Jimmy Fallon: I Didn't Expect It To Be This Brutal! The Hate Was Something I Wasn’t Prepared For!

Breaking Down Mental Struggles and Career Aspirations

Early Life Reflections

• The speaker expresses a moment of mental breakdown, questioning their life choices and feeling lost. They wrote a letter to a friend indicating their distress.

• The speaker reflects on their childhood desire to please people, which has been a consistent theme throughout their life. They were voted most likely to replace David Letterman in eighth grade.

Journey to Success

• The speaker recounts the challenges faced while pursuing comedy, including rejection and financial struggles while working at an improv venue for minimal pay.

• An audition for "Saturday Night Live" (SNL) is highlighted as a pivotal moment; despite failing initially, the speaker remained determined to succeed before turning 25.

Personal Insights and Motivations

• A discussion about understanding the speaker's background reveals that they have always had clarity about their goals from a young age.

• The desire to entertain and make others happy is emphasized as a driving force in the speaker's life, stemming from early experiences of wanting approval from family.

Family Influence

• The speaker shares memories of wanting to excel in sports and school, linking these desires back to familial expectations.

• Their strict upbringing in a Catholic household is discussed, highlighting restrictions on language and media consumption imposed by their father.

Parental Background

Family Dynamics and Emotional Expression

Tough Love vs. Affectionate Parenting

• The speaker reflects on their father's tough demeanor, noting that while he was emotionally reserved, he still expressed love in a more understated manner.

• In contrast, the speaker emphasizes their own parenting style, which is characterized by daily expressions of love and pride towards their children.

• The speaker describes their mother as the more affectionate parent who openly supported them, contrasting with the father's more stoic approach.

Memories of Maternal Support

• The speaker fondly recalls their mother Gloria as a significant source of encouragement and support throughout their life.

• They express how daily conversations with her contributed to building their confidence as an adult.

• Anecdotes about Gloria's personality highlight her warmth and ability to engage in long conversations, showcasing her role in the family dynamic.

Humorous Family Stories

• A humorous story illustrates the lively interactions between both parents, depicting them as cartoonish characters struggling to communicate effectively due to hearing issues.

• The speaker recounts a dinner outing with their mother where she insisted on going out despite his reservations about making a scene.

A Memorable Dinner Incident

• During dinner at a restaurant, an incident occurs when the mother's meal is forgotten, leading to escalating tensions over whether she should eat or not.

• After finally receiving her meal, she experiences a choking incident that draws attention from other diners and leads to chaotic attempts at assistance.

Reflections on Life and Loss

• The aftermath of the choking incident reveals both humor and concern within the family dynamic; they navigate through embarrassment while acknowledging life's unpredictability.

Insights into Comedy and Personal Motivation

The Influence of Family on Humor

• The speaker reflects on their family's unique sense of humor, describing them as "weird and funny" individuals who often made jokes, which created a mix of embarrassment and fond memories.

• When asked about whom they seek approval from the most, the speaker identifies their mother, expressing a desire to make her laugh due to her supportive nature.

• The speaker compares their relationship with their mother to that of a fan and artist, seeking feedback on new work much like a musician would with an album.

The Nature of Pursuing Comedy

• The speaker discusses the inherent risks in pursuing comedy as a career, noting its unpredictability regarding financial success or recognition.

• They emphasize that money was never a motivating factor for them; instead, they enjoyed the process of working and creating.

Early Work Experiences

• Reflecting on early jobs since age 13, the speaker mentions enjoying work for its own sake rather than for monetary gain.

• A humorous anecdote is shared about finding money in his jeans during laundry days, highlighting indifference towards finances instilled by family dynamics.

Building a Career in Comedy

• The speaker recalls how performing at venues like the Improv in LA was more about gaining stage time than financial compensation.

• They describe initial gigs where pay was minimal (e.g., $7), but stress that the experience gained from performing was invaluable for developing their comedic persona.

Memorable Moments in Stand-Up

• A significant moment is recounted when they performed at the Improv after working hard to earn stage time.

