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National Boss's Day

Celebrate National Boss's Day on October 16th with this trivia game on the worst bosses from TV, movies, music, and more.

15 questions · Published October 19, 2026

Trivia questions (5 of 15)

  1. Multiple Choice

    1. Which of these musicians is Bruce Springsteen, known widely by his nickname "The Boss"?

  2. Multiple Choice

    2. In what fictional city can you find this cruel boss of the local nuclear power plant?

  3. Multiple Choice

    3. On what show is this tough, but secretly sweet, boss of surgeons and residents found?

  4. Fill In The Blank

    4. According to the name of the show, this TV boss works at the New York City address: __ Rockefeller Plaza.

  5. Multiple Choice

    5. What is the name of the fictional fashion magazine that this boss rules with an iron fist?

10 more questions in the full game

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