When I Was Your Age Summary and Analysis
When I Was Your Age by Kenan Thompson is a candid, humorous, and deeply personal memoir that blends reflections on fame, fatherhood, and growing up as a Black man in America.
Known for his long-running role on Saturday Night Live and his early Nickelodeon fame, Thompson steps away from the spotlight’s caricatures to share his real self. Through a series of essays, he recounts pivotal moments—from childhood to stardom, from heartbreak to healing—with honesty and charm.
This isn’t just a celebrity tell-all; it’s a coming-of-age story that spans decades and highlights the human side of a comedy legend, shaped by joy, failure, resilience, and love.
Summary
Kenan Thompson begins his story by acknowledging the gap between the public perception of his life and the reality.
While many know him as a constant on-screen presence, few know his path behind the scenes—the struggles, values, and moments that shaped him.
He sets the tone with the promise of sharing real stories, especially as a father raising daughters in a different world than he grew up in.
Kenan’s journey starts with his teenage breakthrough on All That, where he found early fame and forged lifelong friendships with castmates like Kel Mitchell.
Being on set at Universal Studios was both exciting and overwhelming.
Beneath the laughter and chaos of teen stardom, Kenan navigated self-doubt and the pressure to perform, even as he quickly became a beloved figure among his peers.
He then moves backward to childhood in Atlanta, a city filled with cultural pride but marked by quiet segregation.
His upbringing in a tight-knit Black community instilled in him strength and moral grounding.
His father, cautious and protective, shaped Kenan’s early understanding of race in America.
His bond with his older brother Kerwin and memories of independence as a latchkey kid laid the foundation for his humor and introspection.
Church played a central role in Kenan’s life, not just spiritually but socially.
Weekly services, gospel choirs, and Black church culture provided discipline, inspiration, and stage time.
While his adult life veered away from organized religion, he still holds on to the lessons and values it instilled.
Parenthood redefined Kenan.
He humorously admits that becoming a dad made him “uncool,” but it also brought deeper clarity.
His daughters, Georgia and Gianna, are central to his identity now.
He learns from them daily and recognizes that being a good father means evolving constantly.
Television shaped his ambitions.
As a child, he watched classic Black-led sitcoms and memorized lines, developing comedic instincts that would serve him later.
He admired figures like Eddie Murphy and Bill Cosby, seeing them as examples of excellence.
This love of TV turned into mimicry and performance, eventually paving his way into acting.
Kenan’s path wasn’t without hardship.
He discusses his early years as a child actor—auditions, rejections, and the struggles of being a chubby Black boy in an industry obsessed with a narrow aesthetic.
His mother’s unwavering support kept him afloat.
He avoided the common downfalls of child stars by staying grounded.
Later, he faced real-world setbacks, including financial ruin.
Duped by a corrupt accountant, Kenan lost much of his early earnings.
This painful chapter forced him to reassess his priorities and develop financial literacy.
He’s grateful for the wake-up call, believing it made him more responsible.
He touches on perseverance—how to tell when to keep pushing or step back.
While doubt crept in during dry spells, he stayed focused thanks to mentors and gut instinct.
Even as fame grew, he longed for personal validation, especially from loved ones and his daughters.
Post-divorce, Kenan reentered the dating world cautiously.
While enjoying newfound independence, he’s reflective about the loneliness and change that come with it.
Encounters with celebrities—both inspiring and disappointing—taught him not to idealize anyone.
He believes in partnerships.
Whether it’s Kel Mitchell or his SNL writers, collaboration fueled his creativity.
Above all, it’s his daughters who offer the deepest lessons—on honesty, patience, and love.
The epilogue leaves readers with a sense of grounded optimism.
Kenan knows life changes constantly, but he’s committed to purpose, growth, and uplifting others.
He signs off with the wisdom of someone who’s been in the game for decades and still finds joy in being a father, artist, and teacher.
Key Characters
Kenan Thompson
Kenan is the central figure of the memoir, and his character evolves significantly across the chapters. He begins as a young, ambitious child actor thrust into the spotlight with All That, navigating fame with a mixture of nerves and resilience.
Early on, his persona is marked by youthful excitement and awe, but this gradually matures into introspection and wisdom. As he transitions into adulthood, Kenan reveals a strong moral compass shaped by his upbringing in Atlanta’s tight-knit Black community, the influence of the Black church, and his mother’s sacrifices.
His reflections on fatherhood show a transformation into a deeply involved, humble parent, who freely admits his insecurities and mistakes. Kenan’s ability to be self-deprecating while still maintaining pride in his identity makes him an incredibly relatable figure.
He carries a unique duality—publicly perceived as the “huggable cutie,” but privately burdened with the complexity of being a Black entertainer in predominantly white spaces. His desire to inspire, provide, and grow is grounded in authenticity and emotional intelligence.
