Episode 182 · The Ben Avery Era
#182 - Beware the Villas | The Tim Dillon Show
Jan 12, 2020 · 1:15:33 · 165,000 views · 20 segments, 126 moments indexed
Live from a Holiday Inn in Maryland, Tim talks about people who don't get ahead because they live in fear, why a lot of his friends should die in war, the time he was a juror on a murder trial, and his most recent move to the hills.
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- 1 min
Timmy the Trashcan Jingle
#A brief jingle character bit voiced as a talking trashcan begging people not to litter, played as the cold open.
1moment
- Tim introduces himself as Timmy the Trashcan
- 2 min
Live From the Timonium Holiday Inn
#Tim explains he's recording from a Holiday Inn near a truck stop in Timonium, Maryland while playing Magooby's Comedy Club, and riffs on not having enough contempt for his fanbase like truly successful entertainers do.
3moments
- Broadcasting live from the Maryland Holiday Inn in Timonium, a truck stop with a town built around it.
- Tim argues his lack of success stems from not having contempt for his fanbase, unlike successful comedians who visibly despise their audiences.
- Successful people exploit customers shamelessly—like a tow truck driver shooting out tires and then pretending to discover the damage.
- 2 min
Holiday Inn Soap and the Vibe of Timonium
#He describes the harsh industrial soap at the Holiday Inn, compares it to what he imagines prison soap feels like, and riffs on the name "Timonium" sounding like a toxic chemical dumped in a river.
3moments
- Holiday Inn soap is industrial-strength, like prison soap, with no lavender or scent—just raw hand soap from kindergarten painting class in the 90s.
- Tim questions why he'd pay more for a nicer hotel in Baltimore when you could get shot anywhere in the area regardless.
- Timonium, the town 20-25 minutes outside Baltimore, sounds like a toxic chemical dumped in a river that causes birth defects.
- 2 min
Home Depot Aspirants and Bethesda Blood Money
#Riffing off a comic's joke about the local audience, Tim contrasts them with the wealthy Bethesda Country Club crowd and jokes that the audience was disappointed the Iran draft got averted.
5moments
- A comic said he feels like he's performing for people who work at Home Depot; Tim corrects him—these people aspire to work at Home Depot.
- Tim performed at a Bethesda Maryland Country Club for people literally dripping in blood money.
- Beautiful English Tudor and brick castles throughout Bethesda, all built with blood money from the defense industrial complex.
- The people in this area were disappointed when they couldn't go to Iran; half were excited about the draft and getting killed in Tehran.
- When the U.S. averted war with Iran, these people were upset—they actually wanted the conflict to happen.
IranBethesda, MarylandHome DepotCBD oilJosh
- 7 min
We Need Wars to Thin Out the Population
#A sustained bit arguing, with mock sincerity, that many of his friends and directionless people would be better off dying heroically in a war (Iraq, Afghanistan, Iran) than living aimless lives, complete with "flag on the mantel" and recruiter riffs.
10moments
- Tim argues we need wars to thin out the population, suggesting some of his friends should go die in the desert.
- The best version of certain people is as a flag on a mantle inspiring future generations.
- Uncle Gerard now sells CBD instead of being remembered as a war hero—the actual accomplishment matters less than the narrative.
- Tim insists we need a war or population reduction because too many people have no direction or purpose.
- Friends should go to Iraq or Afghanistan and not come back, or come back as a flag—not with PTSD and a pit bull.
- Nobody should join the military shocked about what it really is; you're putting guns in toddlers' faces, not handing out candy.
- Tim pitches an alternate military recruitment pitch: asking high school kids who wants to shoot up the school, then redirecting that talent overseas.
- There are heroic people in the military, but many of Tim's suburban friends need to get killed and never will be.
- The military has done great and not-so-great things, and recruits won't know which they'll end up doing.
- So many people in this country need to be heroes; we should give them a path to heroism through military service and death.
AfghanistanIraqIranmilitary service
- 8 min
Villa Rats and Rule-Followers
#Moving to his new Hollywood Hills-adjacent apartment, he describes the petty rage of "villa" apartment dwellers who call management or police over parking violations, and expands into a theory about rule-followers being motivated by resentment and control rather than talent.
9moments
- Tim just moved to the Hollywood Hills and complains about aggressive towing on his new block.
- Residents of luxury apartments called villas are rats who call management and police constantly out of resentment.
- People who reach villa-level apartments are rule-followers who got good grades and followed every instruction without becoming talented or unique.
