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Tag: Issa Rae

  • Issa Rae & Prentice Penny Launch ‘Insecure’ Podcast

    Remember the days of “appointment television”? For many, HBO’s “Insecure” was exactly that. Even though the groundbreaking series wrapped up in 2021, its cultural impact is still felt. Now, co-creator and star Issa Rae and showrunner Prentice Penny are taking us behind the scenes with a brand-new podcast, diving deep into the stories that made “Insecure” so special.

    Introducing ‘Blocc Party: An Insecure Podcast’

    Launched by Issa’s Hoo Rae Productions, “Blocc Party: An Insecure Podcast” promises to relive the magic of the show. Issa and Prentice are joined by former cast members, writers, and other key players to unpack everything from the early days to the emotional final moments. It’s a chance to hear the untold stories and gain new insights into the beloved series.

    Reflecting on the final day of filming, Issa didn’t hold back about the emotional toll. “It was ending the show itself, like stopping filming, was devastating but also a relief,” she shared with Prentice. She described the experience as incredibly emotional, admitting, “I don’t know that I’ve ever cried so much in my life.” It’s clear that “Insecure” was more than just a job; it was a significant chapter for everyone involved.

    The Legacy of ‘Insecure’ on HBO

    When “Insecure” premiered in 2016, it marked a significant moment for representation on HBO. It was one of the few shows led by Black women in leading roles on the network in recent memory. The last comparable series, “The No. 1 Ladies Detective Agency,” starring Jill Scott and Anika Noni Rose, had a much shorter run.

    Issa and Prentice recognized the demand for authentic storytelling. Prentice recalled the era, noting, “It was the Obama years of like wanting like hey where are all the black people?” They aimed to fill that void, especially after the 2008 TV writer’s strike impacted several shows featuring Black casts, like “Girlfriends.”

    More from Issa Rae

    While fans are eagerly diving into the “Insecure” podcast, Issa Rae has been busy making waves elsewhere. Her microseries “Screen Time,” launched on TikTok and Prime Video, has already garnered nearly 75 million views since its debut on April 29th. The first 27 episodes are available, with more on the way.

    It’s clear that Issa Rae continues to be a powerhouse in the entertainment industry, creating content that resonates deeply with audiences and sparks important conversations. The “Insecure” podcast is just the latest testament to her incredible storytelling ability.

    Have you listened to ‘Blocc Party: An Insecure Podcast’ yet? What are your favorite memories from ‘Insecure’? Let us know in the comments!

  • Issa Rae’s Guiding Principle from Maya Angelou

    What’s the secret to navigating the complexities of both business and life? For acclaimed creator Issa Rae, the answer comes from a timeless piece of wisdom shared by the legendary Maya Angelou. It’s a lesson that centers on trusting your instincts and protecting your peace.

    The Power of First Impressions

    During a panel at the Create Canva/Building Creative Empires for Social Good event in Los Angeles on April 16, Rae revealed the quote that has profoundly influenced her. “My girl Maya says when someone shows you who they are, believe them the first time,” Rae shared with the audience. This powerful advice, widely attributed to Angelou, encourages us to recognize people’s true character from the outset, without second-guessing.

    Rae admitted that she hasn’t always adhered to this guidance, particularly in her professional life. She confessed to sometimes giving people the benefit of the doubt, even when her gut feeling signaled otherwise. “Sometimes I’ve had situations where I tried to give someone the benefit of the doubt,” she said, acknowledging that her instincts often raised red flags that she chose to ignore.

    Angelou’s Enduring Influence

    Maya Angelou, who passed away in 2014 at the age of 86, continues to inspire generations with her profound writings on identity, resilience, and personal truth. Her wisdom clearly resonates deeply with Rae, shaping her decisions both creatively and personally.

    Rae also reflected on her career, highlighting her HBO series “Insecure” (2016-2021) as a major achievement. She emphasized its role in paving the way for other Black writers, creators, and producers in the entertainment industry. Beyond television, Rae has expanded her influence by producing studio films, aiming to bring more diverse stories to mainstream audiences.