Georgia and Gianna (Kenan’s Daughters)
Kenan’s daughters, Georgia and Gianna, serve as both muses and mirrors. Georgia is depicted as articulate and creative, the kind of child who engages in expressive thought and challenges her dad to think more deeply.
Gianna, on the other hand, is fierce and playful—a force of energy and mischief. Together, they not only anchor Kenan in his personal life but also reshape his worldview.
Through them, Kenan learns the value of presence, patience, and playful honesty. The girls represent the future Kenan is trying to build—a world that is kinder, wiser, and more inclusive.
Their roles extend beyond simply being children; they are key agents of Kenan’s personal development and the embodiment of his most important life lessons.
Kenan’s Mother
Kenan’s mother emerges as one of the strongest influences in his life. Her dedication is monumental—working multiple jobs to support his acting dreams and providing emotional and logistical support even when times were tough.
She is portrayed as pragmatic, protective, and nurturing, offering Kenan not only opportunities but also a moral foundation. Her sacrifices reflect the often-unseen labor behind a child star’s rise and serve as a recurring touchstone for Kenan’s gratitude and humility.
She is never overly romanticized but appreciated for her relentless drive, strategic decisions, and grounding influence.
Kel Mitchell and Josh Server (The “Three Amigos”)
Kel and Josh are more than colleagues—they are central to Kenan’s early career identity and social belonging. Their friendship forms during the All That years, where they bond over youthful hijinks and shared aspirations.
Kel, in particular, is a creative partner with whom Kenan forms one of the most iconic comedy duos in Nickelodeon history. These friendships provide Kenan with the emotional support needed to survive the pressures of child stardom.
The camaraderie, trust, and shared sense of mischief define this period of Kenan’s life and lay the groundwork for his later appreciation of collaboration and loyalty.
Kenan’s Older Brother (Kerwin)
Kerwin, though less prominent, is a symbolic figure in Kenan’s development. He represents a mix of protector, playmate, and occasional rival.
Their bond as latchkey kids strengthens Kenan’s independence and sense of humor. Kerwin is instrumental in those early improvisational moments, acting out TV characters and serving as an early audience for Kenan’s growing comedic instincts.
Their dynamic encapsulates brotherly affection rooted in shared experience and cultural heritage.
Mr. Beretta (The Shady Accountant)
Mr. Beretta stands in stark contrast to the supportive figures in Kenan’s life. Initially appearing as a trustworthy advisor, he later becomes a cautionary tale of misplaced trust.
This character represents the dark side of early success—where vulnerability and financial naivety can lead to betrayal. The betrayal by Mr. Beretta is a pivotal moment in Kenan’s adult arc, fueling his financial literacy journey and his renewed grounding in self-reliance.
He is emblematic of the lessons one learns not through textbooks, but through painful life experience.
Famous Figures and Industry Mentors
Scattered throughout the memoir are encounters with well-known figures—some encouraging, others disappointing. These interactions help shape Kenan’s understanding of fame and humanity.
While he never names all these individuals in exhaustive detail, he distinguishes between true mentorship and superficial celebrity. These figures act as both aspirational benchmarks and reality checks.
His admiration for figures like Eddie Murphy and Bill Cosby—each influential in distinct ways—offers insight into the shaping of Kenan’s comedic ethos. These reflections also invite complex discussions around morality and artistry.
The “Partner in Crime” Archetype
Kenan discusses the importance of having a “partner in crime” in various contexts—whether it’s in comedy with Kel, in marriage, or with trusted collaborators on SNL. This archetype speaks to his belief in synergy, the power of shared vision, and the need for mutual support in creative and personal endeavors.
It isn’t a single person but a recurring motif that emphasizes companionship and trust as cornerstones of his growth.
Themes
Identity and Representation
When I Was Your Age is the exploration of identity and representation—both as a personal journey and as a larger commentary on Black visibility in media. Kenan Thompson, as a successful Black entertainer who grew up in the racially charged atmosphere of Atlanta and later entered predominantly white spaces like Saturday Night Live, offers a compelling perspective on how identity is shaped, perceived, and at times, commodified.
Throughout the memoir, Kenan details how his childhood innocence about race gradually evolved into a deeper awareness of systemic barriers, especially in the entertainment industry. He is candid about the subtle and overt forms of typecasting, tokenism, and the pressures of being “the only one” in many professional rooms.
These experiences did not just shape his worldview but also informed how he carried himself on- and off-screen. Kenan’s reflections are not just confined to his own journey; they gesture toward broader conversations about cultural authenticity and the need for diverse voices.
