Issa Rae MasterClass Review: Worth it? [Must Read Before Buying]

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Who amongst us has not spent days binge-watching TV series or film series? We have all been there and done that (no shame or judgment). There is just something compelling and appealing about good cinema that you can not turn away from.

As a drama major, I have always aspired to do that. But my head is full of daydreams, and my notebooks are full of half-written screenplays. I watch award shows as if I were nominated—but not for the reasons you might assume. I religiously watch all award ceremonies to hear the acceptance speeches (looking at shots of Timothee Chalamet is just a bonus).

While watching one late award show, with my greasy hair and popcorn bucket in tow, I came across Issa Rae. I am kind of ashamed to admit that I did not know her. I quickly looked her up and found out she was the creator and star of “Insecure.” As she won the Black Girls Rock ceremony award, I was looking up everything I could about her. I also watched “Insecure” in one sitting and was completely floored.

My extensively detailed internet search (cue stalker music) on Issa Rae led me to her MasterClass, and I immediately scrambled to sign up.

I learned Issa Rae is not just an average actress I would fangirl over; she is my creative kindred spirit. Her work is honest, hilarious, and unapologetically Black. As a person of color, I crave to bring life to the kind of characters that push the boundaries of cinema and reflect the world around us in all its messy glory.

So, yeah, when the opportunity arose to learn from the queen herself, well, let’s say my credit card practically tapped itself. This review of Issa Rae’s MasterClass is a breakdown of what a drama major with a case of Issa Rae-idolism learned from the mastermind behind “Awkward Black Girl” and “Insecure.”

Let’s get this (virtual) camera rolling!

Issa Rae MasterClass Quick Overview

If you are short on time, here is a quick summary for you to go through.

You’ll learn how to:

  • Work in the entertainment business
  • Construct compelling stories
  • Develop iconic television characters 
  • Highlight cultural diversity in your writing
  • Manage your online and social media presence
  • Write and pitch stories for films and series 

Time Duration 

This class is 2 hours 17 minutes long.


  • Learn from an inspiring artist 
  • Well-structured and balanced course
  • Opportunity to learn about Issa’s beginnings 
  • Suitable for all skill levels
  • Charming screen presence and a friendly teaching approach


  • The class is a little short
  • Conversational style of teaching might not be suitable for everyone

Best to pair with:

If you are interested in screenwriting, you may enjoy Shonda Rhimes’ MasterClass on writing for television and Aaron Sorkin’s MasterClass on screenwriting.

If acting is your calling, then you will appreciate Natalie Portman’s MasterClass on acting and LeVar Burton’s MasterClass on the power of storytelling.

If you find creative writing appealing, you will prefer Dan Brown’s MasterClass on writing thrillers and Margaret Atwood’s MasterClass on creative writing.


We all know people of color are underappreciated and overlooked in the entertainment industry. Issa Rae’s MasterClass provides a fresh perspective on dealing with that while being true to your craft. If you are a movie bug, aspiring actor, or screenwriter, you will learn a lot from this MasterClass.

Issa Rae MasterClass Review

Who is Issa Rae?

Issa Rae is an award-winning actress and creative force who has carved her own path in the entertainment industry. She acts, writes, and directs (what can this woman not do?), so you can say she is a Jack of all trades.

Issa started her acting journey with a small web series, “Awkward Black Girl,” a project she created and performed singlehandedly. As a Black person, the lack of representation in media always rubbed Issa the wrong way, and she had a strong desire to showcase the stories and struggles of people of color in the mainstream media. Her web series went viral, and Issa became an overnight success.

Issa’s fame caught HBO’s attention, leading to the critically acclaimed series Insecure, which she co-created, co-wrote, and starred in. “Insecure” lasted five seasons and won numerous awards, establishing Rae as a powerhouse of talent.

