Key Takeaways
1. My Family is Wildly Unique and Unfiltered
Nothing is as equally frustrating and recognizable as my dad’s absolutely insane social skills.
Dad's unique communication. The author's father, a retired Marine Corps Captain, has baffling social habits, frequently walking away from conversations or hanging up the phone abruptly when he gets bored, a trait he claims he's "gotten much better about" despite evidence to the contrary. Beyond social disengagement, his primary conversational topics revolve around his digestive tract, detailing bowel movements, fart smells, and even naming specific shitting incidents like "Orlando Airport" or "Cherry Bombs."
Mom's directness and cultural clash. His Peruvian mother, who married his father speaking limited English, is equally unfiltered, often criticizing appearances, life choices, and eating habits with brutal honesty, sometimes using terms considered offensive in North America. Despite their glaring differences—his father's "savage" nature (burps, farts, chicks, guns) versus her anxiety, manners, and devout Catholicism—they stayed together, often citing their shared faith. Their communication styles, particularly his mother's heavily accented English and his father's bluntness, created a chaotic but often hilarious environment.
Pointing out the absurdity. Growing up, the author found perverse pleasure in highlighting his father's gross habits to provoke his mother's disgusted reactions, a dynamic he continues to find hilarious. This family environment, marked by extreme personalities and cultural misunderstandings, shaped his own comfort with pushing boundaries and finding humor in the repulsive, despite his mother's frequent bewildered question, "Why does it give you pleasure to be so disgusting?"
2. Childhood Dreams Don't Always Match Reality
I knew that it looked like shit, but I must have thought that other kids would have shitty presentations too.
Early academic struggles. The author harbored dreams of becoming a doctor, despite early signs like a disastrous fifth-grade science project where his sun-picture experiment earned the sole "Participation Award" among elaborate, interactive displays. His terrible handwriting and lack of scientific detail stood in stark contrast to his peers, revealing a significant gap in academic aptitude he didn't fully grasp at the time.
A medical reality check. The dream persisted, even leading him to shadow surgeons at the Mayo Clinic at age fourteen. This experience, starting with an awkward observation of a vaginal cyst removal on an awake patient (complete with his father's inappropriate commentary), exposed him to the graphic realities and early hours of the medical profession. Witnessing multiple procedures on various organs over nine hours solidified his realization that this path was not for him, regardless of his family's medical legacy.
Football dreams deflated. Shifting his focus to football, he showed early promise, even starting as a freshman on varsity in Florida, a state with elite high school football. However, his commitment wavered when faced with intense summer training, opting instead for his traditional summer trips to Peru. Gaining thirty pounds from protein shakes and inactivity moved him to the offensive line, and his poor academic record, particularly failing Algebra twice, ultimately derailed his college football aspirations when a DIII school required a summer math class he refused to take.
3. Finding Identity in Unexpected Cultures
It was like a portal into a world my friends and I didn’t know existed.
Hip-hop obsession. Growing up in the bland suburbs, hip-hop provided an exciting, cool, and seemingly dangerous portal into a world distinct from his own. Heavily influenced by Black artists in music and sports, he developed an early obsession, even wishing he were Black, desiring the style, athleticism, and cultural coolness he saw glamorized. This led to attempts to immerse himself, including using a library book's slang to write and perform awkward, slang-filled rhymes for anyone who would listen.
Peruvian immersion. Spending summers in Peru from age nine forced him to navigate being an outsider due to his appearance ("gringo") and learn to earn respect. Living with family and attending school there exposed him to a different pace of life, late nights, and a culture that felt both exciting and dangerous, including experiencing terrorism firsthand. This immersion, despite the challenges, fostered a deep connection to Peruvian culture, family, and its renowned cuisine.
Cultural appreciation vs. appropriation. His deep love for Black American culture, from music icons like the Fat Boys and Chris Rock to sports figures like Deion Sanders, shaped his identity and career path, particularly in comedy. He acknowledges the complex dynamic of a white person embracing and being influenced by Black culture, contrasting genuine appreciation with appropriation, and ultimately celebrating the richness and "dope"-ness of Black excellence that resonated with him from a young age.
4. Life Lessons Come From Absurd Encounters
I wanted to know and to feel that I had a purpose.
The lost wallet quest. While working at America's Most Wanted in DC, a chance encounter in a cab led him to find a lost wallet. Driven by a romanticized fantasy of a feel-good, life-changing moment, he embarked on a quest to return it, only to be met with indifference from the owner's father ("He's a real asshole") and, months later, a completely detached reaction from the owner himself, a waiter named Justin, who showed zero gratitude or curiosity.
Bank photo incident. Attempting to set up his friend with a beautiful bank teller, he secretly took photos of her, leading to a call from Wells Fargo security. He was forced to delete the photos and informed he was placed on a national "potential threat list" shared among all US banks, a consequence he found both terrifying and absurd, especially given his friend's initial skepticism about the teller's attractiveness.