    Integrating Values and Ambition

    Rae’s journey exemplifies how personal values, guided by influential figures like Maya Angelou, can intersect with creative ambition. The lesson to trust your instincts serves as a powerful reminder to stay true to yourself and protect your energy, whether you’re building a creative empire or simply navigating daily life.

    How do you apply Maya Angelou’s lesson in your own life? Do you trust your first impressions? Share your experiences in the comments below!

  • Issa Rae’s New TikTok Microdrama ‘Screen Time’

    Get ready for your next binge-watch, but make it short! Issa Rae, the creative force behind “Insecure,” is diving back into the world of digital storytelling with a brand-new microdrama series on TikTok. Her production company, Hoorae Media, is teaming up with the popular platform for a project titled “Screen Time,” designed specifically for today’s mobile-first audience.

    A Return to Digital Roots

    This collaboration marks a significant move for Hoorae Media, embracing the fast-paced, short-form content that dominates online viewing habits. Rae herself spoke about this strategic shift at TheWrap’s Creators x Hollywood Summit, emphasizing the importance of staying relevant in an evolving media landscape. “Screen Time” is set to debut later this month, promising quick, engaging installments.

    The series is described as a microdrama, meaning each episode will be short and impactful. The plot centers around a seemingly normal movie night date that takes a dramatic turn when an unexpected interruption forces the characters to confront hidden secrets. Expect suspense and relationship drama packed into bite-sized episodes perfect for scrolling.

    TikTok’s Growing Investment in Serialized Content

    This partnership goes beyond just one series. TikTok and Hoorae Media plan to co-develop more micro-series, which will be exclusively released on TikTok and its dedicated microdrama platform, PineDrama. This initiative highlights TikTok’s increasing focus on serialized storytelling as it competes with traditional and streaming services.

    For Issa Rae, this venture is a full-circle moment. She first gained national recognition with her groundbreaking YouTube series, “The Mis-Adventures of Awkward Black Girl.” That digital success paved the way for her mainstream career, including the critically acclaimed HBO series “Insecure.” Now, she’s returning to the platform that helped launch her career.

    Meet the Cast

    The “Screen Time” cast includes Brittney Jefferson, Eric C. Lynch, Jasmine Luv, Xavier Avila, and Jenna Nolen. This ensemble brings together talent from both the digital content creation world and more established entertainment backgrounds, promising a dynamic viewing experience.

    Are you excited to watch Issa Rae’s new microdrama series ‘Screen Time’ on TikTok? What do you think about this trend of short-form content? Share your thoughts in the comments below!

  • Issa Rae Honors Brandy at Walk of Fame Ceremony

    The iconic Brandy officially received her star on the Hollywood Walk of Fame on March 30, 2026, and the celebration was filled with heartfelt tributes. Among the notable speakers was none other than television mogul Issa Rae, who didn’t hold back in expressing her admiration for the R&B superstar.

    Issa Rae: Brandy is ‘The Blueprint’

    Issa Rae, the creative force behind “Insecure,” spoke passionately about Brandy’s profound influence on her life and career. Rae described Brandy as “the blueprint,” emphasizing how instrumental the beloved 90s sitcom “Moesha” was in shaping her own aspirations as a writer and creator.

    “It was really ‘Moesha’ that made me understand what was possible,” Rae shared during her remarks. She highlighted how “Moesha” was the first show she saw that truly represented an “ordinary Black girl’s point of view.” At a time when television beauty standards didn’t reflect many young Black women, Brandy, as Moesha, set a new standard of effortless cool and unapologetic beauty.

    The Lasting Impact of ‘Moesha’

    Rae went on to explain that Brandy’s career trajectory, constantly evolving and expanding beyond a single lane, was particularly inspirational. “To me, Brandy was and is the blueprint,” Rae stated emphatically. “Without Brandy as ‘Moesha,’ there’s no ‘The Parkers,’ there’s no ‘Girlfriends.’ There’s no ‘Insecure,’ and honestly, without ‘Moesha’ there’s no me as a writer.”

    The impact of “Moesha,” which ran for six seasons on UPN, extended far beyond its own narrative. It spawned successful spin-offs like “The Parkers” and existed within the same universe as “Girlfriends” and “The Game,” creating a significant television footprint.