Jimmy Fallon's Early Comedy Journey

First Performance Experience

• Jimmy recalls his first performance where he had to follow a renowned comedian, expressing both excitement and pressure about the situation.

• He describes using a troll doll in his act, performing impressions of celebrities as part of his comedic routine.

• Fallon humorously introduces the concept of auditioning for Troll Productions, showcasing his ability to mimic various celebrity voices.

Developing Confidence and Goals

• He reflects on how he critiqued the dolls during his act, demonstrating an early knack for observational comedy.

• Fallon shares that he played guitar with the troll doll as part of his performance, indicating a blend of music and comedy in his acts.

Childhood Aspirations

• When asked about confidence at age 12, Fallon states he was confident but not cocky, influenced by family advice against arrogance.

• He mentions being voted "most likely to replace David Letterman" in eighth grade, which foreshadowed his future career path.

Aiming for Saturday Night Live

• Fallon clarifies that while he aimed for SNL from a young age, it ultimately led him to replace Letterman on Late Night.

• Reflecting on goal-setting, he discusses principles that could help others achieve their aspirations based on focus and determination.

The Role of Belief and Support

• He acknowledges that encouragement from peers helped solidify his belief in pursuing comedy as a career.

• Fallon expresses skepticism towards manifestation but recognizes that having clear goals can lead to success through hard work and dedication.

Steps Toward Success

• He recounts wishing every birthday to be on SNL, illustrating how personal aspirations fueled his drive.

• Discusses taking steps like doing stand-up and impressions as strategic moves toward achieving his dream role on SNL.

Journey to Comedy: From College to LA

Early Aspirations and Family Support

• The speaker reflects on their desire to connect with influential figures in comedy, such as Adam Sandler, through connections made on "SNL."

• They mention moving to LA with manager Randy Seagull, who was expected to guide them in pursuing a career in comedy.

• The speaker's father, an IBM employee, insisted on a college education as part of their agreement before pursuing comedy full-time.

• After three and a half years of college, the speaker decided to drop out and move to LA for acting lessons and auditions.

• Their parents were initially skeptical but supportive after hearing positive feedback from the manager about the speaker's potential.

Struggles in Acting and Rejection

• The speaker recounts their early experiences working at a news weekly while trying to break into comedy.

• A connection made through this job led to an opportunity with Randy Seagull, who recognized the speaker's raw talent but noted they were still inexperienced ("green").

• The speaker candidly discusses feelings of self-doubt during tough times in LA when faced with constant rejection.

• They initially resisted taking acting lessons but eventually realized the importance of learning how to perform alongside other actors.

• This realization prompted them to start auditioning for roles despite feeling unprepared.

First Auditions and Learning Experiences

• The first audition involved playing a lifeguard in "Brady Bunch 2," where they had only one line: "Get out of the pool."

• During this audition, they experienced awkwardness and embarrassment when receiving feedback that they were "too green" for the role.

• Despite repeated rejections from various auditions (around 30), their manager encouraged persistence and improvement through practice.

• The emotional toll of continuous rejection was significant; however, it served as motivation for growth rather than defeat.

The Journey to Saturday Night Live

The Pursuit of a Dream

• The speaker reflects on the possibility of working in various roles within the entertainment industry, emphasizing that persistence can lead to unexpected opportunities.

• Despite financial struggles and contemplating returning home, the speaker expresses disappointment at not achieving their dream of being on "Saturday Night Live" (SNL).

• In school, when asked about career aspirations, the speaker specifically states they want to be on SNL, highlighting the rarity and ambition of this goal.

• The desire to appear on SNL is described as an ultimate aspiration; even a single episode would fulfill a lifelong dream for the speaker.

• The significance of SNL is tied to family traditions and cultural impact; it represents the pinnacle of comedy for them.

Obsession with Comedy

• The comparison between playing for prestigious sports teams and aspiring to be part of SNL illustrates how deeply ingrained this ambition is in the speaker's life.

• Unlike many aspiring athletes who may settle for any team, the speaker's focus remains solely on SNL as their ultimate goal.

