Episode 253 · The Ben Avery Era
#253 - Jenner's Joyride | The Tim Dillon Show
May 23, 2021 · 1:08:49 · 387,000 views · 21 segments, 130 moments indexed
In another family friendly classic, Tim discusses Caitlyn Jenner's run for Governor of California, Bitcoin's big tumble, The Menace Lori Lightfoot's ongoing Chicago shenanigans, and why you can't buy true friendship.
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- 1 min
Cold Open: Studio Move to Austin
#Tim opens the show apologizing for the audio-only episode, explaining the studio is moving to a new space in Austin but will look the same.
2moments
- Tim opens with contempt for fans, noting how disrespectful it is to do audio-only episodes.
- The show is moving to a new studio space in Austin next week with upgrades coming.
- 5 min
Defending Blown-Off LA Comedy Spots
#Tim explains why he skips or leaves comedy club spots in LA, distinguishing between his own headlining shows and quick 10-minute guest sets, using the "Haha Comedy" parking lot gig as an example, and telling fans to support comedy generally, not just him.
10moments
- Tim apologizes for canceling LA comedy spots because he's no longer in the city; the Instagram beach and sushi photos are from years ago.
- When doing a spot on someone else's show, Tim performs 10-15 minutes without control over timing or the overall event; LA traffic and other obstacles sometimes make it impossible to reach multiple bookings.
- Tim walked into the HaHa Comedy Club—an outdoor alley venue with about ten people—and walked back out because he didn't want to be there.
- At the HaHa, a white girl in a Bob Marley hat was on stage talking about aliens landing and going on Rogan to do DMT; Tim had no involvement in booking her.
- Tim usually headlines his own road shows, which he attends and performs well at; he tries to do spots at other venues but faces obstacles.
- Tim was on the way to a spot, fell into a sushi restaurant for three hours after avoiding a gang of Palestinians, and couldn't make it to the gig.
- The distinction matters: a headlining show is different from a spot where he's doing ten minutes on someone else's lineup without knowing what's happening.
- Tim recommends watching Barbie Starlet instead of attending his spots; the movie has no plot or jokes but is brightly colored and serene with SNL alumni.
- If people bought lots of tickets to the HaHa parking lot expecting to see Tim's full set, he apologizes and offers to get them into headlining shows instead.
- Doing spots is something Tim's done for twelve years, but it's not as fun anymore.
Barb and Star
- 1 min
Anthony Jeselnik's Alt-Right Comedy Article
#Tim complains about having to be cordial backstage with Anthony Jeselnik, who shared a New Republic article accusing comedy of having an alt-right problem, despite Jeselnik's own history of dark jokes.
3moments
- Anthony Jeselnik made his bones doing Boston Marathon bombing jokes, then decided he's the arbiter of what's appropriate to say on stage.
- Tim admits Jeselnik's comedy isn't for him; he's more interested in human beings and carbon-based life forms.
- Jeselnik shared an article seeking to take away the careers of people Tim knows, yet Tim still has to sit with him in green rooms and make small talk.
Anthony JeselnikThe New Republic
- 3 min
Lori Lightfoot, Batman Villain Mayor
#Tim riffs on Chicago mayor Lori Lightfoot's fashion, her refusal to talk to white reporters, and jokingly proposes reporters do blackface to interview her, fantasizing about a Caitlyn Jenner/Lightfoot presidential ticket.
7moments
- Tim criticizes LA comedians for thinking they can do open mics forever without affording the high cost of living.
- He describes his own housing situation and plans to make content and do shows on the road instead of chasing LA spots.
- Tim lists all the obstacles to getting to comedy spots: violence, homelessness, and simply finding hotel valets more interesting.
- Lori Lightfoot, the mayor of Chicago, is someone Tim is obsessed with and describes as a menace destroying a great American city.
- Lightfoot looks like a Batman villain, wears ill-fitting clothes, balloon pants, fedoras, and walks around like she stepped out of a comic book.