- Rule-followers forgot they weren't particularly talented and didn't have interesting perspectives, so they basically died on the vine as paper-pushers.
- Tim describes a certain type of anxious person obsessed with health insurance and Googling diseases they don't have, waiting their whole life for terminal illness.
- Really successful people often don't give a damn about rules, whereas rule-followers are shocked they didn't get further despite checking every box.
- Tim's aunt used horror stories about bankruptcy and car accidents to keep people in line and make them follow the rules.
- Rule-followers brought nothing new or valuable to the table and became indistinguishable from anyone else doing the same job.
- People obsessed with rules love school, college, and health care, but health care doesn't even cover the disasters they've been trained to fear.
- 1 min
Health Care as Organized Crime
#A short capping riff that no matter what health insurance you have, the system is essentially a racket that screws you when something bad actually happens.
1moment
- Tim compares the health care industry to organized crime, saying that no matter what kind of health care you have, something horrendous will happen to you.
- 5 min
An extended, increasingly dark sponsor read for BlueChu (chewable ED medication) built around a repeated "remember those days" refrain that spirals into imagery of heroin addiction and family estrangement.
11moments
- Tim riffs on remembering the days when you could perform adequately for your partner and had a functional penis.
- The fantasy of moving to buy a beautiful home, starting a family, and having hope for a real job that pays.
- Tim catalogs the physical and mental capabilities of youth: waking up hungover without it bothering you, handling booze, smoking without midday cravings.
- The nadir: sucking dick for heroin in a supermarket parking lot.
- BlueChew pitch: first chewable with FDA-approved erectile dysfunction ingredients, works up to twice as fast as pills.
- Tim circles back to the memory of when your parents didn't look at you with pure disgust and fear.
- The lost friendship: you used to go to the beach with Karen, now she won't answer calls after watching you collect cans looking gaunt and pale.
- BlueChew is made in the USA, cheaper than pharmacy prices, ships in discrete packaging directly to your door.
- Tim describes having to defecate outside last week because nobody would let you use their bathroom—they knew you'd tie off heroin in there.
- Final pitch: BlueChew dot-com, promo code Tim—remember those days before you considered eating a cat as a food source.
- The only reason you didn't skin and barbecue the cat is because it would take too much work.
- 1 min
Villa Rats Revisited: Social Security Office Parking Wars
#He returns to the villa/apartment rat theme, imagining a listener who works at a Social Security office and obsesses over parking validation rules as the sum of their existence.
4moments
- These villa residents peer out at visitors and complain about parking, the same people Tim sees living in small apartments.
- Social Security office parking lot rules: reserved spots for GS-14 and above, but open to anyone after 2 p.m.
- Tim reflects on how much of these people's lives revolve around parking validation and following slot assignments correctly.
- Rule-following people are necessary but often surprised they didn't advance further in their careers.
Social SecurityToyota Prius
- 4 min
Boomer Parenting and the School Bus Story
#Tim criticizes boomer-era parenting as self-interested and neglectful, contrasting it with modern helicopter parenting, and tells a story about his dad not knowing which school bus to put him on as a kid.
8moments
- Tim's boomer parents took a vacation from raising him for eighteen years—they were physically present but emotionally absent.
- The boomer generation was driven by self-interest and greed, stuffing their kids with fast food and activities to avoid actually raising them.
- Parents shipped kids off to camps and activities with the implicit message: go get molested and don't bother me, I'm having dinner with Aunt Sue.
- The food Tim ate growing up—McDonald's at two years old—was poison from the jump, courtesy of boomer parenting priorities.
- Tim's father didn't tell him which school to go to on his first day; when asked, he just said get on the bus and figure it out.
- The bus could have been taking Tim anywhere—maybe to Epstein's—and his father had no idea where it actually went or cared to find out.
- Certain successful people are planning their kid's kindergarten while the child is still in the womb, representing every level of parental commitment.
- Tim loves his parents despite their hands-off approach, contrasting it with the obsessive planning of modern wealthy parents.
boomer generationboomer parents
- 4 min
Dad's Late-Life Music Comeback and Giving Up Gracefully
#He recounts his father restarting a musician career in his 60s via local open mics, getting offered a tour, and wisely declining it, which leads into advice that older people chasing new dreams should stop.
8moments
- Tim's dad was a musician when Tim was younger, but gave it up to get a job and provide for his family.
- Dad started playing music again in the local Long Island scene after open mics, and younger musicians invited him to gigs upstate.
- Dad declined further opportunities, saying he's in his mid-60s and needs to go home and watch television with his wife instead.
