a husband provided material for her act, and they remained married despite his infidelity and her long affair with Warde Donovan.

3. Why did Phyllis Diller’s first TV sitcom fail?

The Pruitts of Southampton suffered from poor writing and creative interference. Diller felt ignored by the male producers, and the show was revamped mid‑season but still canceled after thirty episodes. Reviews were scathing, calling it “a forlorn item in every particular.”

4. How did Diller handle rejection and failure?

She treated failure as a learning opportunity. After bombing at the Blue Angel, she returned to her room to dissect each joke. She constantly revised material, timed her delivery, and sought outside gags. Her motto came from Claude Bristol: belief in oneself could overcome any obstacle.

5. What is Phyllis Diller’s legacy in In On the Joke?

Levy presents her as the first woman to achieve superstar status in stand‑up, proving that a female comic could headline major venues and TV shows. Her success inspired later generations, and her meticulous approach to joke construction influenced the craft of comedy. She left a physical archive that preserves her work for study.

Conclusion

Phyllis Diller’s character in In On the Joke embodies the power of self‑belief and relentless work. Shawn Levy shows that she was “more or less exactly who she said she was”: a suburban mother who willed herself into a legend. Her story is not just about laughs; it is about claiming space in an industry that told women they didn’t belong. By turning her domestic struggles into an act, Diller made the private public and changed American comedy forever. Her journey from poverty to wealth and acclaim, and her refusal to stop even when the show failed, makes her a quintessential example of the trailblazers Levy celebrates.