• Family bonding over watching SNL is emphasized; they were early adopters of technology like VCRs to record and rewatch episodes together.

• The speaker describes studying iconic sketches from past comedians like Belushi and Murray, showcasing their dedication to mastering comedy through observation.

• High school experiences reveal an obsession with sharing favorite sketches with friends while prioritizing watching SNL live over social activities.

Struggles with Addiction

• A personal anecdote reveals that while enjoying beer during viewing parties, it led to unhealthy habits; by age 16, drinking became problematic for the speaker.

• Despite struggles with alcoholism starting young, watching SNL remained a solitary yet passionate pursuit for understanding comedy better.

• Even during college years, attending parties was secondary to watching SNL live; this obsession defined social interactions and priorities.

Reflection on Obsession

• A visit to NBC solidified their connection with SNL; feelings of nervousness highlight how significant this dream has been throughout their life journey.

• Working at NBC since 1998 feels surreal but also serves as a reminder not to lose sight of initial passions despite routine work life.

Mental Health Struggles in LA: A Personal Journey

Coping with Rejection and Financial Strain

• The speaker reflects on their time in LA, describing a period filled with auditions and constant rejection, leading to significant mental health challenges. They express that this was one of their lowest points despite generally being a positive person.

• The speaker recalls exploring therapy options as they faced mental breakdowns, questioning their life choices and feeling isolated without friends or a social life, consumed by work and stand-up comedy.

• Financial struggles compounded the stress; the speaker felt unable to afford basic necessities like gas for auditions or food, leading them to contemplate returning home to regroup financially.

Emotional Breakdown and Support Systems

• In a moment of vulnerability, the speaker wrote a letter to their best friend expressing feelings of losing control over their life. This letter became a symbol of their emotional state during that challenging time.

• The friend still possesses the letter and humorously threatens to publish it someday. This highlights the bond between them but also underscores the embarrassment tied to such personal revelations.

Reflections on Regret and Resilience

• The speaker wishes they could offer past advice to themselves during those tough times, emphasizing messages of reassurance and pride in persevering through adversity.

• They would tell their younger self that everything will be okay and express pride in pursuing dreams despite hardships, reinforcing the importance of resilience in achieving future success.

Creative Solutions Amidst Hardship

• During difficult times, the speaker creatively repurposed cardboard boxes into makeshift furniture. This resourcefulness reflects an ability to find positivity even in bleak circumstances.

• While having cardboard furniture may seem depressing now, at that time it represented creativity and adaptability rather than despair.

Growth Through Adversity

• The speaker believes enduring these challenges ultimately made them stronger mentally. They draw parallels between physical training (like going to the gym) and building mental resilience through life's difficulties.

Reflections on School and Life Choices

The Significance of High School Experiences

• The speaker reflects on their daughters' school experiences, noting the emotional weight these moments hold for them, despite the speaker's belief that such relationships may not last.

• They express how time feels different at various life stages; while high school seems long to students, it appears trivial in hindsight.

Determination to Succeed

• The speaker emphasizes a strong conviction that they would have found a way to be part of "Saturday Night Live" (SNL), regardless of circumstances.

• They assert that there was no option but to succeed in their goal of being on SNL, indicating an unwavering commitment to their dreams.

Contemplating Alternate Realities

• Reflecting on life choices, the speaker discusses how not achieving certain goals would feel like living a lie or missing out on reality.

• They share personal anecdotes about pretending to be successful in media as a child, highlighting the power of visualization in shaping one's path.

The Role of Luck and Opportunity

• When discussing their journey towards SNL auditions, the speaker acknowledges both luck and small positive events as pivotal in reaching their goals.

• They recount securing a holding deal with Warner Brothers while ensuring they could leave for SNL if given the opportunity.

Audition Experience Insights

• The speaker describes preparing for their first audition by wearing what they considered their best outfit and performing stand-up comedy.

The Journey to SNL: Overcoming Challenges

Initial Setbacks and Determination

• The speaker reflects on a missed opportunity for a show, feeling numb after being informed they didn't get the role.