    Brandy’s Own Words on Legacy

    Brandy herself, alongside other guests including Kenneth “Babyface” Edmonds and Kehlani, spoke about the significance of the honor. “A star on the Walk of Fame is a definition of legacy,” Brandy reflected. She emphasized that it celebrates endurance, artistic impact, and the realization of dreams, stating, “Dreams don’t have an expiration date.”

    The ceremony was attended by many who have been touched by Brandy’s career, including the cast of “Moesha,” her daughter Sy’rai, and her “The Boy Is Mine” duet partner Monica. It was a powerful testament to Brandy’s enduring influence on music, television, and culture.

    What are your favorite Brandy moments or songs? Share them in the comments below!

  • Issa Rae Admits Feeling ‘Stagnant’ in Her Career

    Even cultural icons like Issa Rae experience moments of self-doubt. The brilliant writer, producer, and actress recently shared on a podcast that she often feels a sense of career ‘stagnation,’ especially when her projects aren’t actively airing.

    The Pressure of Constant Success

    In a candid conversation on the debut episode of the “Not My Best Moment” podcast with host KevOnStage (Kevin Fredericks), Rae, 40, admitted that despite her outward success, she struggles internally. “I know that I appear successful to other people, but right now, no, I feel really stagnant,” she revealed.

    She elaborated that this feeling is quite literal: her sense of accomplishment is directly tied to when her work is visible. “I only really feel a sense of success when my sh— is on the air,” Rae explained. This connection to her television work, particularly her groundbreaking HBO series “Insecure,” seems to be a core part of her professional identity.

    Beyond the Screen: A Creative Empire

    Rae has certainly built an expansive creative empire since “Insecure” concluded. She’s starred in hit films, produced critically acclaimed projects across various genres, released books, and launched multiple businesses. Yet, she confessed that these ventures, while fulfilling passion projects, don’t ignite the same excitement as seeing her TV shows on air.

    When Fredericks playfully asked if she feels like ‘nothing’ once a project wraps, Rae laughed and confirmed the sentiment. “Yeah,” she said. “I haven’t put words to it but that’s exactly how it feels. I am nothing again is crazy … it’s so real.”

    Reflections on Impulsivity and Growth

    This admission comes on the heels of Rae’s latest essay collection, “I Should Be Smarter Now.” In it, she delves into the challenges and lessons learned throughout her career, including a significant mistake driven by her ‘impulsivity.’ She describes this trait as both a gift and a curse, enabling her to be fearless in pursuing her goals but also leading to costly errors.

    Do you ever feel stagnant in your own career, even when you’re busy? Share your experiences and thoughts in the comments below!

  • Malcolm-Jamal Warner on Theo Huxtable Role

    The recent passing of Malcolm-Jamal Warner left a void in the hearts of many, particularly within Black communities. In one of his final on-screen appearances, featured in Issa Rae’s documentary “Seen & Heard: The History of Black Television,” Warner shared poignant reflections on his iconic role as Theo Huxtable on “The Cosby Show.” This role not only defined a significant part of his career but also made him feel like a familiar presence in households across the nation.

    Auditioning for a Cultural Touchstone

    Warner, who was just 13 when he auditioned for the part, recalled being influenced by the smart-aleck characters he saw on shows like “Diff’rent Strokes.” He felt he nailed his audition for “The Cosby Show,” earning smiles from most of the room. However, he specifically remembers Bill Cosby’s reaction.

    Cosby, the show’s creator, looked at the young actor and asked, “Would you really talk to your father like that?” Upon Warner’s negative response, Cosby stated, “I don’t want to see that on this show.” This interaction highlights Cosby’s vision for the Huxtable family dynamic, aiming for a portrayal that emphasized respect and positive family interactions.

    Navigating ‘The Cosby Show’s’ Vision

    Despite the show’s current controversial associations with Bill Cosby, “The Cosby Show” was undeniably a groundbreaking series. It presented a level of Black storytelling that was largely unexplored in Hollywood at the time. Warner noted that Cosby was fiercely protective of his vision for the show, constantly reminding network producers, writers, and the studio of the specific narrative they were creating.

