Episode 322 · Post-Ben
Bobby Kelly | The Tim Dillon Show #322
with Bobby Kelly
Nov 6, 2022 · 1:32:12 · 304,000 views · 25 segments, 174 moments indexed
Tim Dillon is joined in-studio by Bobby Kelly to discuss comedy, real estate, food addiction, LA hookers, & much more
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- 4 min
Long Island vs. Shelter Island: The Party Circuit
#Tim and Bobby Kelly discuss visiting each other's homes, Louis CK's Shelter Island parties, the absurd cost of renting helicopters to Hamptons parties, and Aaron and Christine flexing their helicopter arrival.
9moments
- Tim identifies the problem with Long Island: the Highway of Death.
- Louis C.K. invited Tim to a party on Shelter Island with a yacht, but Tim couldn't make the six-hour drive with a baby.
- Tim would consider going to Shelter Island in January when it's snowing and nobody else is there, but not on a Saturday during summer.
- Aaron rented a helicopter to get to the party, though it didn't land at the house.
- Tim notes Aaron has to tell everyone he took a helicopter since it didn't actually make a difference in how he arrived.
- A helicopter rental from New York City to the Hamptons costs around fifteen hundred bucks.
- Tim had a Mr. Softee truck show up at his Long Island party.
- Planning a party on Long Island gave Tim a feeling of deep sadness and depression.
- The party on Long Island was supposed to depress people.
- 1 min
Louis CK's Star-Studded Thanksgiving Party
#Tim recalls attending one of Louis CK's Thanksgiving parties packed with Oscar winners and how depressing it felt watching Louis's status decline.
2moments
- Louis CK was at the party, hanging out with Luis Gomez and seeming to enjoy himself, which struck Tim as bittersweet.
- Tim went to Louis CK's house once and he made him a steak.
- 2 min
Trying (and Failing) to Remember Famous Party Guests
#Tim and Bobby struggle to recall the names of actors from Scarface, The Exorcist, and Boogie Nights who were at Louis's party, riffing on getting older and losing memory.
7moments
- Tim tries to recall Oscar winners at a party, including the actor from Scarface who got thrown out of a helicopter.
- Joan Rivers and her daughter showed up; the daughter was playing with someone's kid.
- The mother from The Exorcist was at the party.
- Tim can't remember the actor from Boogie Nights, the one who tried to kiss Mark Wahlberg.
- Tim admits he doesn't know anyone at that celebrity level, though big actors text him fan messages.
- Bobby suggests Tim should have bought property in Westchester to attract famous guests instead of living by the beach.
- Tim argues Westchester is better than where he lives, citing proximity and accessibility despite Bobby's dismissal of it as hack.
Rosebud BakerChris PennMark WahlbergRyan ReynoldsScarfaceThe ExorcistHoward SternJerry Seinfeld+1 more
- 6 min
The Great Lake vs. Ocean Debate, Long Island vs. Westchester
#A long back-and-forth argument about whether lakes or oceans are better (sharks, hurricanes, drunk lake people), followed by dueling claims that Westchester and Long Island are each the superior place to live, ending in a shared fantasy about dying of AIDS to escape podcasting.
10moments
- Tim doesn't like the ocean and prefers lakes, though he admits he's only 10-12 minutes from a beach.
- Lakes are for men; oceans are for rich elites and the whitest of white people.
- Lakes don't have hurricanes or tsunamis like oceans do—when God sneezes on the ocean, your house gets wiped away.
- An app tracks great white sharks off Long Island, but they don't bother people.
- A great white shark placed in a lake would be disgusted and die immediately since they can't survive fresh water.
- Lakes like ones in Westchester with party coves are full of drunks on boats and drunk girls—garbage people and garbage lakes.
- The Northeast has civilized lakes where you can kayak, swim off a dock, see foliage, and ice skate in winter.
- Tim wants his guest to give the ocean another chance—you can't open your eyes in saltwater, but lakes let you see.
- Squam Lake in New Hampshire, where On Golden Pond was filmed, is the kind of beautiful, quiet lake he's talking about.