He champions Black excellence not only through his own resilience and integrity but by acknowledging the collective struggle of his peers, ancestors, and community. Whether he’s talking about the pride he felt representing Black joy on All That, or the complexities of maintaining that joy at SNL, Kenan’s narrative highlights how representation isn’t merely about being seen—it’s about being respected, heard, and valued.
His life story becomes a powerful testament to the importance of holding onto one’s identity, even when surrounded by forces that might try to dilute or distort it.
Fatherhood and Family
Fatherhood serves as both a grounding force and a transformational experience in Kenan Thompson’s life. This theme is central to the memoir, shaping not only his decisions but also the very tone of the book, which oscillates between humor and heartfelt sincerity.
Kenan makes it abundantly clear that becoming a father fundamentally altered his priorities and outlook on life. He describes himself as having shifted from a performer focused on external validation to a parent deeply invested in creating a stable, loving, and morally sound environment for his daughters.
The sections where he reflects on his children—Georgia and Gianna—are marked by vulnerability, awe, and a deep sense of responsibility. Importantly, fatherhood is not portrayed in simplistic or overly sentimental terms.
Kenan is open about the challenges: feeling uncool, navigating single parenting after divorce, and the constant worry of whether he’s doing enough or doing things right. Yet, within those trials, he discovers profound truths about life, love, and what really matters.
His daughters don’t just receive his wisdom—they challenge it, expand it, and in many cases, redefine it. Through their questions, behaviors, and candid observations, they act as mirrors to Kenan’s strengths and flaws alike.
This dynamic turns fatherhood into a dialogue rather than a role, a mutual journey rather than a one-way transmission of values. Family, more broadly, also plays a critical role in shaping Kenan’s character.
From his mother’s tireless support during his acting days to his brother’s companionship, familial love provides the foundation upon which his career and ethics are built. Ultimately, Kenan’s depiction of fatherhood and family underscores that personal success is hollow without meaningful relationships and that true legacy lies in the values passed on to the next generation.
Career Perseverance and Resilience
Perseverance is perhaps the most recurrent and deeply personal theme of Kenan’s memoir. His professional journey—from childhood theater performances to becoming the longest-tenured cast member on Saturday Night Live—is filled with hurdles, near-misses, and critical self-evaluations.
He doesn’t glamorize the path to success but instead lays bare the grueling nature of sustaining a career in entertainment. Whether it was dealing with early rejections due to his non-traditional appearance, financial betrayal at the hands of a trusted accountant, or navigating a creative identity in an industry that often boxes in Black performers, Kenan’s story is one of continuous reinvention and steadfast belief in his craft.
What makes this theme particularly impactful is Kenan’s nuanced understanding of the difference between perseverance and delusion. He recounts moments where the line between the two blurred—where holding on felt less like bravery and more like self-sabotage.
Yet, through introspection and guidance from mentors, he learned to recalibrate, to pivot without abandoning his passion. This makes his resilience not just admirable but instructive.
It’s not about blind persistence; it’s about intelligent adaptability, humility, and the courage to start over when necessary. Kenan’s perseverance is also tied to a deeper mission: to honor those who came before him and open doors for those who will follow.
He approaches his longevity not as a personal victory but as a communal responsibility. By sharing both the wins and the wounds, Kenan offers readers a blueprint for resilience that is not rooted in toxic hustle culture but in self-awareness, purpose, and the will to keep showing up.
Humor and Emotional Intelligence
At the core of Kenan Thompson’s persona—and memoir—is humor, not just as a professional tool but as a survival mechanism and a form of emotional intelligence. His comedic voice, honed through years on sketch shows and sitcoms, is present throughout the book.
But what becomes clear as the chapters progress is that Kenan’s humor is layered. It’s not just about punchlines or impressions; it’s a way of processing the world, navigating discomfort, and connecting with people.
In recounting both his triumphs and tribulations, he uses wit to soften blows and make difficult truths more palatable—without ever diluting their significance. Emotional intelligence emerges as the quiet undercurrent of this theme.
Kenan is consistently reflective about how his actions and image affect others. For instance, his exploration of his “huggable cutie” persona reveals a man who is acutely aware of how he is perceived and the benefits and burdens that come with it.
He discusses how being non-threatening and affable has helped him gain widespread appeal but has also occasionally hindered others from taking him seriously. Instead of resenting this, he chooses to embrace the role while subtly expanding it—showing that kindness and depth are not mutually exclusive.
Moreover, humor becomes a means of parenting, healing, and even confronting societal challenges. Kenan uses jokes to teach his daughters, to reflect on racism, and to revisit painful memories like going broke.
He doesn’t use comedy to escape emotion but to clarify and elevate it. This fusion of humor and emotional depth is what makes the memoir resonate so powerfully.
It reminds readers that laughter isn’t the opposite of seriousness—it’s a sophisticated response to it.