    Warner witnessed this dedication firsthand, stating, “I watched him do that from year one to year eight. That battle never, never stopped, until the show stopped.” This constant vigilance ensured the show maintained its unique identity and message throughout its successful run.

    The Lasting Impact of the Huxtable Family

    Malcolm-Jamal Warner, who tragically passed away on July 20, 2025, at the age of 54, continued to work on various projects after “The Cosby Show.” Yet, he remained acutely aware of the profound impact the Huxtable family had on Black viewers. He shared in the documentary how he received tens of thousands of letters from people who identified with the family, saying, “We are the Huxtables.”

    Even though the show faced criticism for not always reflecting the entirety of the Black experience, its representation of a successful, loving Black family resonated deeply. Warner’s reflections in “Seen & Heard” offer a valuable look back at a pivotal moment in television history and the enduring legacy of his beloved character.

    Fans can catch Malcolm-Jamal Warner’s final on-screen appearance in the upcoming premiere of Fox’s crime drama “Murder in a Small Town” on October 7. Both parts of “Seen & Heard: The History of Black Television” are available to stream on HBO Max.

    What are your favorite memories of Theo Huxtable or “The Cosby Show”? Share your thoughts in the comments below!

  • Issa Rae: New Book, Beauty, and Boss Mode

    Issa Rae is a name synonymous with groundbreaking success, from her early days on YouTube with ‘Awkward Black Girl’ to the critically acclaimed HBO series ‘Insecure.’ She’s not just a force in television and film but also a champion for underrepresented creators and a co-founder of the beauty brand Sienna Naturals. Now, she’s offering a more intimate glimpse into her world with her new book, ‘I Should Be Smarter By Now.’

    A Deep Dive into ‘I Should Be Smarter By Now’

    This collection of six essays feels like a heartfelt conversation with a friend. Issa dives into her journey from adolescence to navigating her 30s and 40s, embracing the messy, relatable contradictions that come with growth. It’s a guide for anyone who’s ever felt uncertain while chasing a dream or evolving into their next self.

    The title itself, ‘I Should Be Smarter By Now,’ stems from a place of reflection on past experiences and mistakes. Issa wanted to offer an approachable, self-deprecating look at pursuing a dream, making it clear that growth isn’t always a straight line. This new collection serves as an update to her earlier work, showing where she is now with a clearer understanding of herself.

    Embracing Honesty and Transparency

    As a leader and creator, Issa has intentionally added new tools to her professional ‘toolbox.’ One of the most significant is her increased ability to be honest and transparent, even when it means delivering hard truths. She’s shedding the people-pleasing tendencies, realizing that directness, delivered gently, saves time and fosters respect.

    This approach allows for more authentic interactions, both personally and professionally. It’s a delicate balance she’s still honing, but the commitment to clarity is a powerful step in building lasting relationships and projects.

    Water as a Source of Reset and Recharge

    Issa’s essay ‘The Art of Strategic Procrastination’ touches on creative work done by the ocean. This connection to water extends beyond creative retreats; it’s a core part of her self-care. She finds peace and relaxation listening to ocean sounds or rain at night and has embraced baths as a significant part of her routine over the last five years.

    Having a pool at home was essential for her, providing a space to swim, rest, and recharge whenever needed. Water, for Issa, is undeniably her happy place, a vital element for resetting her mind and body.

    Hairstyles That Mean Business

    When it comes to making a statement, Issa has a go-to style choice: a high bun or high ponytail. She describes these taut styles as her ‘work uniform,’ signaling that she’s in ‘work mode’ and ready to focus. The lack of hair in her face allows her to channel her energy into getting things done.

    She also finds power in wearing rings, especially since she speaks with her hands. These small details, combined with a fresh manicure, create a sense of readiness and confidence. It’s a reminder that personal style can be a powerful tool for stepping into your professional power.

    Sienna Naturals: Healthy Hair on the Horizon

    As co-founder of Sienna Naturals, Issa is dedicated to promoting healthy hair and scalp care. The brand recently launched its first styling product, the Dream Curl Gelée. This innovative gelée offers excellent hold for defining curls and textured hair without the dreaded crunch, while also hydrating strands.