- Tim jokes about having AIDS and dying in six months, saying it would be great to die as a straight man and never do anything gay—but even HBO wouldn't give him a special for it.
Squam LakeLake AustinHoward SternOn Golden PondDonkey Kong Country
- 5 min
Landing in LA: The Sadness and the Androgynous Cowboys
#Tim describes the depressing energy of Los Angeles, the aggressive/dismissive vibe from locals, and a bizarre restaurant encounter with androgynous, Johnny Depp-looking couples at the Ivy.
7moments
- Tim describes the sadness that hits him when landing in LA, even just getting an Uber.
- The aggressive, dismissive energy from men in his hotel — not friendly, isolating and lonely.
- People who stayed in LA developed hardened exteriors as the city got worse, becoming less fun.
- Hotel worker jaded after dealing with homeless people defecating outside, cops unwilling to help.
- LA fashion obsession compared to New York regularity — people looking like they stepped out of magazines.
- Androgynous cowboys in shiny rings and bracelets appearing at the Ivy — attractive but in an odd, unsettling way.
- Tim explains LA residents' entire existence revolves around dressing like Johnny Depp and being seen at restaurants at 5:30 PM.
- 9 min
Austin's Comedy Boom and the Joe Rogan Effect
#They discuss Austin's rise as a comedy hub thanks to Joe Rogan, his club expansion, the Vulcan comedy club experience, skyrocketing Austin housing costs, and fantasize about moving into Rogan's studio/home.
10moments
- Tim describes the Vulcan comedy club in Austin as amazing, with a young crowd of funny comics and off-the-chain atmosphere that reminds him of the old Cellar in New York.
- Joe Rogan's early prediction about Austin becoming a comedy hub was right, though the timeline was slower than expected, and his club opening in a few months will have two clubs inside it.
- Tim pushes back on characterizing Austin as the new New York or LA, calling it simply a growing small college town.
- Hotels in Austin are outrageously expensive at $400 a night, driven up by Elon Musk and Joe Rogan telling people it's the place to be.
- The Austin housing market recently cooled after years of insane bidding wars where houses received 30-40 offers and sold 30-40 percent above ask.
- Tim proposes that he, Joey Diaz, and others should move into Joe Rogan's house because it's big enough, or sleep in the sauna at his studio.
- Joe Rogan's studio is overwhelming with all its tech, deprivation tank, sauna, and gym, and has always been deliberately nondescript from the outside.
- Tim is considering selling his Long Island house and moving to Austin when Joe's club opens, which prompts advice about buying property near a lake instead.
- Tim previously trashed New Orleans food as bad gumbo, but later returned with Nick di Paolo and discovered it actually had some of the best food he'd eaten.
- Tim's mortgage in Texas is incredibly cheap at $2,900 a month, making him seriously consider relocating and staying at the property.
Joe RoganThe VulcanAustinNew OrleansElon MuskRay DonovanJoey DiazNick de Paulo
- 1 min
Ending the Long Island vs. Austin War, and LA's Food Redemption
#Tim declares a truce in his running joke feud with Austin, comparing it to Ukraine and Russia, and credits LA for having genuinely great food now.
4moments
- Tim ends his public war with Austin, arguing that like all wars, it eventually has to end.
- LA sucks, but Tim concedes the city has genuinely great food now and deserves credit for it.
- His priorities visiting LA have shifted over time: first looking for hookers, then food, now podcasts.
- Tim notes his descending life trajectory—hookers, food, podcasts—getting sadder at each stage.
- 2 min
Tim reads a sponsored segment for Kamakoto Japanese steel knives, joking about how a nice knife set can distract dinner guests from controversial things you've said.
4moments
- Tim explains Kamakoto makes knives, which everybody needs for the holidays.
- The wooden box makes Kamakoto knives a great gift and helps with storage.
- Opening an expensive knife box at dinner makes people forget about whatever controversial things you said.
- Tim says bringing out knives to show people is almost as cool as bringing out a gun.