- She now refuses to speak to white reporters and will only do interviews if journalists appear in blackface.
- Tim imagines Lightfoot walking down the street in a zoot suit with a fedora and cane, hitting homeless people as a true villain.
- 8 min
Caitlyn Jenner: True Diversity and the Fatal Car Crash
#A long riff praising Caitlyn Jenner as an example of "real" diversity versus mediocre diversity, retelling her Kardashian household dynamics, and joking that she doesn't dwell on the fatal 2015 car crash the way normal people would.
10moments
- Tim on the blackface absurdity of trying to interview Lori Lightfoot, who he calls a goon and offers to hire a Black translator for instead.
- Tim's dream presidential ticket: Caitlyn Jenner for president, Lori Lightfoot as VP playing the Dick Cheney power player behind the scenes.
- Tim argues Caitlyn Jenner represents true diversity—actual greatness—unlike the country's preference for mediocre, ethnically ambiguous people with identical worldviews.
- Caitlyn's credentials: Olympic decathlete with a gold medal, someone who has truly lived many lives and what California needs.
- Tim notes Caitlyn is a country club trans person who murdered two people in a car and acts like it never happened, just remembering gold medals and better times.
- During the Kardashian years, Caitlyn was cooking up a comeback while playing it close to the vest and golfing quietly, an afterthought in that Armenian Calabasas household.
- Caitlyn likes people who do things well—law and order, money, country clubs—and the only Mexicans she's spoken to gave her guacamole.
- Tim argues America needs more trans people from Caitlyn's background, not trans nerds or Tumblr trans people, the way it needs gays who look like dock workers or crooked cops.
- White women keep fashionable gays in their purse to interpret while drunk in Orange County; gays as flight attendants can do drugs and have casual sex across the country.
- What the country actually needs: a country club trans person pulling up in a Bentley, stepping out in Christian Louboutins, sitting in a restaurant and being unhappy about the tent on the way in.
Caitlyn JennerLori LightfootLouis C.K.Yes or yes
- 5 min
The Ideal Trans Person: Country Club, Not Tumblr
#Tim argues society needs wealthy, unapologetic trans and gay figures like Jenner rather than "tumblr" or "anime" types, praising her toughness and Sean Hannity interview style, then gets interrupted by a call about a cabana.
8moments
- Trans people should include a wealthy, out-of-touch trans Olympian with money and no guilt—the ideal representation.
- Tim defends Caitlyn Jenner as tough and unsentimental, unwilling to tolerate whimpering about hardship.
- His old joke: we need violent gay people and insensitive trans people with money who aren't ashamed of success.
- Caitlyn interviewed Sean Hannity in her airplane hangar—a spectacle of political theater, not primarily about her transition.
- Caitlyn speaks like Trump, off-the-cuff, calling herself a disrupter who will shake up California.
- California should have Caitlyn Jenner as governor, balancing her trans identity against her millionaire conservatism.
- A chief executive needs not to dwell on past actions—Caitlyn doesn't spend a minute thinking about the people she killed in the car accident.
- Tim compares Caitlyn's ability to move on to George H.W. Bush, who didn't think much about his partner's death in a plane crash.
Caitlyn JennerSean HannityArnold SchwarzeneggerLori LightfootGavin NewsomGeorge H. W. Bush
- 1 min
Cabana Wait List Interruption
#A brief real-time phone interruption about a hotel cabana becoming available while they're mid-show, and Tim can't leave to take it.
2moments
- Tim notes they're on a wait list for a cabana but can't leave the show to use it.
- Caitlyn Jenner prioritizes pool access over thinking about the two people she killed in a car accident.
- 2 min
Tim reads an ad for Acre Gold, a subscription service that lets you buy physical gold bars monthly and ships them to your home.
3moments
- Acre Gold subscription lets you buy gold bars starting at $30 a month, with a new $100 monthly option for a 5-gram bar.