- Tim tells older people following dreams to stop, because it's over and not the right move.
- Imagining dad telling his wife he's going on the road with the band at 67 and trying to get serious about music now.
- Tim explains that dad had his time with music, probably got some good experiences out of it, but there's no windfall money to chase.
- Don't use Rodney Dangerfield as the one example to justify older people pursuing stand-up comedy.
- There are guys in their 50s at open mics talking about making it—the solution is to go home to your villa and enforce parking rules.
- 4 min
Fear Is Your Friend, Not Something to Conquer
#He argues against the self-help notion of "conquering fear," claiming rational fear is what keeps people employed, housed, and alive, and mocks older comics who never made it but linger at open mics.
6moments
- Tim argues that fear is not meant to be conquered but indulged and befriended.
- Fear is your friend—it's what kept you alive and gave you a home instead of ruining your life.
- Comedians who give speeches about following your dreams on a couch are often dirtbags using that excuse to neglect their own children.
- Tim criticizes parents who do unpaid open mikes instead of providing for their kids' future as immoral and bad people.
- Having a day job while raising kids and pursuing comedy as a hobby is acceptable; doing comedy instead of supporting them financially is not.
- The cultural idea that fear is always bad and must be conquered is wrong—you should lean into it and appreciate it.
- 4 min
Rule-Followers Are Motivated by Control, Not Fear
#He distinguishes rule-followers' motivations (desire for control and to feel superior) from rational fear, comparing them to informants in a tyrannical state, then transitions into having no secret formula to offer aspiring comics.
7moments
- Rule-followers are motivated by desire for control, not fear — they want to look down on others and feel superior.
- Tim describes rule-followers judging a hit-and-run victim for not having health insurance, wanting moral superiority over someone in a coma.
- People who follow rules believe they ascend the social ladder by informing on others, parking violations and minor infractions.
- Rule-followers and informants would be the first to betray neighbors under a tyrannical government for reeducation camps.
- Rational fear, by contrast, motivates hard work — Tim fears disappointing his audience with bad content and releases from a hotel in Timonium, Maryland.
- People without fear seem insane, like children who believe in Santa Claus and don't understand consequences.
- There's no answer to how someone becomes a successful comedian or feature act — either it happens or it doesn't, over two years or five or never.
- 1 min
Advice-Seeking Comics and the Gun Joke
#Riffing on comedians asking him for specific career advice, he jokes darkly that if he gave the honest advice, it would involve them buying a gun to use on themselves.
4moments
- Tim seeks vague advice from respected people on losing weight, getting people to like him, making a million dollars.
- The actual advice would involve purchasing a weapon, because some comedians would be better off not pursuing comedy at all.
- If struggling comics had the dedication or self-awareness needed to succeed, they wouldn't be doing comedy in the first place.
- Tim counts himself among a rare breed who failed everywhere else and found their way into comedy through exhaustion of other options.
- 4 min
Gary Vaynerchuk and the Long Island Medium Hustle
#He defends Gary Vaynerchuk somewhat while mocking his motivational-speaker act, comparing him to psychic hustlers like the Long Island Medium, and brings in his mother's Beanie Baby investment (including the Princess Diana bear) as an example of wasted money.
8moments
- Tim suggests watching Gary Vaynerchuk or picking a motivational speaker to fill you with nothing.
- If you think the Long Island Medium is talking to your dead daughter, you deserve to get your money stolen.
- Paying $300 to sit in a Long Island restaurant while a woman pretends to channel your dead daughter is a transactional con.
- Tim's mother bought Beanie Babies at McDonald's and tried to retire on collecting them.
- After 9/11 it seems weird to be playing with Beanie Babies—nobody really cares.
- The commemorative Princess Diana Beanie Baby was the most popular one his mother had.
- What Gary Vaynerchuk can't tell people is that most of them will never actually enjoy their jobs.
- The world isn't set up for you to wake up on Monday excited—that's not going to happen.
- 7 min
Most People Are Built to Enjoy Life, Not Hustle
#A long rant arguing most people should accept they're built for enjoying life, friends, and hobbies rather than entrepreneurship, contrasting his own performer nature with true hustlers and entrepreneurs, and admitting he doesn't identify as a business person.
10moments
- Most people's happiness comes from family, friends, community, and hobbies, not from monetizing everything.
- Tim distinguishes himself from entrepreneurs—he's a comedian learning business on the fly, not someone who gets excited about growth numbers.
- Gary Vee, Thai Lopez, and similar figures don't determine whether you'll have a business; you either have the internal drive to work or you don't.
