Episode 348 · Post-Ben
Tom Segura & Christina P. | The Tim Dillon Show #348
with Christina P. and Tom Segura
May 28, 2023 · 1:06:57 · 1,400,000 views · 25 segments, 149 moments indexed
Tim visits Tom Segura & Christina Pazsitzky at YMH Studios in Austin. The three discuss trans issues, why Tim was allowed to smoke growing up and the release of his new book ‘Death By Boomers.’
Watch on YouTubeDiscuss on Reddit
- 2 min
Getting Tim Dillon to Finally Do This Interview
#Tim jokes with Christina and Tom about how long it took to book them, and how he uses honest excuses to get out of hangs while comedians use elaborate lies.
5moments
- Host introduces Tim Dillon Show with two special guests they've been trying to book for six years.
- Tim acknowledges he could have done 90 hours of broadcasting or started a podcast in the time it took to secure this interview.
- Tim admits his repeated unavailability was genuine — he really was gone touring, not just making excuses like other busy people do.
- Tim confesses he's a bad liar because his Instagram story contradicts his claims about not being in New York.
- Host observes that declining podcast appearances has become an art form in the comedy world.
- 2 min
Using His Schizophrenic Mother as an Excuse
#Tim describes using his institutionalized, schizophrenic mother as a permanent excuse to get out of obligations, including the government phone she can't use.
7moments
- Tim uses his mother's mental institution stay as an excuse to get out of things, though she's been unwell for 30 years straight.
- His mother is morbidly obese and schizophrenic, so if she opens her room door by herself, that counts as a win.
- He claims to visit his mother to spend time with her, then immediately admits he's joking and only goes four times a year.
- His mother forgets he's there when he visits, making the whole trip questionable in terms of actual connection.
- Tim's aunt texts him that his mother has the phone but doesn't know how to use it and they'll need to teach her.
- Tim refuses to help teach his mother the phone, arguing that at 70 years old, if she can't use it they should write it off.
- He doesn't even have his mother's phone number saved in his contacts.
- 2 min
Christina's Racist Dead Mother and the Security Guard
#Christina tells the story of meeting her deceased mother's building security guard, who reassures her that her mother never used a racial slur toward her specifically, implying she used it on others.
6moments
- Tim's mother was racist, and schizophrenic like he is
- Security guard told Christina her mother never called him the n-word, implying she called other people that
- Tim doesn't think his mother uses the n-word yet, but suspects she'll get there
- Tim's mother told him as a child to tell people she was dead if he needed to get out of something
- Saying a parent is dead functions as a universal cancel clause among parents with kids
- Many comedians can't use the dead parent excuse because they're single, and some go the pedophile route instead
- 2 min
The Pedophile Excuse and Kids' Friends' Boring Parents
#Riffing on parental excuses to cancel plans, they discuss how comedians' social bar is so high from hanging with other comics that normal parents at kids' events are unbearable.
5moments
- Tim asks if their kids have friends whose parents are actually cool.
- Tim describes the best part of being a comedian: hanging out with other comedians and the parking lot hangs after sets.
- Children's parties at Chuck E Cheese force small talk about weather and summer plans, which Tim says he'd rather die than participate in.
- When people ask Tim if he has new comedy material, he can't understand what they're even asking.
- Tim notes having children is a problem because he'd want to spend a lot of time with them, like Bert does.
- 2 min
Wanting Alt-Right Reactionary Kids and a Cold Asian Son
#Tim jokes about wanting to raise terrible, wealthy, reactionary children later in life, while Christina describes her cold, high-achieving Asian son who dominates academically and athletically.
6moments
- Tim imagines raising one or two wealthy alt-right reactionary podcast psychopaths as children, admitting the idea excites him.
- He predicts he'll have kids in his 50s when his testosterone drops, since he's too busy at his peak now.
- Tim's hypothetical child is Chinese, which he praises as intelligent and competent.
- The kid is extremely cold and doesn't attach to his parents, showing no emotion when dropped off at school.
- Asian kids dominate academically and athletically—one girl in his school had a 4.2 GPA, classical piano training, and dominated the swim team.
- Tim jokes he wants his kid to be a trans athlete.