- Tim explains the appeal: you invest in physical gold without paying the full price upfront, and it ships discreetly once you reach the threshold.
- Acre Gold is one of the few affordable tangible things you can buy that will actually be worth something in five years.
- 1 min
A string of sponsor reads covering ShipStation shipping software, BetterHelp therapy, Keeps hair loss treatment, and Gabi insurance comparison.
1moment
- Tim abruptly pivots to a joke about who someone killed as the ad read ends.
- 3 min
Details of the Caitlyn Jenner Car Crash Victims
#Ben reads details of who Jenner actually killed and injured in the crash (Kim Howe and the injured Wolf/Maurer family), and Tim jokes about the settlement and dismisses the severity, tying it back to "cancel culture."
8moments
- Sheriff determined Caitlyn Jenner was driving her Escalade at unsafe speed when she rear-ended a 69-year-old widow, pushing her into oncoming traffic.
- Tim clarifies that only one person died in the crash, though the family that was hit sued over extensive injuries including to a one-month-old.
- Tim suggests the family suing Jenner over the crash sounds like they're committing fraud.
- Jenner agreed to pay out $800,000 to the family.
- The one-month-old infant was injured but turned out to be totally fine after hospitalization.
- Tim questions what accomplishments a 69-year-old widow could have had, implying her loss is less significant.
- Tim expresses relief that the baby survived, then suggests the baby's death would have strengthened his argument.
- Tim claims Caitlyn Jenner wouldn't let even killing a one-month-old baby distract her from what she knows matters.
- 9 min
Playing Jenner's Homeless and Police Clips
#Tim plays and reacts to clips of Caitlyn Jenner's Fox News interview about homelessness and police, riffing on her fictional "fight the homeless" stance and inventing an absurd escalating bit about her using military-grade weapons against protesters.
12moments
- Caitlyn Jenner as California's next governor, planning to fight the homeless problem.
- Tim jokes about Jenner going on midnight raids in an Escalade, mowing over tent cities for the betterment of California.
- Jenner has committed to staying in the state and fighting the homeless instead of leaving.
- Tim's wife gives him weekly birthday presents leading up to June 25th, like Hanukkah.
- Jenner claims she pulls next to cops and thanks them for their service—Tim identifies this as a lie.
- Caitlyn speaks to very few people, mostly barks at her employees instead of interacting with police.
- Jenner says she'll use every force at her disposal to stop riots, including the National Guard and whatever else.
- Tim riffs on Jenner potentially endorsing direct energy weapons, radiation, cluster bombs, and magnets against rioters.
- Tim claims his dinner friends have weapons Sean Hannity has never heard of and describes what magnets can do to people.
- Sound weapons that pulsate energy waves through the air and knock people down are part of Tim's arsenal against riots.
- Tim signs off by saying they're supporting Caitlyn Jenner and moving on from the discussion.
- Transition to next topic.
- 4 min
Jimmy Kimmel's Bad Jenner Joke
#Tim dissects a clunky Jimmy Kimmel joke mocking Jenner's homelessness comments, arguing Kimmel is a hypocrite living in a wealthy area with his own homeless neighbors.
8moments
- Tim argues Jimmy Kimmel should stop complaining about his joke bombing and accept that Caitlyn Jenner is funnier.
- Kimmel's credibility problem: he hosted The Man Show about beer and breasts, now poses as a statesman.
- Tim mocks the Chelsea Handler tangent—she lost hearing in one ear after a vaccine, but he'd rather she recovered so he could tell her off.
- The actual joke Kimmel tried: whether calling a trans person an ignorant asshole counts as discrimination, since we don't discriminate against asshole-behavior itself.
- Caitlyn's complaint was that wealthy friends are leaving California because of homelessness—Kimmel's rebuttal that homeless people can't be flown over lands as wordy and bad.
- Tim notes how the late-night show cuts away right before the audience doesn't laugh, a standard edit to hide bombing.
