Episode 261 · The Ben Avery Era
#261 - Please, Die Alone | The Tim Dillon Show
Jul 18, 2021 · 1:24:16 · 399,000 views · 26 segments, 174 moments indexed
Joining us from New York City is the comedian Tim began comedy with, Kunal C. Arora, to discuss their early beginnings in Long Island, Call Her Daddy and Armchair Expert podcast deals, people moving back in with their parents, and why New…
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- 2 min
Call Her Daddy's $60 Million Deal and the Podcast Money Bubble
#Tim and guest discuss Call Her Daddy's reported $60 million deal, question whether Barstool merch drives real profit, and joke that podcast money has gotten as silly as bitcoin hype years ago, with Spotify reportedly pulling back on big deals except for stars like Rogan.
5moments
- Tim claims Call Her Daddy won't make back its $60 million deal—nowhere close to $6 million even.
- He tried listening to an episode and turned it off after four seconds.
- Tim argues podcast money valuations have gotten silly, comparing it to the Bitcoin bubble from five or six years ago.
- Spotify is pulling back hard; they're solid on Rogan but apparently unhappy with Bill Simmons' Ringer deal despite the $100 million investment.
- The money might not even be real—just Spotify credits that function like loans or IOUs.
Call Her DaddySpotifyBarstoolThe Ringer
- 2 min
Spotify's Fake IOUs and the Call Your Daddy Alternate Show Pitch
#They riff on Spotify dangling fake deals and shady 'agents' who lie about offers, then invent a bit where 'Call Her Daddy' is reimagined as 'Call Your Daddy,' a show where a woman confesses sexual details to her actual father until he can't take it anymore.
5moments
- Spotify never actually offered them money — the agent lies and says a deal might come through
- Streaming platforms make up fake companies and dangling offers to make podcasters think big deals are coming
- Tim describes the absurdity of being told about massive offers like $250 million that will never materialize
- Moving to Spotify exclusive meant Rogan couldn't be found anywhere else
- Tim describes the bit where her father picks up increasingly dejected as she continues calling episode after episode
- 2 min
Dax Shepard's Armchair Expert and the $60 Million Therapist Act
#Tim mocks Dax Shepard's Armchair Expert podcast reportedly getting $60 million, questioning why a guy known mainly for marrying Kristen Bell is now positioned as a therapist to already-rich celebrities.
8moments
- Tim recounts a Cancun story where someone listens to a podcast episode and then shoots himself, ending the call with a gunshot sound.
- Spotify's exclusive podcast deals include massive contracts—they threaten to kill people if the show appears anywhere else.
- The Ringer, Joe Rogan, and Call Her Daddy all got major Spotify deals; Dax Shepard's Armchair Expert supposedly landed $60 million.
- Tim questions whether Dax Shepard's main claim to fame is being married to Kristen Bell rather than his podcast.
- Armchair Expert is basically Dax acting as a therapist to rich celebrities like Paul Rudd and Seth Rogen.
- Tim's skepticism: why would wealthy, famous people need someone to tell them they're rich—that's all he can do from a nice armchair.
- Concern that Dax is pretending to be an expert and getting paid $60 million while actual experts have nothing.
- The podcast's official description claims it celebrates the messiness of being human—Tim considers jumping out the window.
Dax ShepardArmchair ExpertCall Her DaddySpotifyKristen Bell
- 4 min
Canal Aurora recalls meeting Tim in 2010 at a Long Island coffee shop/tattoo parlor open mic called Wild Child, including memories of bad sets, tattoo cover-up consultations, and a friend named Scott who gave a fake name.
9moments
- Canal Aurora introduces himself and provides his social media handles across multiple platforms.
- Tim met Canal Aurora at open mics in late 2010, where Tim was doing his first comedy set ever at a tattoo parlor slash coffee shop on Long Island.
- The tattoo shop's needle would buzz loudly whenever Tim bombed on stage during his set.