Rae is an immensely talented actor who was nominated for a Golden Globe Award for Best Actress in a Television Series—Musical or Comedy—and multiple Primetime Emmy Awards for her work on “Insecure.” Moreover, she has received recognition from the NAACP Image Awards and the Black Girls Rock! Ceremony (where I first came across her), and countless other organizations.

Beyond acting and writing, Issa Rae has also served as a producer on various projects. Her experience and expertise transcend skill sets. She has done everything from creating compelling characters to navigating the difficulties of production. Issa’s well-rounded background allows her to share valuable insights across different aspects of the entertainment industry.

So, what makes Issa Rae the ideal host for a masterclass in writing and acting? 

Rae started as a digital content creator and now leads TV shows. She understands the challenges and victories of exploring the entertainment industry. Her work is known for its honesty, humor, and authentic portrayal of Black experiences, making her the perfect person to teach a class on creating content that breaks boundaries and resonates with diverse audiences.

Who Should Get Issa Rae MasterClass?

Issa Rae started her career as a small-time YouTube content creator and is now a household name. People wanting to thrive in the entertainment industry stand to learn a lot from her. 

Aspiring Creators of Color: Issa Rae’s journey from web series to starring in large production television series is a beacon of hope for aspiring creators who share similar backgrounds. Her class will offer valuable insights and inspiration for people who want to tell their stories that challenge stereotypes and celebrate cultural inclusivity and positivity.

Storytellers with a Mission: If you are passionate about crafting narratives that reflect the complexities of the real world and push the boundaries, then Issa Rae’s MasterClass is perfect for you. She will help you find your unique voice and use storytelling’s power to spark conversations and challenge deep-rooted industry prejudice.

Writers and Actors Seeking Inspiration: Whether your focus is on writing compelling scripts or bringing characters to life on screen, Issa Rae’s MasterClass will offer you a ton of knowledge. She explores the art of character development, scriptwriting techniques, and the collaborative production world.

Those Who Want to Build a Creative Community: MasterClass as a learning platform encourages a sense of camaraderie amongst aspiring creators. This allows you to have an opportunity to learn from and be inspired by people who share your passion.

Anyone Who Wants to Learn from a Self-Made Success Story: If you closely follow Issa Rae’s success story, you will know her life is an inspiring case study in hustle and determination. Her MasterClass will let you understand her journey and give you actionable advice on breaking into and standing out in a competitive industry.

What does Issa Rae MasterClass cover?

Issa Rae’s MasterClass is 2 hours and 17 minutes long and is divided into 14 lessons of around 10 minutes each. Rae uses a conversational approach while teaching this class, so the whole course feels like having a long chat with a friend.

However, this style of teaching might only be suitable for some. Due to the conversational format, the lessons sometimes feel unstructured, and you may feel a little distracted and confused. But if you like this style of teaching, then you will surely enjoy having Issa Rae as your instructor.

The best thing about Issa Rae’s MasterClass (apart from Issa Rae herself) is the workbook she provides with the lessons. It not only summarizes the video lessons but takes it one step further. The workbook also lists assignments you can do to get your money’s worth out of this MasterClass.

Issa Rae’s MasterClass lacks a strong community interaction. While the connection with Issa is crucial, the overall platform suffers from limited digital interaction and guidance for correspondence among learners.

The lesson plan is as follows:

  1. Meet Your Instructor: Issa Rae
  2. Finding Your Voice and Inspiration
  3. Developing Your Story
  4. Insecure Plot Blueprint: Characters and The Why
  5. Insecure Plot Blueprint: Conflict and Series Setup
  6. Creating Characters Grounded In Reality
  7. Constructing Multidimensional Characters: Insecure
  8. Interpreting Feedback and Evolving Your Story
  9. Getting Your Stories Out There
  10. Resourcefulness Is Everything
  11. Collaborating With Like-Minded Creatives
  12. Empowering Yourself and Those Around You
  13. Diversify Your Skills
  14. Pep Talk: You Ready to Do This?