Asian children
- 2 min
Wanting a Trans Athlete Kid and the Leah Thomas Controversy
#Tim fantasizes about having a controversial trans athlete child like Leah Thomas, leading into a discussion of blown swim records, and a tangent about Tim's own gay awakening on his childhood swim team.
6moments
- Tim jokes about wanting his kid to be embroiled in a massive controversy like Leah Thomas, comparing it to being a boundary-breaker.
- He doesn't agree with Leah Thomas taking girls' swimming titles but finds it funny seeing female swimmers exasperated about the situation.
- Tim notes that a top-ranked swimmer's records were obliterated by Thomas, who ranked 700th as a male before transitioning.
- He reveals he was on a swim team for years and his mother was a swim coach, though he's since left that path.
- Tim describes seeing an older boy named William with fully developed genitalia at age eight or nine on the swim team, which he hadn't seen before.
- Swimming is a very weird, crazy gay sport, Tim concludes.
- 4 min
Swimming's Weird Culture War and Trans Swimmer Aerodynamics
#They joke that swimming is a low-stakes battleground for trans debates, riffing on shaved bodies for aerodynamics, hormone use, and comparing Leah Thomas's noticeable effort versus Dylan Mulvaney's.
9moments
- Nobody cares about swimming until it becomes a cultural battleground with people demanding respect for being ranked third in the freestyle.
- Tim proposes that trans swimmers should cut off their penis if they want aerodynamic advantage in women's competition.
- Congress will eventually mandate penis removal as a baseline criterion for women's swimming teams.
- Lia Thomas didn't try at all to look female, just showed up in a bathing cap without any effort compared to Dylan Mulvaney.
- Dylan Mulvaney was an effeminate gay man on Broadway who transitioned and documented it daily on a blog during COVID.
- Tim's parenting advice: if your kid transitions, you have to tell them to actually try—get tits, do nails, style hair properly.
- Older men transitioning should start with a facelift because they look like droopy Basset Hounds or oil tanker workers.
- Caitlyn Jenner spent money on quality surgical work and is the model for how to transition late in life.
- Caitlyn Jenner immediately opposed gay marriage and endorsed Donald Trump after transitioning, undermining trans acceptance.
Caitlyn JennerDylan MulvaneyLia Thomas
- 4 min
The Trans Community Should Copy Caitlyn Jenner's Playbook
#Tim argues trans people could win over conservatives the way Caitlyn Jenner did by opposing gay marriage and supporting Trump, and jokes that trans people and non-binary activists should be hotter and adopt conservative talking points to win acceptance.
10moments
- Tim wonders why the trans community hasn't adopted a more conservative political strategy like Caitlyn Jenner's approach to gain acceptance.
- If moving into a straight community, he'd distance himself from Stonewall activists by suggesting some of them were 'acting up' and needed to be thrown under the bus.
- Trans people merged with the fat people, which was a mistake—gay men succeeded because they came out looking athletic and hot before slowly introducing diversity.
- Sam Smith example: you can't announce you're non-binary while looking like an overweight plumber in lingerie and expect acceptance from Americans.
- Strategy should be rolling out only the hottest trans people first to fool the public before introducing the rest of the community.
- Partnering with Bud Light was a disaster and proved trans people shouldn't make those kinds of corporate deals.
- Tim's ideal approach: attractive enough that he'd unknowingly sleep with someone who then reveals they're trans, effectively 'fooling' him.
- Parents aren't afraid of hot trans kids—they're afraid of teachers turning their children into 300-pound trans communists.
- Non-binary community would gain traction if obese girls with purple hair stopped seeking welfare and started telling people to get jobs instead.
- If marginalized groups adopted conservative anti-welfare positions, Republicans would agree with them politically while disagreeing on social safety nets.
- 1 min
Tim reads a Helix Sleep ad about his own mattress experience, his miserable friends loving it, and the trial/warranty details, directing listeners to a discount link.
4moments
- Tim was initially skeptical of the Helix mattress but became a believer after sleeping on it.
- His visiting friends are unusually happy on the mattress, despite being generally miserable and resentful people.
- Helix offers a hundred-night trial and a ten to fifteen year warranty so you can test the mattress at home.
- Current promotion: twenty percent off all mattresses and two free pillows at Helix sleep.com slash Tim D.