- The tattoo shop specialized in coverup work, particularly turning ex-girlfriend names into R.I.P. memorials with dates like 9/11.
- Tattoo artists would constantly warn customers that the decision was permanent, which felt eerie to hear while doing stand-up comedy.
- Canal Aurora was typing on a netbook during Tim's set and would occasionally react with a dismissive "huh" when something was funny.
- Another comedian introduced himself as "Michael" the first time Tim met him, even though Tim knew he'd know this guy for the rest of his life.
- Tim started doing a thing called Trip Sunday where he'd take two comics and hit three open mics in one day across 100 miles of driving.
- The rotating crew for Trip Sunday would include Canal Aurora, Dennis, and others, switching around based on who was booked or available.
- 4 min
They recount the legendary 'Trip Sunday' story of doing three open mics in one day, culminating in a bizarre real-life confrontation between two competing Rodney Dangerfield impersonators at a Huntington club, one of whom had just had a heart attack.
8moments
- Tim recalls the night he and his guest decided they had to move into New York City after endless drives to Long Island comedy mics.
- They bombed at the hipster mic and the black room, then headed to a second-floor club called Chesterfields in Huntington.
- The club claimed Eddie Murphy started there, though nobody knew what that actually meant—possibly just that he took a bus that passed by.
- Tim notes the people saying this were the most racist in America, taking pride in Eddie Murphy's accomplishments while having racial slurs scrawled on the glass.
- A Rodney Dangerfield impersonator got up on stage to perform Dangerfield's own material at an open mic.
- Someone suddenly yelled from offstage, and when they looked over, another Rodney Dangerfield impersonator in suit and red tie was standing by the door.
- The second impersonator yelled "You stole my act" in complete earnestness—genuinely upset, not joking at all.
- The second impersonator continued his complaint from offstage: "Just because I had a heart attack, you think you can do my act."
- 4 min
Canal recalls Tim announcing he was moving to Manhattan after the Rodney incident, and they discuss how staying in Long Island lets you keep a normal job/identity, while moving to NYC forces comedy to become the organizing principle of your life.
10moments
- Tim whispers that he's moving to the city next week.
- Rodney Dangerfield had legitimately suffered a heart attack and was in cardiac recovery.
- Tim couldn't barely tell it was Rodney in the impersonation—doing a Dangerfield bit is a young man's game.
- Tim lived in an apartment in the East Village, in Alphabet City, and was the first among the group to actually move.
- He moved soon after Tim because hanging out with him made him realize the city setup worked better.
- Open mics on Long Island are easy because you drive, park, do your set, and leave—not like the subway rides and bar-to-bar grind in the city.
- When you make the sacrifice to move to New York City, you're taking on a different identity.
- Tim argues it's not about money—being a real comedian means it has to be the organizing principle of your life.
- To be a comedian, the choice to pursue it has to shape your decisions and life path.
- They knew in Long Island what they didn't want to be, which was a great thing about starting there.
- 3 min
They talk about revisiting bad Long Island diners, going to Dar Williams folk concerts together, and Tim's annoyance when she'd pad her sets with poets and neighborhood speakers instead of just performing.
4moments
- Tim says Long Island diners used to be better but now they're terrible, and he's glad his journey was out of there.
- He mentions possibly moving back to Long Island and getting addicted to pills.
- Tim got upset when Dar Williams started bringing out other performers—a poet, neighbors talking about gardening and local politics.
- The complaint: when you're the headliner, do your full set instead of using the show as a platform for random guests and causes.
Dar WilliamsLong Island
- 3 min
A sponsor read for Sheath Underwear spirals into an extended dark bit defending the (fictional) owner Robert, who is being charged with war crimes in Iraq for shooting a pregnant woman and allegedly setting her on fire.
7moments
- Tim endorses Sheath Underwear and its owner Robert Patreon, who is being charged with war crimes at The Hague.
- Tim claims the pregnant woman shot by Patreon did have a bomb and that he acted appropriately.