    It’s designed to work for various styles, from wash-and-gos to braid-outs, ensuring that textured hair can be styled and maintained with health and hydration at the forefront. This launch is a testament to Sienna Naturals’ commitment to providing effective, nourishing solutions for curly and textured hair.

    Simple Pleasures: The Joy of Running

    Beyond her creative and professional endeavors, Issa finds joy in a simple pleasure: running. It’s become her happy place, a way to explore new places while traveling and to get out of her own head. Listening to music, often curated playlists of new releases, enhances her runs and serves as her dedicated time for discovering new tunes.

    What are your thoughts on Issa Rae’s new book and her approach to beauty and self-care? Do you have a go-to hairstyle that makes you feel ready to take on the world? Share your insights in the comments below!

  • Issa Rae: Impulsivity is a Gift and Curse

    Issa Rae, the acclaimed creator behind “Insecure,” is known for her sharp wit and candid storytelling. In her newly released essay collection, “I Should Be Smarter by Now,” Rae delves into the highs and lows of her journey, particularly highlighting how her own impulsivity has been both a driving force for success and a source of significant financial risk.

    The Double-Edged Sword of Impulsivity

    Rae describes her impulsivity as a trait that has “benefited from and paid dearly for.” She explains that while it fuels her fearlessness in pursuing her goals – allowing her to be proactive and go after what she wants – it also leads to a lack of foresight regarding the consequences of her actions. Unlike creatives who might overthink, Rae identifies as an “underthinker.”

    This tendency to act quickly without fully considering the financial implications nearly led her to bankruptcy. Rae recounts a pivotal moment in 2014 when, despite having saved money from her writing career and receiving a substantial advance for her memoir, “The Misadventures of Awkward Black Girl,” a series of impulsive decisions put her finances in jeopardy.

    Financial Missteps and Near Bankruptcy

    While working on an independent comedy pilot, Rae received a call from her business manager warning that “every penny you’ve saved is about to be gone.” She cites three major mistakes that contributed to this near-financial collapse. The first involved launching her independent production company, ColorCreative, with her partner Deniese Davis. Before securing investor funding, they had already established a schedule, solicited scripts, and met with writers, despite not getting many investment “bites.”

    Rae’s second mistake was reaching out to an “ex” for funding. The third, and perhaps most critical, was getting into an argument with this same ex just a week before their scheduled shoot. Rae admits the real error was not halting the project when she knew she lacked the necessary funds, which ultimately meant the costs would fall entirely on her. At the time, she was short $150,000, with most of her savings coming from her book advance and personal savings – essentially, all the money she had ever made.

    Lessons Learned from Financial Risks

    Rae’s candid reflection in “I Should Be Smarter by Now” offers valuable insights into the challenges faced by creatives and entrepreneurs, especially when navigating the early stages of building a business. Her story serves as a reminder of the importance of financial planning and the potential pitfalls of unchecked impulsivity, even when driven by passion and vision.

    What are your thoughts on Issa Rae’s experience with impulsivity and financial risk? Have you faced similar challenges in your own career or business ventures? Share your stories in the comments below!

  • Issa Rae’s Near Financial Disaster Revealed in New Book

    Issa Rae, the acclaimed writer and producer behind “Insecure,” is sharing some of her most valuable career lessons in her new essay collection, “I Should Be Smarter By Now.” Released in partnership with Amazon and Audible, the book offers a candid look at her journey, including a risky early career move that almost cost her everything.

    Impulsivity: A Gift and a Curse

    Rae describes her impulsivity as both a blessing and a curse. While it fuels her fearlessness in pursuing her goals, it also means she sometimes doesn’t fully consider the consequences. This trait, combined with being a self-described “underthinker,” led to a significant learning experience early in her career.

    In 2014, when Rae and her ColorCreative partner Deniese Davis launched their company, they ambitiously decided to produce three TV pilots without secured funding. Rae recalled reaching out to an ex who initially promised to invest a portion of the needed capital, but a subsequent argument left them without the funds.