- 5 min
Kids as Hope vs. Gen X Toughness
#They discuss whether children represent hope for the future, contrasting Gen X's pride in toughness with younger generations' emphasis on acceptance, and whether validation-seeking culture is an illusion.
7moments
- Tim on why parents with kids need hope for the country and how children provide distraction from hopelessness.
- Wondering if his parents ever saw him as hope while admitting he was gay, on cocaine, stealing money, getting fatter, and supporting the Iraq War.
- Gen X pride in being tough and bullied contrasts with younger generation's focus on acceptance and love.
- The concern with modern kindness culture: it creates the illusion that self-concept depends on others' validation instead of inherent toughness.
- Not everyone will accept you, and that rejection is actually reality—pursuing universal acceptance is a wasted effort.
- Gen X virtues included not caring what people thought; that's now completely gone.
- Millennials brought striving and need for external validation—ribbons, praise, checklists, right schools and internships—creating exhausting careerist vessels.
millennialsGen XIraq War
- 3 min
Millennial Strivers and the Emptiness of 'End Racism' Signs
#Tim argues millennials created an exhausting, checklist-driven, approval-seeking culture (pronouns in email signatures, BuzzFeed quizzes) and mocks vague virtue-signaling like 'End Racism' signs in cities that don't need them.
6moments
- Tim identifies millennials manufacturing culture through constant self-grading—BuzzFeed quizzes, fatphobia tests, moral purity checks.
- Bookstores in Austin and San Francisco plaster inclusive slogans and 'End Racism' signs in cities that don't need convincing.
- Tim questions what 'End Racism' actually means—a slogan with zero action plan, designed to make you feel good and move on.
- The phrase has no real-world implication; people already nodding along aren't racist, and actual racists ignore it entirely.
- Christina talks about raising her kids Gen X style—competitive and aggressive—while Tim notes it's heterosexual and specific to her parenting.
- All cultural messaging feels performative, and nobody actually buys into it despite everyone claiming they do.
- 1 min
Christina introduces her book 'Death by Boomers: How the Worst Generation Destroyed the Planet But First a Child,' describing its premise as a loving but brutal takedown of boomer parents.
4moments
- Tim wrote a book and is bringing it up now because it will get better views.
- Christina's book, Death by Boomers, just got a paperback release.
- Christina wanted to capture one more disgraceful moment with her parents before they died.
- Boomers are funny—deep, selfish, narcissistic monsters sent to destroy the Earth and Society.
- 4 min
Boomer Parenting Horror Stories: Smoking Compliments and Handcuffed Guests
#Christina and Tim trade stories of boomer parental negligence and callousness, including her father praising her for never smoking a cigarette down to the filter, and a friend's parents' unfazed reaction to police arresting a fugitive from their house.
10moments
- Boomers viewed their children as obstacles to their own success, jealous when they failed and often setting them up to lose.
- Once they got technology, they immediately used it to spread hate, division, and fear because they believed that benefited them.
- Tim's father's response when Tim said he was drinking at bars every night: old men at bars have always played a role in family life.
- Smoking cigarettes at 13 in the front seat of his car, Tim's father complimented him for never smoking cigarettes down to the filter.
- That backhanded compliment about cigarettes is the kind of thing kids internalize to develop their sense of self-worth.
- Tim compares his childhood extortion tactic—threatening suicide to get his way—to how trans kids now operate.
- Friend Ryan was dating a stripper on Indiana's Most Wanted, doing identity theft and bad stuff around the state.
- State troopers came to the house, and Ryan immediately told them the girlfriend was in the kitchen; they arrested her in cuffs.
- That same night at dinner, Ryan's Boomer mother was unfazed and immediately started talking about buying a condo in Naples, Florida.
- The Boomer parents were completely crazy and detached from reality even as a criminal was being led out of their house in handcuffs.
- 4 min
Being the Overlooked Only Son Among Sisters
#Christina describes her parents lavishly praising her sisters while introducing her brother Tommy as simply 'he's nice,' and Tim shares his mother's blunt admission she wanted another child and blamed his father for denying her.
8moments
- Boomers were raised by people born around 1910 with no emotional skill set, essentially like dogs.
- Boomers have an interesting victimhood complex and are always aggrieved about something.