- Tim emphasizes the importance of supporting Robert during his war crimes trial, noting he shot a pregnant woman in Iraq as a last resort.
- The woman didn't even die from the stomach shot—she lost the baby, which Tim notes is what people don't realize.
- Accusers claim a man matching Patreon's description doused the woman with kerosene and lit her on fire after shooting her, which Tim does not believe has been proven.
- Patreon was dishonorably discharged for going AWOL and not respecting the chain of command while butchering women and children.
- Tim argues Patreon was doing what needed to be done to secure his brothers' safety and fight for the nation's interests.
- 3 min
A BetterHelp ad turns into an elaborate fantasy monologue imagining small-town America (loose meat sandwiches, car dealerships, beach clubs) transformed because 'you went to BetterHelp,' riffing on Selena Gomez's 'Lose You to Love Me.'
4moments
- Tim describes the Norman Rockwell fantasy of BetterHelp: dancing under stars, becoming a respected community elder, getting the corner office.
- Everyone at the local tavern greets you with respect after you've unloaded your problems to BetterHelp.
- Car dealerships stop trying to con you and actually help you get a good vehicle because you went to BetterHelp.
- The ice cream truck always has what you want in stock, and people refuse your money because of your improved mental health from BetterHelp.
- 6 min
Tim and Canal discuss comedians leaving NYC during the pandemic to reconnect with family, thinking about death and comorbidities, and Tim's dark joke that his father and stepmother would rather he die anywhere but at their house.
7moments
- Tim stayed in New York during the entire pandemic while many comics fled home.
- Comics who left to reconnect with family and their original psychiatrists needed that self-esteem hit.
- The pandemic forced a reckoning with mortality in a way people had never considered before.
- Tim remembers the anxiety of hearing about comorbidities and realizing he was at risk—smoker, overweight, 36 years old.
- Kenny Ortega, a big funny comic who could kill in any room, died from COVID.
- Tim has no home to go back to, unlike many others, and couldn't have relocated anyway.
- His father and stepmother would have explicitly told him not to come home to die—to die alone instead.
BetterHelpKenny OrtegaSelena GomezTaylor Swift
- 3 min
Tim talks about having no family home to retreat to during the pandemic, dark jokes about dying alone with a young hookup, and the idea that some pandemic restaurant closures were deserved.
7moments
- Tim describes dark pandemic thoughts about dying alone without anyone to sit by his bedside.
- When he asks guys in their early twenties to keep him company while dying, they immediately ask if they're in his will.
- Career as a measure of worth flips depending on circumstances — first thing you want when there are no opportunities, last thing when you're actually dying.
- His 24-year-old opener complained that no one's fucking anymore and bars closed, claiming he'd die alone.
- Restaurants closing during COVID gave shitty burger joints an excuse to shut down forever.
- Tim celebrates when bad restaurants die — he didn't need to eat at places with horrible brunch anyway.
- He hopes struggling restaurant owners realized their lives shouldn't be dedicated to sriracha aioli and stay gone.
- 3 min
They discuss how frightening Times Square felt late at night compared to the rest of NYC, and how the city's post-pandemic bounce-back (and more subway riders) has actually made homeless people less aggressive since more money is trickling down.
6moments
- Tim describes Times Square late at night as haunting and genuinely frightening.
- The fear in Times Square is visceral—worrying about being attacked, hearing a syringe drop.
- Living through the pandemic taught him to come back harder, abandon comfort, and embrace the city's toughness.
- More foot traffic on subways means homeless people get more money, making them less aggressive and the city safer.
- Growing up on Long Island and living in New York for years, he no longer feels at home there.
- He's become softer—the old New York attitude of not caring, of glamorizing street violence, no longer makes sense to him.
- 2 min
Tim says he no longer wants to be 'New York tough' but 'Midwest considerate,' recalling politeness in Chicago, and mocks New Yorkers who travel to places like New Orleans and complain they can't get a decent slice or turkey sandwich instead of appreciating local food like Creole cuisine.
5moments
- Tim says he'd rather be Midwest considerate than New York tough.