The "relaxation spa" reality. His first job in LA as a "spa attendant" at a place called "Splash" quickly revealed it wasn't a spa at all, but an hourly rental spot primarily used for paid sexual encounters. Cleaning up after customers and observing the awkward, often transactional meetings provided a bizarre form of people-watching, further exposing him to the strange and sometimes sad realities of human behavior outside the mainstream.
5. The Unfiltered Reality of Being a Road Comic
There’s no business like show business. And if show business doesn’t want you, there’s always comedy.
The grind and the pay. The path to becoming a successful touring comedian is arduous, involving countless shows in often less-than-glamorous locations. Early in his career, pay was minimal ($50 for MCs, $100 for features), often requiring other jobs to make ends meet, from working in restaurants to digging ditches. Comedy clubs frequently house comics in poorly maintained "comedy condos," a tax write-off for owners, sometimes leading to uncomfortable or even terrifying roommate situations.
Travel and venues. The job involves extensive travel to diverse locations, from Winnipeg in winter to Phoenix in summer, performing in various unconventional venues like dive bars, parking lots, and even a memorable, anxiety-inducing trip to perform for military personnel at Guantanamo Bay, where he encountered a seemingly aloof CIA officer. These experiences highlight the non-glamorous side of the profession, far from the audience's romanticized view of travel.
Dealing with hate. As visibility grows, so does negative feedback, particularly online. While initial feedback is often supportive, professional comics face constant criticism and hate mail, which can be emotionally taxing despite developing a "tolerance" over time. The author recounts a specific instance of receiving thousands of angry messages from Louisiana after joking about the state, leading him to invent an assistant persona ("Blake") to humorously engage with the outrage.
6. Sometimes It's Good to Be Fat
You’re two hundred fifty pounds. That’s a lot. Sometimes it’s good to be fat.
Early drug experimentation. The author's drug use began moderately with weed in high school, but escalated to ecstasy and, significantly, GHB ("G"). Initially drawn to GHB by the false belief that bodybuilders used it, he became fond of its euphoric effects, even using it during school hours with surprising impunity. A blackout incident after a Clint Black concert served as a warning, but didn't deter him.
College escape and overdose. Bringing a large supply of GHB to college, he used it frequently to cope with loneliness and disappointment about his school choice. This led to his supply running out and seeking out a weaker, diluted version locally. A return home for Thanksgiving led to mixing a large amount of GHB with numerous screwdrivers, resulting in an overdose and an eight-hour coma.
Survival and the doctor's explanation. Waking up in intensive care, restrained and with tubes, he faced his disappointed parents and doctors needing to know what he took. His toxicology report showed a mix of barbiturates, amphetamines, and cocaine, indicating the drugs he took were spiked. The doctor who saved him attributed his survival, in part, to his weight, stating, "You're two hundred fifty pounds. That's a lot. Sometimes it's good to be fat," a stark and memorable explanation for surviving a near-fatal mistake.
7. Celebrity Encounters Are Often Absurd
I mean I don’t have on makeup and we just flew, but… okay.
Unexpected flight neighbors. The author has had several memorable encounters with celebrities while flying, often seated next to them in first class. These include sitting across from Bruce Bruce, who surprisingly revealed a deep obsession with Andy Griffith and his museum, and sitting next to Chris Tucker, whose first words upon boarding were "Should I do another Rush Hour?"
Serena Williams and the bit. A particularly striking encounter was sitting next to Serena Williams. They had a pleasant conversation, and she even wrote down his name and Netflix special title. He later realized with horror that his special contained a joke about a threesome fantasy involving her and her sister, leading to anxiety about her potentially watching it. Running into her years later, he drunkenly recounted the story, which her husband found hilarious, while Serena remained politely amused.
The Mr. Big effect. Flying next to Chris Noth highlighted the intense level of celebrity fixation, particularly from women who were fans of Sex and the City. Witnessing a flight attendant become visibly trembling and incapable of performing her job due to his presence was a striking example of this phenomenon. Noth himself seemed resigned to this constant attention but was engaging in conversation, surprisingly expressing passionate admiration for the TV show Downton Abbey.
8. Embrace Your Inner Child and Abnormal Behavior
You like abnormal human behavior.
Podcast clip fascination. On his podcast, Your Mom's House, the author and his wife specialize in finding and sharing outrageous, disturbing, and inappropriate internet clips, often aiming to provoke strong reactions from guests. This fascination with abnormal human behavior is a core element of the show, fueled by listener submissions that push boundaries beyond imagination.