• Despite the setback, there was a strong desire to prove themselves and showcase their true abilities in stand-up comedy.

• At 23, the speaker recalls having written in a journal that if they didn’t make it onto SNL by age 25, they would consider taking drastic actions.

• They clarify that while they felt serious about their goal, deep down they believed they would succeed before turning 25.

The Path to Success

• The speaker shares an anecdote from their diary where they set goals for themselves before turning 25, highlighting the importance of ambition.

• They discuss starting multiple businesses at a young age and how this experience taught them various roles within entrepreneurship.

Tools for Modern Entrepreneurs

• A transition into discussing Shopify as a tool that simplifies business operations through AI integrations, making it easier for new entrepreneurs.

Audition Experiences

• During the second audition around ages 23 or 24, the speaker was advised not to perform their previous act involving troll dolls due to its familiarity with producers.

• They adapted their performance style but struggled with confidence during auditions despite nerves.

Memorable Moments in Auditions

• A pivotal moment occurred when the producer reassured them about Lauren Michaels' demeanor during auditions; this advice helped ease some anxiety.

• The speaker performed an impression of Adam Sandler which garnered laughter from Lauren Michaels—a significant moment that boosted their confidence.

Jimmy Fallon's Journey to SNL and Beyond

The Audition Process

• Jimmy reflects on the initial audition process, noting that he felt good about the feedback but faced a long wait for results. He mentions that they were looking for a different direction, ultimately hiring Tracy Morgan instead.

• After some time, Fallon received a call from Lorne Michaels inviting him to meet in Los Angeles at Paramount Studios, which he describes as an exciting and nerve-wracking experience.

• Upon entering Lorne's office, Fallon recalls the heavenly atmosphere and his nervousness during their conversation. Lorne asked if he wore wigs for characters, indicating interest in having him join SNL.

The Life-Changing Moment

• Jimmy was overwhelmed when Lorne expressed interest in hiring him for the show. He describes this moment as surreal and life-changing.

• After shaking hands with Lorne, Fallon immediately called his mom from a payphone to share the news of being cast on SNL, highlighting the emotional significance of this achievement.

Transitioning to New York

• Following his casting on SNL, Fallon moved back to New York City where he secured an apartment in Midtown. He expresses gratitude for this opportunity as it led to significant milestones in his career.

• After working on SNL and several movies, Fallon was invited to host Late Night and later replace Jay Leno on The Tonight Show. He reflects on how these experiences shaped his career trajectory.

Reflections on Fame

• Discussing the emotional impact of achieving his dreams after years of hard work, Fallon compares it to a triumphant moment akin to "the end of Rocky."

• He emphasizes how rare it is for someone to achieve such success and shares how meaningful it was to celebrate with his mother who always believed in him.

Challenges Faced

• Despite achieving fame, Fallon candidly discusses facing rejection and criticism throughout his career. He notes that not everyone supports you when you succeed.

• Reflecting on public perception and negativity from critics before social media became prevalent, he acknowledges that dealing with haters was unexpected but part of being successful.

• Jimmy stresses the importance of resilience against negativity while maintaining creativity despite external pressures or criticisms aimed at him personally or professionally.

Understanding Self-Acceptance and Fame

The Challenge of Seeking Approval

• The speaker expresses a strong desire for approval from others, stating, "I want everyone to like me," but acknowledges the futility in trying to please everyone.

• They emphasize that changing oneself to gain approval can lead to self-hatred, as one cannot satisfy all opinions or preferences.

Staying True to Oneself

• A quote from Mike D of the Beastie Boys is referenced: "Be true to yourself and you will never fall," highlighting the importance of authenticity.

• The speaker reflects on their experience with fame, noting it was enjoyable but also came with challenges that required personal resilience.

Navigating Fame and Creativity

• They recount a memorable moment working with Mick Jagger on a sketch, illustrating how spontaneous creativity can lead to successful outcomes.