Summarizing Issa Rae’s Video Lessons

You might know Issa Rae as President Barbie, but you must realize she tells authentic stories with realistic characters. In this class, you will meet the screenwriter side of Issa Rae. 

She talks about her journey into television and film. She was just a girl (like any of us) with big dreams of selling stories that reflected the girl she saw in the mirror. The lack of black representation in the mainstream media ate Issa alive.

Issa faced many closed doors when she traditionally pitched her ideas to producers. Finally, she self-produced her work and started her own YouTube series, “Awkward Black Girl.” The series was a success and was massively popular and appreciated.

Issa teaches you how to create what you want to see by getting inspiration from your favorite shows and bringing underrepresented stories to a larger audience. She discusses how we always present our best parts and hide the ugly parts at all costs. However, Rae explains that the ugly parts are the best parts when writing a story, as everybody has them, which will make your character more relatable.

Rae walks you through every story’s ingredients and explains how to test your stories with new audiences. She explains that the best stories will make you feel invested and have a strong narrator that you root for.

 Even in her comedies, you will always find elements of drama and tension. You may wonder why comedies need tension, but Issa explains that those elements make the most compelling stories for the audience.

In the following lesson, Issa discusses how to write an impactful pilot episode and walks you through her writing process using “Insecure” as a case study. While explaining the significance of the pilot episode, Issa mentions that it is the official access to your show. You are not just setting up your world; you are setting up your characters. It is the first episode of your series and the guidebook for the whole first season and the entire show.

Issa continues her breakdown of the Insecure pilot so you can learn how to construct conflict and set up the rest of your series. She gives tips on creating organic conflicts that resonate with the audience. Issa talks about the biggest misconception about writing conflicts: people assume it to be in one place or that it is leading up to the conflict you anticipate. She suggests that you need to be setting up these tensions all along.

The thing that makes or breaks any TV show is its characters. Issa shows you the best ways to develop relatable and realistic characters and dialogue in the following two lessons. Awkward Black Girl and Insecure have something essential in common: solid and specific characters. Issa delves into some of the most notable characters from her series and the growth they’ve experienced over time.

Issa will help you discover how to present your vision to others, get the most from critical feedback, and find the right partners for your project. Her journey proves that distribution can include something other than Hollywood executives and big budgets. Issa gives you tips on how to get your stories in front of an audience without a TV network.

Issa explains the significance of being resourceful when writing unique stories. She discusses how to mine your friends, family, and colleagues for a good story. Once you have your foundational story straight, Issa suggests ways to lean on the expertise of creatives around you, particularly in a writers’ room full of diverse voices and ideas.

Issa then shares personal stories of times when she had to trust her gut, feel confident in her voice, and help other creatives gain opportunities in the entertainment industry. As a Black woman, she understands the necessity of support in the entertainment industry and tries to do that for as many people as possible.

As one of the leading multi-hyphenates today, Issa doesn’t believe that it always makes sense to “stay in your lane.” she will help you discover why it is crucial to expand your skills. Issa ends her class with a motivational speech. We all need a pep talk once in a while. She reveals why a resilient mentality is a must to survive in a highly competitive industry.

Key Points from Issa Rae MasterClass:

As an incredibly impatient person, the most important thing I learned from Issa Rae’s MasterClass is how to be patient. Issa explains that success seems like it is coming overnight, but that is never the case. You need to work hard and wait for that work to get recognition. It might happen instantly, or it might take a while. You don’t need to worry as long as you have given it your best effort.

Issa suggests using your own life (and the people in it) as resource material for your writing. This would work if all of us had interesting lives, but that is not the reality. However, Issa gives tips on how you can incorporate your experiences and struggles in your work and make it engaging and relatable for your audiences, and that is something I will do in my work.

Besides mining your life for writing material, Issa advices you to constantly read more. As someone who does not enjoy reading, this felt like a challenge. Issa provided a list of reference material as additional resources in her guidebook, and I decided to try it. I was thoroughly surprised at how much I enjoyed reading her recommended books, and now I will be looking forward to reading more.