- A random woman in Chicago offered unsolicited directions when he asked a friend where to find a Chase ATM, nearly prompting him to snap at her.
- Tim argues that cities shake you out of your comfort zone and drive innovation, but there's value in not losing yourself in the process.
- New Yorkers used to seem worldly to him, but now they just compare everywhere else to New York.
- Tim points out that Creole cuisine—a fusion of French, Caribbean, and Haitian influences—doesn't exist anywhere else in America, yet New Yorkers ignore it to complain about sandwiches.
- 3 min
Canal describes finally finding his footing in LA after feeling something was missing in NYC, and Tim recounts realizing Canal was 'done with Austin' the moment he started bragging about it, cementing Tim's own disdain for the city.
6moments
- Tim has surrendered to Los Angeles for good.
- He wasn't sure he was done with Austin when he first moved out there.
- Tim figured things out in a garage with someone's help.
- As he gets older, he thinks more about planting a flag and creating some type of home.
- It's not Austin, Texas—he tried it for four months.
- When Tim heard Ben phrase Austin's advantages in comparison to New York, he knew the move was done.
Los AngelesAustinNew YorkCafé du Monde
- 2 min
Tim delivers an extended takedown of Austin as a mediocre place for mediocre people, then pivots into reflecting that the pandemic taught him life is short and he's finally stopped over-identifying his self-worth with how a comedy set goes.
7moments
- Tim on Austin: it's a C-list town where the dullest people go, not the best and brightest.
- He wishes nothing but pain for everyone in Austin, though he'll still work Joe Rogan's club.
- Tim realizes during the pandemic that life is short and you spend most of it bullshitting yourself and others.
- The struggle for comics: fighting insecurity and self-worth, building yourself up only to knock yourself down again.
- Comics wake up with different feelings every day—one good set makes you feel like a king, then you compare it to better past performances and get unhappy.
- Tim's happiness was too tied to how his sets went, a trap he's realized he's too old for now.
- As you get older, it stops mattering how the sets go—you just walk away and don't care.
- 4 min
Back-to-back ad reads for ShipStation's shipping logistics discounts and Bespoke Post's surprise subscription boxes, with Tim repeatedly insisting he only wants boxes containing knives and no grooming products.
3moments
- Tim asks if the listener likes knives, pivoting from the Bespoke Post grooming box.
- He doesn't want summer styles or grooming goods—just knives, repeatedly and exclusively.
- Tim tells Bespoke Post not to waste time sending him bottle openers, gloves, or grooming items.
- 4 min
Back-to-back ad reads for ShipStation's shipping logistics discounts and Bespoke Post's surprise subscription boxes, with Tim repeatedly insisting he only wants boxes containing knives and no grooming products.
3moments
- Tim asks if the listener likes knives, pivoting from the Bespoke Post grooming box.
- He doesn't want summer styles or grooming goods—just knives, repeatedly and exclusively.
- Tim tells Bespoke Post not to waste time sending him bottle openers, gloves, or grooming items.
- 5 min
Tim and Canal reflect on their early friendship, Canal's mom's cooking, being long-island outsiders looked down on in the city, and how differently immigrant families react to their kids choosing comedy as a career.
9moments
- Tim recalls the guest being the first friend he had in comedy who genuinely loved it.
- Memories of the guest's mother making Indian food at her house during their early comedy days.
- Tim and the guest were Long Island guys who looked down upon by New York City comedians in their mid-20s.
- The guest chose comedy as his life in his mid-20s and has now moved beyond that era.
- The guest explains he's never loved anything except comedy.
- Guest describes watching Kevin Nealon on SNL and initially thinking he was trying to get fired from his news job before realizing it was a comedy show.
- Tim asks why the immigrant story doesn't usually involve comedy, since parents would oppose it.
- White parents don't care about their children's careers the way immigrant parents do, allowing comedians to pursue the path.