- Tim's father would tell him things like 'never overestimate your value' and 'what you do someone else will do too' while driving.
- When his parents introduced their three children to people, they'd describe his older sister as an A-student and great athlete, his younger sister as adorable and sweet, and then just say Tim was nice.
- Tim's mother called him in to say she always wanted another child and wasn't sure the marriage would work because his father didn't give her one.
- Parents should be criticized from a valid place, but people are not one-dimensional—his mother was both a horrible person and a great person.
- His mother was a swim coach who taught him to swim a mile in the bay at age six and trained neighborhood kids at 5 a.m.
- His mother was committed to his acting career from age seven until he was about twelve.
- 2 min
Christina's Childhood Acting Career and Touring in Annie Get Your Gun
#Christina recounts touring for months as a child actress in Annie Get Your Gun with her mother, singing an Irish folk song with lewd lyrics, before drifting into early drug use as a teen.
4moments
- Tim toured for four months with Christina in a production of Annie Get Your Gun.
- He was put in an Amstel Light shirt and sang a song about oral sex during the tour.
- Christina went insane and they separated, but Tim started using cocaine and weed at age 12 or 13.
- His friend's mother was a hooker who sold her garage, and they loved her.
- 1 min
Tim reads an ad for Bespoke Post's monthly subscription box, describing the gardening tools he received and the discount code for new subscribers.
5moments
- Tim describes the appeal of getting a Bespoke Post Box of Awesome each month—the surprise arrival filled with carefully chosen gear from small brands.
- He shows off this month's contents: outdoor and gardening items like a shovel and hoe, and explains why he likes getting his hands in with flowers and plants.
- Box of Awesome offers collections for every part of life—camping, cookouts, drink games—and works as a recurring gift for someone moving or going to college.
- New boxes release monthly across different categories, valued at seventy dollars, with ninety percent sourced from small and up-and-coming brands.
- Sign-up is free, you can skip or cancel anytime, and the code Tim Dillon gives 20 percent off the first box at box of awesome dot com.
- 2 min
Tim reads the Morgan & Morgan injury law firm ad, then drifts into confessing his own history of five car accidents, three of which he fled the scene of.
4moments
- Tim recalls a car accident where he decided not to hire a lawyer, explaining he made a left turn from the right lane and nearly killed someone while buying Vicodin in a Freeport parking lot.
- The other person in the accident told him to make the left turn, which Tim argues makes her partially liable.
- Tim admits he's been in five accidents, totaled five cars, and left the scene of three of them.
- In one hit-and-run, he rear-ended a woman, she started screaming, and he drove away really fast around her.
- 6 min
Christina describes shooting a small role in a major film alongside huge stars, getting repeatedly berated by a famous director for messing up blocking and line delivery, while refusing to name the project.
7moments
- Tim lands parts in Eli Roth's Thanksgiving and a mysterious big-deal movie where the director yelled at him.
- On set with a very big director and a very big star, Tim receives hyper-specific blocking instructions: slide the book, deliver lines at exact moments, wait the right amount of time.
- Tim kept getting his line wrong and the director repeatedly corrected him, saying "you've never said it but maybe next time you'll say it."
- The director confronted Tim directly: "What the fuck are you doing? I don't understand what's happening. You have to do this the same way every time."
- Tim reveals the mystery film is the Oprah Winfrey story, then immediately hesitates and considers cutting it from the episode.
- Tim defends the director's harsh approach, saying he deserved criticism and respects getting pushed by a great filmmaker working on a prestigious production.
- By the end of the day Tim got his scene to a good place, realized he misses acting, and believes his performance came together well despite the rough beginning.
- 3 min
Christina discusses being fired as a writer from Chelsea Lately, and both compare how writers' room jobs offer safety but stand-up offers more freedom and excitement.
5moments
- Tim was fired as a writer from Chelsea Lately, which he didn't see coming.
- He never wanted to pursue TV writing jobs despite doing a few pilots.
- Writers who take TV jobs for security are like indoor cats—they lose their edge as comedians.
- Tim found writing rooms boring compared to the freedom and excitement of stand-up performance.
- His ego hated when jokes he wrote were performed by someone else on camera.