Kamakoto
- 4 min
LA Weekly Hookers and Getting Robbed by a Pimp
#Tim tells stories about hiring sex workers via LA Weekly ads in the past, comparing scams in LA versus New York, and recounts a tense encounter where a pimp with a gun confronted him, ending in a bizarre forced dance/masturbation scene.
9moments
- Tim used to find hookers through the LA Weekly classifieds in the back, where the pictures never matched reality.
- The girl in the ad would be blonde, but a Spanish woman in her 50s with zits would show up instead.
- LA sex workers were consistently worse than New York's, where there was at least some kind of code that got you what you paid for.
- Tim showed up to a hotel where the worker said they couldn't touch each other, just get naked while he masturbated—effectively the same as being alone in his room.
- Tim describes what sex work in Austin would probably be like: a woman who smells like brisket with burnt brisket ends as pasties, bikey tattoos, ashy elbows, and green hair.
- Tim almost got shot when a pimp came to his hotel room with a gun after Tim complained about being sent the wrong girl.
- After Tim complained to the service, they sent the girl back up—and her attitude was terrible, so was his.
- Tim made her dance while he masturbated in front of her because he wanted to get his money's worth after the bad service.
- The whole experience was the worst: she was doing angry pissed-off dancing while he was angry jerking off.
- 3 min
Getting Sober from Sex Addiction
#Tim discusses his history of addictions moving from food to drugs to sex, hitting a low point that nearly cost him his relationship, and how Colin Quinn's advice helped him get sober and save his marriage.
6moments
- Tim says sex addiction was the worst of his cycle through food, drugs, and compulsive behavior.
- After getting sober from drugs, sex became an immediate compulsion—hunting it down constantly, checking hotel Yellow Pages for massage parlors.
- His wife gave him an ultimatum when the relationship nearly fell apart from his behavior.
- Colin Quinn's advice to try changing for a year saved his relationship and his life—the only good counsel among friends telling him to quit.
- Tim compares sex and food addiction: sex you can theoretically eliminate, but food is the worst because you can't get rid of it entirely and still survive.
- He jokes that he never got jerked off to El Pollo Loco at 11 p.m., but eating there is a separate problem.
- 8 min
Food Addiction: Ordering Three Things and Never Being Full
#Tim details his ongoing struggle with food addiction, his grandmother's advice about ordering too much at McDonald's, America's absurd portion sizes and appetizer culture, and finally deciding to lose weight after years of physical decline.
13moments
- Food feels as addictive as sex, and Tim thinks few people understand that quality.
- Even fat people often don't view eating as an addiction—they just eat and get lazy about it.
- Tim still orders multiple items at restaurants despite knowing better, like ordering two things at lunch.
- His grandmother once asked why he ordered three things at McDonald's when he's only one person.
- Tim used to order three large fries to reach the point of fullness, since one large fry was never enough.
- America's approach to restaurant portions—appetizer, entrée, dessert—is unique compared to other countries.
- A single entrée at Red Lobster contains about 2,000 calories, which is nearly a full day's intake.
- At the Cheesecake Factory, Tim and friends would order appetizers like chicken wings, quesadillas, and stuffed mushroom bites before the main course.
- At a Vegas steakhouse, Tim had a shellfish tower, carpaccio, lobster ravioli, chateaubriand, sides, and desserts in one sitting.
- Tim decided he was done being fat after feeling like an anaconda that had just swallowed a capybara and couldn't move anymore.
- His obesity caused heartburn every night, swollen feet, knee pain, and he could hear his labored breathing on podcasts.
- After quitting alcohol and drugs, Tim had to give up food as his first addiction.
- His new hour, produced and directed by Louis C.K., focuses extensively on food addiction and his multiple weight-loss attempts.
Louiefood addictionCheesecake FactoryMcDonald'sRed LobsterSam TalentLily Tomlin
- 7 min
Making the New Hour with Louis CK: The Elvis '68 Setup
#Tim describes his new food-addiction-themed hour filmed in Tampa with Louis CK directing, designing the stage after Elvis's '68 Comeback Special, and a scary moment when an audience member nearly died mid-show.