My most crucial takeaway from Issa Rae’s MasterClass is consistency. I lack discipline when it comes to writing. My notebooks are full of unfinished ideas and thoughts that I have stopped following through on, and Issa explains why doing that can be detrimental to your writing process. Issa helped me understand the importance of seeing your work through and deciding if it is good enough or not. Quitting is never the answer.

What did I Like about Issa Rae’s MasterClass?

Issa Rae’s MasterClass was full of revelations for me. I liked everything about it, but a few things stood out. They are:

From Web Series to MasterClass: Issa Rae’s MasterClass is not just about writing or acting; it teaches you how to hustle. You journey with her, from creating viral content to crafting critically acclaimed TV shows. I got to look at things from her perspective and gained valuable insights. Her story can help many aspiring creators as it demystifies the climb (from small bedroom projects to industrial success).

Developing Characters You Love (and Can’t Help But Root For): I have only ever seen people of color as quirky best friends or a character in the shadows. Issa Rae inspired me to change that. Her characters are flawed, funny, and fiercely honest. Her MasterClass dissects the art of developing characters that resonate with the audience. She taught me how to do the same. I also understood the importance of being culturally diverse in a respectable way.

Finding Your Voice and Telling Stories That Matter: In a world saturated with content, Issa Rae’s MasterClass encouraged me to find my unique voice and create stories that push boundaries. Her lessons will guide you through identifying what truly feels natural to you, helping you tell stories that are beyond entertaining; they are thought-provoking and challenge perspectives.

From Script to Screen: A Collaborative Mastermind Class: Writing a screenplay is simple enough, but bringing it to life is another ball game. Issa Rae’s MasterClass is about more than just writing the initial script. She offers actionable tips on collaborating, navigating production processes, and working effectively with actors, directors, and the whole creative team. She taught me the significance of respecting everyone’s opinions without compromising your work.

Building Your Creative Community: Anyone who has been in showbiz knows that the journey of a visionary creator can be lonely and challenging. Issa Rae’s MasterClass fosters a sense of community. I appreciated the chance to connect with other aspiring creators and share my experiences with them. This supportive environment was a powerful motivator for me as I navigated my creative path.

Issa Rae MasterClass Conclusion

So, did Issa Rae’s MasterClass turn me into an overnight Hollywood sensation?

Let’s be honest; the path from drama student to award-winning showrunner is probably paved with a few more rejections and late-night writing sessions than the MasterClass covered. But here’s the thing: this class was not about instant fame for me. It was about getting a peek behind the curtain from someone who looks like me and tells stories that resonate with the experiences I, and so many others, share.

Issa Rae’s MasterClass reignited a fire in my heart. It was no longer about the technical aspects of writing and acting; it was about the power of using these tools to create narratives that reflect the complexities of my world.

Issa’s emphasis on finding your voice and telling stories that matter – stories that challenge stereotypes and celebrate the beauty of underrepresented experiences – struck a deep chord within me.

Suddenly, the blank pages in my notebook and my partially finished stories stopped being so daunting. They were brimming with possibilities, waiting to be filled with characters and stories that needed to be seen and heard.

Beyond the technical knowledge, Issa Rae’s MasterClass fostered a sense of community. Connecting with other aspiring creators of color, swapping stories, and sharing a collective dream was an unexpected perk. There is a silent power in seeing yourself reflected in the journeys of others, a sense of “we can do this” that transcends the isolation sometimes inherent in the creative process.

So, is Issa Rae’s MasterClass worth it?

The answer to that would be a resounding YES.

If you’re a budding writer or actor, especially one yearning to tell stories that break boundaries and celebrate people of color, then this MasterClass is a Godsent. It is not a magic bullet to success but a potent blend of inspiration, practical guidance, and a supportive community that can propel you forward on your creative journey.

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