• Despite initial nervousness pitching ideas to Jagger, they eventually found success with a concept that resonated with both Jagger and the audience.

The Process of Collaboration

• The speaker describes the collaborative process in creating sketches, emphasizing the need for quick thinking and adaptability during brainstorming sessions.

• They share an anecdote about pitching increasingly absurd ideas until landing on one that worked well, showcasing the unpredictability of creative collaboration.

Reflections on Interviews and Perceptions of Fame

• Reflecting on numerous interviews over a decade, they ponder how meeting various high-profile individuals has shaped their understanding of fame and life.

How to Make Guests Feel Comfortable?

Building Rapport Before the Show

• The speaker emphasizes the importance of making guests feel comfortable by greeting them in their dressing room before the show.

• Engaging in casual conversation about life or personal topics helps ease pressure, allowing for a more relaxed interview atmosphere.

Understanding Guest Dynamics

• The speaker reflects on their experience over 16 years, noting they have seen guests at both their highs and lows, which fosters a sense of familiarity.

• Regular interactions with guests create a feeling of continuity, as if they just saw each other yesterday, enhancing the connection during interviews.

Keeping Content Fresh and Engaging

Avoiding Boredom in Long-Term Projects

• The speaker discusses concerns about maintaining excitement after four years of podcasting but believes there are always interesting people to engage with.

• Continuous effort and creativity are essential; stopping would lead to stagnation and boredom.

The Importance of Hard Work

• Acknowledges that much of what appears on screen is staged or "fake," emphasizing that hard work is necessary to keep content engaging.

• Consistent effort is likened to daily routines like brushing teeth—it's about integrating passion into everyday life.

Challenging Oneself Creatively

Expanding Creative Horizons

• The speaker encourages pushing boundaries by seeking new challenges, such as writing original songs or children's books.

• Discusses aspirations like creating a Christmas album filled with original songs as an example of setting high creative goals.

Personal Projects and Family Influence

• Shares an idea for a children’s book aimed at encouraging babies to say "dada," highlighting how personal experiences inspire creative endeavors.

• Responding to family feedback led to creating another book focused on "mama," showcasing adaptability based on audience needs.

Reflecting on Personal History

Nostalgia Through Childhood Memories

• The discussion shifts towards childhood memories, including photos from the past that evoke nostalgia for family and friends.

Tribute to Family Influence

• Reflecting on his mother's influence, he recalls her being his best audience and expresses ongoing dedication to making her laugh even after her passing.

Home and Loss: Reflections on Relationships

The Concept of Home

• The speaker reflects on the idea that "home" is not a physical place but rather consists of people who provide emotional support and connection.

• Losing someone close, such as a mother, profoundly impacts one's sense of home and reality, highlighting the importance of relationships in life.

Grieving Process

• The speaker shares personal experiences with grief, emphasizing that memories of loved ones persist even after they are gone.

• Music often triggers memories of the deceased, evoking both sadness and joy as one recalls shared moments.

Cherished Memories

• The speaker expresses missing their mother's positive reinforcement and humor, which provided comfort and validation throughout their life.

• They reflect on how certain interactions with their mother brought happiness and material for creative expression.

Existential Concerns

• There is an acknowledgment of existential fears regarding unspoken words or unresolved feelings with aging parents.

• Despite these fears, the speaker feels they communicated effectively with their mother before her passing.

Coping with Loss

• The grieving process can be intense; however, it is essential to allow oneself to feel emotions fully to heal over time.

• As time passes, happy memories begin to outweigh sadness about loss. It’s important not to dwell solely on what is lost but also appreciate what was gained from the relationship.

Impact on Life Perspective

• The loss has shifted the speaker's perspective on work; they now find motivation in honoring their loved ones through their endeavors.

• They continue to think about how their actions would make their mother proud, indicating that her influence remains strong in their life choices.

Health Considerations Post-Loss

• Turning 50 has prompted reflections on health and longevity; concerns arise from witnessing unhealthy habits in parents during childhood.