    The Near-Miss Financial Gamble

    The real mistake, Rae admits, was not stopping the project when she realized the money wasn’t there and the financial burden would fall solely on her. She needed $150,000 and only had about half of that, primarily from her advance for her first book, “Adventures of an Awkward Black Girl.” “Most of it was in my savings — it was all the money I had ever made in my life up until that point,” she revealed.

    Despite the precarious financial situation, Rae and Davis pushed forward, shooting all three pilots with Rae as the primary financial backer. Although these pilots didn’t immediately find a home, the gamble proved foundational for ColorCreative’s growth and helped Rae hone her business acumen.

    Essays on Creativity and Resilience

    Beyond this dramatic story, Rae’s collection delves into creativity, collaboration, and resilience. Essays like “The Business of Being Me” and “The Art of Strategic Procrastination” offer raw, honest insights into the often messy path to success. Rae describes the book as a mix of confession, reflection, and sharing what she wishes she knew earlier.

    To celebrate the release, Rae is embarking on a six-city book tour, starting September 8th in Philadelphia, with stops in Atlanta, Washington D.C., Dallas, Chicago, and Detroit. She hopes these stories will resonate with anyone building something, big or small.

    Have you ever taken a big risk in your career? Share your experiences in the comments below!

  • Issa Rae, Steve Harvey & More Share Success Secrets at InvestFest

    InvestFest 2025 recently brought together a powerhouse lineup of moguls, CEOs, and influencers, all eager to share their hard-earned wisdom on success, leadership, and building a lasting legacy. This annual festival, founded by Earn Your Leisure (EYL), transformed the Georgia World Congress Center into a hub for entrepreneurship, financial literacy, and pop culture, drawing thousands of attendees.

    Masters of Their Craft Share Insights

    The festival featured a dynamic weekend of panels, live interviews, and networking opportunities. EYL founders Rashad Bilal and Troy Millings described the event as the culmination of a year-long planning process, meticulously focused on delivering essential knowledge to the community. Topics ranged from AI and real estate to cryptocurrency, ensuring attendees received concentrated, valuable information.

    Beyond the main panels, InvestFest also boasted a vibrant marketplace showcasing over 400 businesses. Game-changing additions included a Deal Room and a live Open Pitch competition with a substantial $125,000 prize. Headlining speakers like Issa Rae, Steve Harvey, Charlamagne Tha God, and Magic Johnson provided masterclasses in wealth creation and self-empowerment.

    Key Takeaways from the Moguls

    Steve Harvey delivered a powerful message of self-belief, calling attendees the “chosen ones” for investing in themselves. He stressed the importance of authenticity, urging everyone to embrace their unique life stories. “God picked you a long time ago, that’s why you’re the first one in your family,” Harvey shared, highlighting the significance of their journey.

    Basketball legend and business mogul Magic Johnson shared a pivotal lesson from his youth: choosing a lump sum of cash over Nike stock. He revealed that the stock would be worth over a billion dollars today, a humbling realization that fuels his mission to educate others about financial literacy. Johnson also emphasized his relentless drive, waking at 4 AM and working tirelessly, driven by self-motivation.

    Both Harvey and Johnson underscored the importance of using personal success to uplift the community. Harvey stated, “We can make each other great,” and advised attendees to identify their God-given gifts, emphasizing that true power lies in ownership. “I would rather own ABC, than be on ABC,” he asserted.

    Charlamagne Tha God echoed these sentiments, reminding attendees of the power of authenticity. “Your journey, who you are, God put you in that unique situation for a reason,” he said. “So don’t be afraid to tell that story, that’s how you become a very authentic personality.”

    Issa Rae offered unique insights into her business acumen, advocating for “networking across” rather than “networking up.” She encourages building strong connections with peers at a similar stage in their careers, a strategy that has fueled her immense success as the creator of “Insecure.” “Every piece has been connected to someone else, and I’m not being foolish enough to think I can do every single one on my own,” Rae shared.

    The event also saw notable appearances from hosts Paige Shari, Anisa Brenee, and Miss Basketball, as well as figures like realtor Quiana Watson, Derrick Hayes and Pinky Cole, and Fawn Weaver and Tabitha Brown, all contributing to the vibrant atmosphere.

    What was your biggest takeaway from the success secrets shared at InvestFest 2025? Let us know in the comments below!