Chelsea Lately
- 2 min
Friends with the Billionaire Streaming CEOs During the Writers' Strike
#Tim jokes about being close friends with streaming executives like David Zaslav and Ted Sarandos while claiming to support the striking writers, and fantasizes about AI replacing them.
5moments
- Tim claims to be best friends with David Zaslav, Ted Sarandos, and all the major streaming CEOs.
- He describes the awkward position of wanting to support striking writers while being close with billionaire executives.
- Tim jokes that he's often in cars with streaming company CEOs discussing how to eliminate writers.
- He admits AI is scary but also exciting because robots could replace all the writers currently doing the work.
- Tim fantasizes about a streaming CEO accidentally driving into a picket line.
- 2 min
Matt Rife and the Battle for LA Comedy Supremacy
#Tim jokes that he and Matt Rife are indistinguishable rival comics fighting for dominance of a depleted LA comedy scene, blaming bad weather and comics fleeing the city.
6moments
- No one in America cares about this story at all.
- All the good comics have left Los Angeles; most of them are gone.
- It's really a fight between two brothers who are the same person trying to reach people.
- Tim and Matt look identical; the problem is the cameras aren't nice enough.
- Rogan invested all the money in deer antlers instead of cameras.
- LA right now is just Tim and Matt fighting for supremacy.
- 2 min
Dating Kate Beckinsale Joke and Comedy Getting Too Cool
#Christina jokes about dating Kate Beckinsale being conversationally empty, before pivoting to Colin Quinn's idea that comedy always suffers when it becomes 'too cool.'
6moments
- Tim's audience is all women who voted for Joseph Biden.
- Tim and Matt Ruff get along despite being doppelgangers and it's tough to see each other all the time.
- Tim dated Kate Beckinsale and had to fill all the conversation at dinner because she had nothing to say.
- If you try to talk to Kate Beckinsale about Ukraine, you'll be disappointed.
- Comedy is getting too cool and becoming like reality TV.
- Comedy shouldn't get too cool or it loses something.
Joe BidenKate BeckinsaleBig JayShane MullenMattColin Quinn
- 1 min
The Comedian's Job Is to Remember Humans Exist
#Tim riffs on comedians needing to stay grounded in humanity rather than chasing coolness, contrasting real cool figures like Keanu Reeves and Anthony Bourdain with comics.
3moments
- Tim argues the job of a comedian is to remember that human beings exist.
- He admits it's the dumbest thing but it sounds profound when he says it.
- Tim explains comedians can't be the coolest version of themselves — cool enough to hang out with, but not untouchable like Rogan or Keanu Reeves.
Keanu ReevesAnthony BourdainJoe Rogan
- 3 min
Admiring Casey Anthony's Free Spirit
#Tim confesses admiration for Casey Anthony's carefree post-trial lifestyle, joking about her Disney World photos and imagining what she'd be like to date.
6moments
- Tim admits he likes Casey Anthony and her free spirit.
- Tim interprets her courtroom expression as playing coy about the situation.
- Casey Anthony at Disney World—Tim praises her for not letting shame stop her from living her best life.
- Tim defends Disney as a fun destination for people of all ages, praising her for getting the most out of it.
- Tim speculates that Casey Anthony would be fun to date because she's a good time.
- Tim argues there's no sexual favor she would refuse given her capacity for extreme actions.
- 4 min
Tim jokingly claims credit for funding Joe Rogan's comedy club, makes a joke about Ukrainian orphans in Austin, then closes by having Tom and Christina plug their podcasts, Tim's Netflix special Sledgehammer, tour dates, and Christina's book pre-order.
5moments
- Tim gave Joe Rogan money to open Mothership because Rogan had no money and called asking for help.
- Tim tells them they've already made it and the only way to fail is to stop doing what they're doing.
- Tim missed Bert Kreischer's movie because he's been working with orphans from Ukraine being shipped to Austin Texas.
- Real money and top-tier real estate are on the East Coast—Palm Beach, the Hamptons, Greenwich, Manhattan—which is why human traffickers like Epstein never operated in LA.
- Tim's new special Sledgehammer comes out Fourth of July on Netflix.
Joe RoganBert KreischerMothershipGhislaine MaxwellJeffrey EpsteinTwo BearsYour Mom's House