- Tim's theory: immigrant parents either beat their kids hard enough to discourage comedy or didn't beat them enough, which explains whether they pursue it or not.
Saturday Night LiveKevin NealonEddie MurphyKevin James
- 4 min
They discuss the lesson that you don't need everyone's approval — not family, not audience members who aren't your crowd — using the analogy of a subway singer some people loved and others wanted thrown off the train.
6moments
- You don't have to win everyone over — that's the lesson Tim keeps trying to drill down on, watching people obsess over universal approval from family, friends, community.
- Tim notes there are always people on his show who shouldn't be there, audience members it's not made for, and that's completely fine.
- He doesn't care who likes him outside the people who already think he's funny — he'll work his ass off for those people, but the rest can go watch something else.
- Tim admits that early in his career he desperately wanted people to understand his journey and validate his existence as a performer, which he now sees as a colossal waste of time.
- When he first started, Tim believed his job was to inflict himself on people relentlessly until they finally gave in and agreed with him.
- A subway singer doing an awful, off-key performance taught Tim the real lesson: some people enjoy it, some people hate it, and that's just how it goes.
- 3 min
Canal and Tim compare their outsider status as an Indian comic and a gay comic within their respective communities, and argue that real progress is an Indian or gay comedian headlining in places like central Pennsylvania or Long Island because they're funny, not because of quota-hiring.
7moments
- Tim's audience isn't Indian people, and he talks himself out of Indian gigs.
- Neither Tim nor his guest are the stars of their respective communities—Indian and gay people, respectively.
- They're meant to look at their communities differently, providing an angle that challenges stereotypes.
- Entertainment industry gatekeepers want to fill a protocol rather than genuinely value diverse perspectives.
- An Indian comic headlining clubs in central Pennsylvania matters more than token hiring at major channels.
- A small-town venue hiring a funny Indian comedian because he's genuinely entertaining shifts everything.
- Tim encounters people surprised that a Hindi comic can be this funny, and finds the reaction baffling.
- 4 min
Tim explains how coming out of the closet taught him to stop needing approval, and how he's applied that same 'f*** them' philosophy to moving to LA, wearing a wig in a video, or doing Logan Paul's podcast despite judgment.
9moments
- Tim wrestles with whether he could live outside New York City, noting other comics moved to LA.
- So much of life revolves around a shitty career, even when it's a good one and you've done great things in it.
- Quoting Kathy Griffin: the only award in comedy is to say you're still doing it.
- A lot of people now aren't standing in the rain—they think they're in it but it's just a gray day.
- Tim saw an old show flyer from seven years ago and realized a lot of those comics quit and moved into writing.
- A gig writing bits for radio once a month felt like a day job, even for $150—he'd dread the entire time.
- The biggest thing Tim figured out: he didn't need the people he thought he needed.
- When Tim came out of the closet, he realized his friends might not like him anymore, but who cares.
- Every decision—moving to LA, wearing a wig in a video, going on Logan Paul's podcast—Tim approaches with the same attitude: people might judge, but fuck them.
- 4 min
Tim and Canal mock producer Ben's entitled behavior (expecting his hands dried, complaining about eating lobster in the Hamptons) and joke about sending him back to work at Petco/Urban Pet, where he originally worked, as a reality-check vacation.
10moments
- Tim describes his producer as entitled and admits he's made him a monster.
- The producer demanded Tim dry his wet hands while eating lobster bisque at a restaurant.
- Tim met his producer while he was working at Urban Pet, a boutique LA pet store selling mostly hairless cats.
- Tim suggests making the producer's vacation be two weeks working at Petco to keep him grounded.
- The producer's actual day-to-day life is already a vacation, but he complains constantly to his wife about it.
- Tim has taken this kid all over the world, including to the Bitcoin conference.
- Tim compares podcasting to collecting action figures, unsure if it's actually a real career.
- Tim jokes that they actually charge people money to do the podcast instead of paying them.
- Any revenue from the show goes directly to Dax Shepard because Spotify doesn't have the money to pay everyone else.