- Hypocrisy check: Kimmel himself lives in the Hollywood Hills with plenty of homeless people nearby—same neighborhood as Matt Damon and other wealthy celebrities.
- Tim's takeaway: Caitlyn doesn't understand everyday Californians' needs, but neither does Jimmy Kimmel, who profits from his wealth while lecturing about homelessness.
- 4 min
A second round of sponsor reads for BetterHelp therapy, Keeps hair loss, and Gabi insurance comparisons.
4moments
- Tim pitches Keeps hair loss treatment, warning that two out of three men experience hair loss by age 35.
- He tells listeners to look in the mirror, acknowledge hair loss, and stop it by using Keeps before it's too late.
- Gabi insurance comparison platform lets you check quotes against 40 top providers in one place without ballpark guesses.
- Tim reports Gabi customers save $961 per year on average while protecting their information from spam and robocalls.
- 6 min
Bitcoin Crash Ahead of the Miami Crypto Conference
#Tim discusses the recent crypto market crash and worries about the upcoming Bitcoin conference in Miami, recalls dinner with the Winklevoss twins, and goes down a tangent about possibly having Asperger's.
10moments
- Bitcoin nosedived just before the Miami Crypto Conference scheduled for early June.
- Crypto market has lost roughly $1 trillion after Bitcoin dropped from $44,000 to $32,000 in five days.
- Tim worries the Miami conference won't be fun anymore given the crash—it was supposed to be a celebration of cryptocurrency, narcissism, and financial libertarians.
- Tim had dinner with the Winklevoss twins, who are true believers that crypto replaces gold as a reserve currency.
- Tim tweeted that governments aren't using Bitcoin to finance wars and bailouts, sparking backlash.
- Tim claims his lack of autism is a real problem—autistic people have laser focus that helps them master blockchain, while he lacks that hyperfocus.
- Someone once told Tim he has Asperger's, but he disputes it after checking the symptoms against himself.
- Tim insists he has great social skills but simply hates everyone.
- High integrity and mastery of routine are listed as Asperger's traits, but Tim says he's addicted to neither and doesn't think he has the condition.
- Tim texted the Winklevoss twins asking them to appear on the podcast to discuss the volatile week, but they haven't responded.
- 2 min
Cathy Wood and ARK Invest Crush
#A riff about Cathy (Cathie) Wood of ARK Invest, her stock price targets, and Ben's crush on her.
5moments
- Bitcoin conference in Miami is definitely happening, and people are saying bitcoin has hit bottom and will climb back up.
- Cathy Wood sets price targets that people think are crazy, but she's turned out to be right about Tesla.
- Guest was in ARKG and ARKK funds for a while and liked them.
- Discussion of whether Cathy Wood is the actual CEO of ARK or if there's a man making all the decisions behind her.
- Tim says he's getting nervous.
Kathy WoodTeslaARK (Ark Investment Management)
- 3 min
Fake Business Merch Hoodies
#Tim shows off new "Fake Business" branded merch hoodies and jackets, discussing fabric quality (cotton/polyester blend) and joking about the merch industry's staff.
6moments
- Tim announces the Fake Business hoodies are out, notes they didn't send his correct size.
- Merch people involved in the business are a little brain dead, not bad but not bright.
- Ben and Tim both did significant work on the Fake Business merch, and people dig the bit.
- Tim doesn't know what the fabric is but it's soft and hasn't given him a rash despite sensitive skin.
- The vest is 100 percent polyester, which Tim admits is not ideal.
- The hoodie is 80 cotton and 20 polyester—nothing wrong with that ratio.
- 1 min
Tim describes an upcoming book project mocking his parents' generation's parenting failures and occasional successes.
2moments
- Tim is working on a book called 'The Boomer Guide to Parenting' about the parenting strategies his parents employed on him.