12moments
- Louis CK wanted Tim to do a club set without a theme, just murder an hour like he's on the road.
- Tim styled the special after Elvis's 1968 Comeback Special, building a 10-by-10-foot stage with the audience surrounding him.
- The stage setup was almost in-the-round but more of a square, recreating that intimacy where people can see each other's faces.
- Tim hates having specials because you're doing it on cue, whereas live performance has genuine stakes.
- A woman in the audience passed out 20 minutes into the first show, stopping the performance and throwing Tim off.
- They didn't do this for ten thousand dollars at a club; they made something special and put it on Louis's website without asking a middleman.
- Tim shot in Denver at a big theater but doesn't want to do that again, thinking smaller next time might work better.
- Tim's done specials at the Village Underground and here; theater performances are different because he can't see people's faces and ends up doing more crowd work.
- Louie's independence means no network notes and the freedom to call the special whatever he wants—Tim pitched "Remember AIDS" as a title.
- Streaming services and networks are losing money and will eventually need to make profit-driven decisions, so the era of making garbage might be ending.
- Tim contrasts old publicity tours set up by publicists with shooting the shit with friends on a podcast at 11 PM, which is easier and reaches thousands.
- Tim jokes that he might have shit his pants during the conversation.
TampaLouis C.K.Mike CaltaVillage UndergroundCoastal creativesDenverRound RockElvis's 68 Comeback Special+1 more
- 4 min
Why Streaming Networks Won't Buy Podcasts
#Tim and Bobby discuss the creative freedom of self-releasing specials versus old media gatekeepers, speculating whether CBS or Netflix would ever buy up comedians' podcasts and control, and why streamers avoid the 'smoke.'
7moments
- Podcasters now control their own audiences instead of networks controlling them and the content.
- Tim estimates a major network would pay 20 million dollars to buy and own a successful podcast.
- Taking network money means answering to somebody, but Tim would do the show his way regardless.
- Streaming services like Netflix likely won't buy podcasts because they don't want the controversy.
- Podcasts can't be improved much by throwing money and resources at them the way other content can.
- Tim and his guest can roll into a studio, talk to thousands of people, and be gone in minutes with minimal technology.
- Podcasting will never replace traditional comedy movies like Step Brothers or Anchorman.
- 3 min
The Comedian Who Cracks the Movie Code Will Change Everything
#Tim argues that podcasting killed late-night TV but comedians still haven't figured out how to make a great outrageous R-rated comedy movie, and predicts whoever does will be a game-changer, name-checking Bill Burr.
8moments
- A comedian from the current scene who figures out how to fund and make a movie will be a game changer.
- Modern comedies aren't funny anymore; the next ones need to be genuinely funny and edgy, with nudity and explicit content.
- Breasts and trans nudity should make a comeback in comedy films, citing Porky's and Kentucky Fried Movie as reference points.
- The next impactful movies will be outrageous and politically incorrect, depicting real-life depravity.
- Comedians have essentially replaced late-night TV with podcasts; late night no longer matters.
- Movies require significant funding and involve complex logistics, which is where comedians have struggled.
- Someone building a film from the ground up and selling it independently will change the game.
- Tim says it won't be him who makes that breakthrough independent comedy film.
- 1 min
Bringing Back Tits and Trans Tits in Comedy Movies
#Riffing off the movie discussion, Tim jokes that raunchy comedies need nudity to return, including a pitch for trans nudity in a Porky's-style film, and references The Hangover 2's trans character.
4moments
- Tim owns a tiny house in New Hampshire stocked entirely with Helix mattresses they sent him.
- Every guest who sleeps in Tim's guest room demands to know what mattress it is, then accuses him of lying when he says Helix.
- Tim says Helix is one of the really great companies because people don't realize they don't need to spend thousands on mattresses.
- He donates Helix mattresses to unhoused people on the street, stacking them in a van to send out.
- 1 min
Tim reads a sponsor segment for Helix mattresses, praising their quiz-based matching system and joking about donating mattresses to homeless people in LA.
