Conquering My Dislike of Shakespeare to Master Jeopardy

If you’ve ever watched Jeopardy, you know that Shakespeare is a popular and recurring category. Unfortunately for me, I don’t like Shakespeare. Never have. Yet, if I wanted to increase my chances of winning on Jeopardy, I knew I needed to buckle down and learn it.

I tried — and failed — several times before I finally found an approach that worked. Here’s a recap of my journey and what ultimately led me to success.

Attempt #1: Read Every Play Summary + Flashcards

My first approach was pretty straightforward. I would read the plot summary for every single Shakespeare play, then drill myself with flashcards made from hundreds of past Jeopardy questions about Shakespeare. My logic was simple: if I could memorize enough content, I could brute-force my way to Shakespeare mastery.

It didn’t work.

The information didn’t stick. I couldn’t keep the plays straight, and the flashcards became a blur of names, plots, and unfamiliar words. I realized quickly that I needed a different approach.

Attempt #2: Summary + Video + Quiz + Flashcards

Next, I tried a more multi-sensory approach. For each play, I would:

  1. Read a plot summary of the play.
  2. Watch a video summary to get a feel for the language and pronunciation.
  3. Take a quiz to test my understanding.
  4. Drill flashcards based on past Jeopardy questions.

I thought adding the video component would help with pronunciation and provide more context for each play. And the quizzes were helpful in seeing if I actually retained anything.

But ultimately, I still fell back into the trap of cramming with flashcards. It was too much. Too overwhelming. I still couldn’t differentiate the plays in my head. Once again, I knew this method wasn’t working.

What Finally Worked: Break It Into Chunks

The key to finally making progress was breaking it down by play type. I realized I was trying to consume too much at once. So instead of approaching all 37 plays at once, I broke them down into categories:

  1. Tragedies
  2. Comedies
  3. Histories
  4. Other

I started with tragedies. I re-read the plot summaries, watched videos, and carefully reviewed a smaller subset of flashcards — only tragedy-related questions. This smaller scope made the information more manageable, and I slowly built my confidence.

Once I felt solid on tragedies, I moved on to comedies and repeated the process. Then I tackled histories. Finally, I studied the other plays.

The big difference was that by focusing on one type of play at a time, I was able to keep the characters and plots from blurring together. I finally started to feel confident answering Shakespeare-related questions.

Why This Approach Worked

  1. Chunking the information kept it from becoming overwhelming.
  2. Watching the videos was crucial for learning how to pronounce character names and key plot points.
  3. Targeted flashcards (only tragedies, only comedies, etc.) allowed me to build mastery in stages.

This approach didn’t make me like Shakespeare any more than I did before. But it did make me better at Jeopardy — and that was the goal.

So if you’re like me and dread Shakespeare but still want to crush those Jeopardy questions, my advice is simple: break it down into manageable chunks, focus on one play type at a time, and don’t underestimate the power of watching video summaries. It might not turn you into a Shakespeare fan, but it will make you a better trivia player.

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