Health and Longevity Journey

Personal Health Insights

• The speaker reflects on past attempts to incorporate fitness into their life, mentioning multiple purchases of a treadmill that ultimately went unused.

• They emphasize the importance of eating better and staying active, noting daily walks and reduced alcohol consumption as part of their health journey.

• The speaker expresses a desire for longevity but also acknowledges the complexities of aging, wanting to enjoy life without outliving peers.

Matcha Latte Launch

• Introduction of a new product: canned matcha lattes developed over four years due to complex challenges in the business process.

• The matcha lattes are described as barista-quality drinks available in vanilla and strawberry flavors, emphasizing their natural sweetness and creaminess.

• The speaker shares personal reasons for drinking matcha, highlighting its sustained energy benefits compared to other products.

Future Plans and Media Landscape

Community Engagement

• Announcement of a new private community called "D of a CEO," inviting 10,000 members for exclusive content and direct access to the speaker.

• Members will have opportunities to influence show content by suggesting guests and topics for discussion.

Thoughts on Media Evolution

• Discussion about potential future directions beyond traditional media; however, the speaker feels comfortable with their current role in television.

• They argue that despite claims about TV's decline, it remains powerful with high-quality entertainment still being produced across various platforms.

Entertainment's Role

• The speaker believes that entertainment serves as an essential outlet for people seeking distraction or creative engagement from everyday problems.

The Joy of Creating: A Conversation with Jimmy

The Concept of "Holiday Seasoning"

• Jimmy discusses his Christmas album titled "Holiday Seasoning," aiming to create a new verb that encapsulates the spirit of celebrating various holidays together.

• He expresses hope that the term "holiday seasoning" might catch on in the future, suggesting a collective celebration across different cultures.

Philanthropy and Fun Products

• Jimmy highlights his collaboration with Serious Fun, a charity benefiting from sales of his ice cream flavor, Tonight Dough, emphasizing its dual purpose as both enjoyable and charitable.

• He mentions creating unique sneakers called Gobstompers, which change color as they are worn, making each pair distinct to the wearer.

The Pursuit of Happiness

• The conversation shifts to Jimmy's overarching goal: making people happy through various creative endeavors like rides, ice cream, and innovative products.

• He reflects on how this pursuit aligns with his personal life and values.

Fatherhood's Impact on Perspective

• Jimmy shares insights about becoming a father and how it has transformed his view on life and relationships with children.

• He notes an increased empathy towards other kids and parents, highlighting a newfound patience for situations he once found frustrating.

Life Lessons for His Daughters

• When asked what advice he would give his daughters for living well, he emphasizes kindness, generosity, and pursuing their passions as keys to success.

Misunderstandings in Public Perception

• Jimmy addresses how he feels misunderstood by others who may perceive him as carefree or lacking direction when in reality he is thoughtful about his work.

Legacy Reflections

• If given the chance to inscribe a message on his gravestone, Jimmy would choose "he had a good time," reflecting his desire for joyfulness in life experiences.

Acknowledgment of Influence

• The interviewer expresses admiration for Jimmy’s positive impact on others' lives amidst societal challenges like division and negativity online.

Closing Thoughts and Reflections

Gratitude and Tradition

• The speaker expresses gratitude towards the cameras, emphasizing a sense of appreciation for the experience.

• A closing tradition is introduced where the last guest leaves a question for the next guest without knowing who it will be directed to.

Deep Philosophical Question

• The question posed to the speaker is profound: how would their self-perception and behavior change if they learned that reality is subjective, based solely on their actions?

• The speaker reflects on this idea, suggesting they might take credit for such a realization, indicating an awareness of personal agency in shaping reality.

Simulation Hypothesis

• There’s speculation about whether life could be a simulation, with thoughts on whether those controlling it are engaged or have moved on from interacting with characters like themselves.

• The analogy of "Toy Story" is used to illustrate the notion that creators may forget about their creations, leading to characters living independently.

Final Remarks and Engagement

• The speaker thanks their host warmly and appreciates being part of the conversation, highlighting enjoyment in sharing ideas.