Dr. Drew's insight. Discussing this interest with Dr. Drew Pinsky, the author initially claimed it was "studying human behavior," but Dr. Drew quickly corrected him, stating he liked "abnormal human behavior" and pointing out the author's visible shame about it. This moment forced a reflection on why watching strange or uncomfortable clips brings him happiness and laughter.
Laughing at injuries. A long-standing, involuntary reaction for the author is laughing uncontrollably at stories or videos of personal injury, particularly blunt force trauma or falls, though not gory ones. He traces this back to childhood squirming and a construction job where a coworker's story of a bathtub falling on his neck from three stories up triggered an intense, seizure-like fit of laughter, a reaction the coworker eventually found amusing. This seemingly dark humor is a deeply ingrained part of his personality.
9. Fatherhood Reveals Yourself in Unexpected Ways
I’d like to play alone, please.
Parental favoritism. Growing up, the author and his sisters wondered if their parents had favorites. While his mother openly stated she loved his sister Jane the most because Jane loved her the most, his father consistently told the author he was his favorite, a declaration that felt genuinely good. Now a father himself, he understands the temporary favoritism based on behavior ("whichever kid isn't crying").
Contrasting personalities. His two sons, Ellis (6) and Julian (3), have vastly different temperaments. Ellis is demanding and risk-taking, showing a fascination with watching snakes hunt and eat, a behavior the author finds oddly familiar and intense. Julian is easygoing but has recently started rejecting his given name, insisting on being called a rotating list of absurd names like "Mr. Parking Lot" or "Blender," which the author finds both challenging and hilarious.
Seeing himself in his sons. Julian's rapid language development and correct verb conjugation at a young age were astonishing. Ellis, though slower to develop language, delivered his first full sentence to his father: "I'd like to play alone, please." This mirrored the author's own childhood preference for solitary play and his adult need for alone time, a trait he has built his life around. Seeing his own quirks and sentiments reflected in his sons, even the less polite ones like "Go away!", creates a profound sense of connection and often leads him to think, "This is my favorite son," albeit temporarily.
10. Don't Wait, Make Your Dreams Happen
The only thing I did was believe I could do it, and I took action.
Pursuing the special. After ten years in comedy, the author wanted a one-hour special to gain visibility and sell tickets, but major networks like Comedy Central weren't interested. Instead of waiting, he took a DIY approach, recording an audio album, "White Girls with Cornrows," himself and distributing it online, allowing him to earn money and own his work, a path he encourages other artists to take in the digital age.
Comedy Central rejection. He eventually got the chance to perform his hour for Comedy Central executives, but was rejected because it lacked a "theme," a feedback he found absurd ("The theme is funny jokes"). This rejection of his dream platform was a significant disappointment, highlighting the subjective and sometimes baffling nature of the entertainment industry.
Netflix opportunity and unexpected success. A smaller company, Comedy Dynamics, offered to shoot his special, "Completely Normal," on spec. Though initially feeling like a consolation prize compared to Comedy Central or HBO, he accepted. When Netflix, then a relatively new streaming platform, licensed it, he was initially underwhelmed. However, months after its release, he noticed a significant and unexpected increase in ticket sales, realizing the special had finally achieved the goal of boosting his road business, proving that taking action and seizing unexpected opportunities can lead to success, even if not on the initially desired path.
11. Language Evolves, But Some Words Stick
“I’m retarded.”
The evolution of language. The author reflects on how language changes, with words once common becoming offensive over time, citing "Oriental" as an example that society largely agreed to stop using for people without significant pushback. He contrasts this with the word "retarded," which, despite efforts to deem it unacceptable due to its association with developmental disabilities, persists widely in casual conversation with a secondary meaning of foolishness or absurdity.
Hypocrisy and personal use. He notes the hypocrisy of people vehemently opposing the word while it remains prevalent, arguing that the strong reaction suggests people are more attached to policing its use than they were with terms like "Oriental." He admits to using the word himself, often in self-deprecation or to describe absurd situations or people, finding it a concise way to express extreme foolishness.
A relatable example. Using a personal anecdote about frantically searching for sunglasses only to find them on his head, he describes his immediate reaction: "I'm retarded." His wife's agreement ("You are the most retarded. But I love you") highlights how the word is used in a context unrelated to developmental disability, serving as a punchline for extreme, self-inflicted foolishness. He argues that while language should evolve, the strong, often performative, backlash against this specific word feels different from other linguistic shifts.
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Review Summary
I'd Like to Play Alone, Please receives mixed reviews, with an average rating of 4.01 out of 5. Fans of Tom Segura's comedy appreciate his humor and storytelling, finding the book hilarious and entertaining. However, some readers criticize the recycled content from his stand-up and podcasts, as well as the crude humor and name-dropping. The audiobook narrated by Segura is highly recommended. While some praise his personal anecdotes and celebrity encounters, others find the content offensive or lacking in originality. Overall, the book seems to appeal more to existing fans than new readers.
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