- Tim mentions having a best friend named Trevor from back home, though he clarifies Trevor wasn't his closest friend.
Dax ShepardSpotifyUrban PetPetco
- 4 min
A reflective conversation about whether devoting life to comedy at the expense of health was worth it, the universal ache of wondering 'what if,' and mention of their friend Trevor who died of a pill overdose, contrasted with another friend Chris who found an idyllic life in Italy.
10moments
- Friend who backpacked through Italy, met a girl on a train, moved to Milan, and now has a wife and kids there.
- Tim casually mentions his friend Trevor is dead, possibly from an overdose, then pivots back to Italy.
- Tim jokes that the friend in Italy might secretly wish he had a podcast instead of his family.
- Tim imagines the friend resenting his wife and child for keeping him from talking to Joe Rogan about Bigfoot.
- Every person has something that gnaws at them, something dark that haunts quiet moments.
- Humans know life ends, which makes us fundamentally different from most animals who live moment to moment.
- We make choices in life knowing they'll produce both expected and unexpected results, creating natural regret.
- Tim describes the mind's instinct to wonder "what if I'd made a different choice" even when the actual choice worked out great.
- Entertaining those counterfactual regrets feels like flirting with depression to Tim.
- Tim's approach now: acknowledge what happened, accept it, and move forward without dwelling in that mental space.
- 4 min
Tim talks about quitting a pandemic-era game show project just because he didn't want to keep doing it, and the philosophy of prioritizing what makes you feel alive over hitting career milestones, even referencing Ghislaine Maxwell as an extreme example of 'truly living.'
10moments
- Tim wonders if he should have devoted more life to mental and physical well-being instead of the entertainment industry.
- Many of the most successful people in the business are criminally insane and can swim in money but it doesn't save them.
- Tim questions what the cost is of the cool things he loves doing.
- He jokes that heroin would eliminate the mental feeling of wondering about the cost of his career.
- People commonly ask themselves what else they could be doing, but if Tim wanted to do something else he would.
- During the pandemic he created a game show, shot episodes with comics, but didn't want to keep doing it despite people saying it was a good idea.
- You only have a certain amount of time, so do the things you want to do because it's over that quick.
- Throwing rocks from a roof was one of the funniest moments and he laughed harder than he ever had as a child.
- Questionable characters like Jeffrey Epstein and Ghislaine Maxwell truly lived, even though they did terrible things.
- Tim's philosophy: make yourself as happy as possible without doing it at someone else's expense, but just do that.
- 4 min
Canal plugs his comedy album 'Draw Four' and social handles, then Tim vents about being harassed online for stating a neutral opinion on vaccines, arguing people need a moral side to pick to feel their lives have meaning.
6moments
- Canal's album is called 'Draw Four,' based on the Uno card.
- Tim says he's vaccinated and doesn't care what others do, but people got angry anyway.
- His stated non-opinion upsets people because they need to pick a side in a good-versus-evil narrative to give their lives meaning.
- Tim dismisses claims he's being paid by Pfizer, noting they wouldn't hire someone who questions 9/11 to promote vaccines.
- He lays out the actual stakes without judgment: some unvaccinated young people are fine, older people are mixed, some vaccinated people get sick, some unvaccinated people die from COVID.
- The real question is why either side cares so intensely about what their vaccinated or unvaccinated neighbor does.
PfizerCanal Aurora
- 1 min
A fake Pfizer sponsorship bit imagines annual booster shots marketed like Netflix subscriptions with side effects like Bell's palsy, before Tim thanks Canal Aurora and closes out the episode.
3moments
- Tim predicts annual booster shots will become a subscription service like Hulu and Netflix, stacked into monthly expenses.
- He catalogs potential vaccine side effects—Bell's palsy, death, taste loss, tongue paralysis—then notes the Pfizer CEO will end up in a really nice house regardless.
- Tim jokes that Dax Shepard will have the Pfizer CEO on Armchair Expert to explain why it's fine that people can't chew anymore.