1moment
- Tim pitches Helix Mattress's sleep quiz to determine how customers like to sleep
- 1 min
Continuing the Helix ad, Tim riffs that a citywide homeless sleep quiz is the real bottleneck preventing LA from building affordable housing.
3moments
- Los Angeles homeless population needs Helix Sleep mattresses, but the real problem is getting all 40,000 of them to complete the sleep quiz before affordable housing can be built.
- Tim pitches Helix Sleep deal: $200 off mattress orders and two free pillows at helixsleep.com/TimD.
- Many of his friends are losing their hair with no solution, but you can save the hair already on your head.
- 2 min
Tim reads an ad for Keeps hair loss treatment, joking about a friend who got visibly bad hair transplant surgery and became a social outcast.
3moments
- Tim explains Keeps as a prescription hair loss medication delivered online with virtual doctor consultations.
- Treatments take four to six months to see results, so starting early when hair loss begins is key.
- Tim describes knowing someone who got hair surgery and now looks visibly wrong, making him a social outcast.
- 2 min
Pitching the 'Comedy Camp' Survival Show
#Tim pitches a new show idea to Bobby: taking five comedians (Bobby Kelly, Russell Peters, Bill Burr, Jim Norton) primitive camping in the wilderness for several days, modeled after the show Alone.
7moments
- Tim is filming Comedy Camp in the summer, a show where comedians go camping in the woods.
- The concept is based on the survival show Alone, but with five comedians dropped in the mountains for five days instead.
- Tim says the idea draws from his Bushcraft party with Ari Shaffir and Joe List in the waywards.
- Russell Peters can't film this in Long Island because there are no hills or mountains there.
- Cast includes Russell Peters, Bill Burr, Jim Norton, and hopefully Beth Stalling and Shaquille O'Neal.
- No cell phones, no internet, no managers allowed during the five-day camping trip.
- Tim warns that people are going to die on this show.
AloneComedy CampBill BurrJim NortonAri ShaffirBeth StallingJoe ListRussell Peters+1 more
- 7 min
Debating Whether Someone Will Die on Comedy Camp
#They hash out logistics of the camping show — supplies, primitive camping rules, bear bags, tasks, and whether comedians could survive without cell phones, food, or comforts — with Tim insisting someone might die.
9moments
- Tim insists people will die on Comedy Camp; his co-host argues supplies and setup make it survivable.
- Primitive camping in National Forest with a four-hour hike, tent setup, and solo nights alone in the woods.
- Tim defends the woods as beautiful and meditative, then his co-host counters that the woods are pagan and satanic.
- Discussion of what food participants can bring: baked beans are permitted for one night.
- Russell Peters owns 19 Bentleys but may be snaring food; his father hunted tigers in India as a boy.
- Taking Jim Norton from his penthouse lifestyle and dropping him in the woods for four to six days.
- Tim describes hiking into the woods at night with Ari and Joe, explaining how darkness changes everything.
- When the sun goes down in the woods with no city lights, you can see galaxies and hear actual sounds around you.
- In complete darkness with only a fire, surrounded by nothing but sounds you can't identify—something is out there.
Jim NortonRussell PetersAri ShaffirJoe Roganprimitive campingPaul Virzi
- 1 min
Why the Woods Make Comedians Truer Versions of Themselves
#Bobby argues that stripping comedians of their usual environment and putting them in total darkness in the woods forces them to become real, unlike their curated podcast personas.
4moments
- Tim notes that Rogan gets the woods because it's his whole world, unlike most other comedians.
- Bringing regular people on a hike is one thing, but when you take comics out there it gets hilarious.
- When something unexpected happens in the woods—a sound, a presence—the comedy stops and comedians become real.
- Out in the woods, stripped down and exposed, comics still use their defense mechanisms, but the armor becomes genuine.
- 4 min
Bear Encounters, Riptides, and Ocean vs. Woods Round Two
#Discussion of real bear sightings in New Hampshire, bear spray vs. human mace, dangers of riptides in the Hamptons, and reigniting the ocean-versus-woods debate.
8moments
- Tim gets funnier as the sun goes down in the woods, especially on a multi-day camping trip.