- Tim describes the test of an entrepreneur: can you work on Saturday night while everyone else is drunk and having fun?
- At 25, Tim felt he'd done enough partying and backyard hangs; he needed something else or he'd waste his life—but this came from internal realization, not from a guru's plan.
- Tim's friends on a beach right now just want to enjoy life, and that's what people should aspire to.
- Gary Vaynerchuk can't publicly admit that people who succeed are driven by something deeper than love of family—he needs more, and civilization needs people like him.
- Tim was always an entertainer, not a business person, hustler, or deal maker.
- Even making decent money now, Tim doesn't call himself a business person or CEO; he doesn't want people working for him in a boss-employee dynamic, and corporate structure doesn't appeal to him.
- Tim wants to travel doing comedy clubs alone; he'd love a TV show but not if it means being in a writers room or corporate structure that doesn't come naturally to him.
- 6 min
A sponsor read for "Another Bachelor Podcast" describing hosts Nick, Dylan, and Pat and their backstories (schizophrenic parents, Jewish upbringing in Studio City, contentious stepfather), which drifts into Tim riffing on why anyone still watches The Bachelor as humanity declines.
9moments
- Tim says he's never said a bad word about The Bachelor and thinks it's great.
- Host Nick is from La Crosse, Wisconsin, where the Smiley Face Killer operated.
- Tim describes Nick's rough background: both parents diagnosed schizophrenic, raised by his grandmother.
- Dylan, the second host, is Jewish from Studio City with a Trump-loving Vietnam vet father from Virginia backwoods.
- Producer Pat is from Lumbergh, Massachusetts in heroin-ravaged land, raised by his mother and stepfather Jimmy Dell.
- Tim's theory: people obsess over The Bachelor because the Empire is over and we're transitioning to AI dominance.
- The podcast hosts' tragic backstories inform their comedic perspectives on the show.
- Pat is probably 50 years old and likely on the edge of killing himself, which is why people should listen to his show.
- Men are idiots and also watch The Bachelor, so if you watch it, check out Another Bachelor Podcast.
- 2 min
Hitting Bottom Selling Mortgages on Long Island
#Tim describes bottoming out at 25 selling subprime mortgages in a dying post-crash office on Long Island, drinking heavily and living rent-free after defaulting on a house he bought at 22.
5moments
- Tim had to bottom out first, which he connects to Gary Vee's philosophy about failing enough.
- Tim hit a wall at 25: drinking every night while working a job that no longer exists.
- The job was selling mortgages in 2009, right after the financial crisis—insane timing.
- The office was decrepit, windowless, on Long Island with fruit flies and ceiling leaks.
- All the mortgage guys had vanished; their Porsches and Maseratis were repossessed or gone.
- 12 min
Jury Duty on a Murder-Torture-Rape Trial
#A long story about getting selected for jury duty on a gruesome trial as a directionless 25-year-old with a suspended license, outsmarting the defense attorney's questioning, and how the experience became the catalyst for him quitting his job and starting comedy that fall.
12moments
- Tim receives jury summons and immediately senses it might be a pivotal event
- Directionless 25-year-old with his friend Ryan on Long Island, stealing from parents to eat at corporate steakhouses
- Tim bought a house at 22, stopped making mortgage payments when it dropped 50% in value
- News vans outside the courthouse signal this isn't a typical Wendy's slip-and-fall case
- The trial is for murder, torture, and rape—Tim is immediately excited by the gravity of it
- Defense team selected Tim as a juror, reading his face as someone who understands extenuating circumstances
- Tim's driver's license was suspended over 20 times; he couldn't legally drive to the courthouse
- Prosecutor asks if Tim hates police due to suspended license; he says he hates himself for being irresponsible
- Defense attorney in Miss Frizzle outfit asks if Tim can be impartial hearing murder, torture, rape—he answers words mean nothing
- The trial was an intense meditation on mortality that made Tim realize he couldn't sell mortgages anymore
- Tim started comedy in late August that year, after spending one more summer drinking and nearly dying in boating accidents
- Sometimes you have to get being a loser out of your system before you can stop being one
Long IslandGary VaynerchukVince's clam barRyan
- 1 min
Tim thanks Josh for helping record the episode and lets him plug his show "Gin and Jokes" at Joe Squared in Baltimore and his podcast "The Digression Session" with Omar.
2moments
- Tim asks Josh to plug his social media and local show details.
- Matt Josh and Omar describe their podcast, The Digression Session.
The Digression SessionGin and Jokes