- The book examines the childhood tactics and strategies—or lack thereof—that boomer parents used on people now in their mid-30s.
boomer parenting
- 1 min
Boomer Parenting Anecdotes
#Continuing the book topic, Tim shares specific memories like his father's advice not to overestimate your value, and dark jokes about boomer parents ignoring abuse.
4moments
- Boomers weren't helicopter parents—they dropped kids off everywhere and left them unsupervised.
- Tim's father told him 'never overestimate your value,' advice you couldn't give a kid today without it being called abuse.
- The book includes a chapter on things boomers got right when raising their kids, balanced against most of it being what they got wrong.
- Example of boomer negligence: a kid telling parents 'my teacher's molesting me' and them responding 'will you shut up.'
- 3 min
Crypto Exit Scams and Ben's Ethereum Payment Scheme
#Tim discusses crypto exit scams like DeFi100 and Ethereum overtaking Bitcoin speculation, then jokes about Ben and his wife scheming to fake blindness to extract money from him.
9moments
- Crypto coins like DeFi 100 are running exit scams with websites explicitly telling investors they've been scammed.
- DeFi 100 developers walked away with $32 million in investor funds.
- Tim argues crypto is clearly an asset bubble, but altcoins get people interested in the space, which the Winklevosses see as long-term positive despite the clownish element.
- Ethereum could overtake Bitcoin according to recent articles and analysts.
- Tim owns three Ethereum he received for an NFT that didn't sell for what he expected.
- Ben actually has five Ethereum, not three.
- Tim suspects Ben and his wife are constantly scheming to extract more money from him.
- Tim imagines Ben's wife coaching him to fake blindness with thick glasses to manipulate Tim into paying for a fake eye operation.
- Tim claims he caught the scam immediately when Ben visited the eye doctor.
- 2 min
You Can't Buy Friends (But You Can Buy the Governorship)
#Tim pays Ben in Ethereum and riffs on how money can't buy real friendship but can buy political office, referencing Jenner's campaign again.
6moments
- Tim compares himself to Caitlyn Jenner in understanding how parasites and scavengers target him.
- He describes people circling him like vultures landing on a longhorn, trying to rip flesh from his decaying body.
- Tim insists you cannot buy friendship in the world, despite theoretically thinking you should be able to.
- What you can buy, however, is the governorship of California—and it's been proven.
- Money works really well for buying power, which raises the question of why it fails for friendship.
- Tim corrects him: if love were bought, it would be conditional, not unconditional.
Caitlyn JennerEthereumCalifornia governorship
- 6 min
Closing Riff: Sobriety and Caitlyn Jenner's Unbothered Happiness
#Tim closes describing staring at an untouched bottle of gin as a sober alcoholic, reflecting on recovery, then returns to Caitlyn Jenner as the model of a person who truly knows who she is, ending with a mock prophecy of her presidency.
10moments
- Tim stares at a half bottle of Beefeater gin his friends left after their anniversary dinner, untouched.
- After 11 years sober, Tim describes having zero urge to drink the gin sitting in his hotel room overnight.
- Tim tells struggling listeners that realizing how much you can accomplish sober eventually removes drinking from your life entirely.
- Ben jokes that the bottle is just water, reminiscing about stealing their grandmother's booze and replacing it the same way.
- Comparing sobriety to Caitlyn Jenner's willingness to fight the homeless using direct energy weapons.
- The truly happy people aren't the overtly happy ones—they're annoying and on a drug that is themselves.
- Caitlyn Jenner is the happiest person in the world because she knows exactly who she is and transcends gender and class.
- Tim describes Caitlyn's perfect life: eating Mexican food served by white people at country clubs, thinking about her accomplishments.
- Caitlyn doesn't lose sleep—she uses any force at her disposal, with Raytheon and other defense contractors providing amazing weapons.
- Tim praises direct energy weapons over traditional guns, noting they terrify people and cause seizures but maintain law and order without killing.
Caitlyn Jennerrecovery from addictionRaytheon