- What happens to people on the second or third day camping without restaurant food — they become themselves and appreciate things more.
- Going to Guatemala with a friend made Tim appreciate America and the ability to drink tap water when he got home.
- Tim rejects the idea of taking comics to the Bronx at night to shoot, calling it too dangerous.
- Middle-aged gay guys on the beach are more dangerous to many people than lions, and tigers are easier to deal with than Jewish people.
- The ocean is tough and powerful — Tim's been in riptides and almost died, though he didn't know to swim diagonal at the time.
- The ocean is more powerful than the woods, and Tim doesn't enjoy it the way he enjoys nature in general.
- Tim concedes the ocean is more powerful than the woods but insists the woods are better anyway.
- 8 min
Rattlesnakes, Coyote Packs, and Planning Trip Logistics
#Bobby recounts real dangers from a previous camping trip with Ari Shaffir and Joe List — timber rattlesnakes in the Catskills and a terrifying coyote pack at 1:30am — while planning the season and safety measures for Comedy Camp.
15moments
- Tim explains the spring timing for the woods trip, accounting for mud season, bug season, and black flies.
- Planning tasks for the competition, including the possibility of sucking someone off as an option.
- Tim is funding the entire trip and donating money to charity, with each participant choosing which charity receives their winnings.
- Jim Norton starting a fire is going to be hilarious because he won't be able to do it after learning how.
- When Tim went out with Ari Shaffir and Joe Rogan, they didn't know how to hang a bear bag properly.
- Camping protocol requires taking a shit 150 feet away from camp or water and digging a hole.
- Shitting outside in the woods is one of the greatest shits you'll ever take once you get over the fact that you're doing it.
- Bear bags are necessary to hang all food in trees to avoid attracting bears into camp.
- Bears look adorable and cute but they'll murder you if encountered in the woods.
- Tim will be the guide for the trip, which he acknowledges is a little scary and terrifying.
- Dangerous wildlife in the woods includes timber rattlesnakes, mountain lions, and fisher cats.
- Timber rattlesnakes in the Catskills number in the thousands, and the second person in a hiking line is often the one who gets bitten.
- A pack of coyotes came into camp at 1:30 in the morning and everyone just sat in their tents frightened.
- Joe Rogan's response when coyotes attacked was asking 'what do we do about that,' and Tim said 'I don't know.'
- Tim predicts someone will die on the trip but that's okay.
- 4 min
Picking Who Dies First and Tim's Beach Alternative Show
#They joke about which comedian would die first on the camping show, and Tim proposes an easier beach-based alternative version with bonfires, football, and Mister Softee instead of the woods.
8moments
- Tim argues the show needs someone to get sacrificed to make it work.
- It would be funnier if Tim himself died and someone took over the show.
- Tim pitches an alternative beach version instead of a woods show: five comedians, swimming with great whites, fish sandwiches, Carvel ice cream, bonfire, and night football.
- Guest admits he got jealous when Tim went hiking with Ari and Joe, wants to experience the outing.
- Tim plans an overnight hiking trip to the Mohawk Mountain House with the guest that summer.
- Tim offers his hammock for the guest to sleep in during their wilderness camping trip.
- Jumping in the lake at night is different, Tim notes, invoking Jeffrey Dahmer's observation about darkness.
- Tim says he doesn't know why comedians don't all buy each other's specials and commits to buying the guest's.
- 2 min
Tim and Bobby plug the Kill Box special again, reminisce about Bobby getting his start filling in on Opie and Anthony with face paint and offending Colin Hay, and close out the episode.
4moments
- Bobby Kelly's special is called Kill Box, available on LouisCK.net and KillBox.com
- Tim recalls Bobby being one of the first people to put him on a podcast
- They did a show together when Opie and Anthony took a day off—Tim painted Bobby's face like a clown while Tim looked like Charlie Casey
- Tim offended Colin Hay by making a joke about his dead friend during that same episode, then Hay had to play a song while pretending everything was fine
Bobby KellyDan SotoOpie and AnthonyColin HayLouis C.K.