Episode 137 · The GaS Digital / Ray Kump Era
Bert Kreischer
with Bert Kreischer
Mar 2, 2019 · 1:05:37 · 21 segments, 158 moments indexed
- 1 min
Show intro music and applause before conversation begins.
1moment
- 0:02Show intro: Tim Dillon Is Going To Hell
- 1 min
Bert Kreischer talks about the intensity of his current theater tour, going back into therapy, and friends like Sagar and Joey Diaz joking/betting about whether he'll die on the road.
2moments
- 1:07Bert calls the tour the best thing he's ever done in his life.
- 1:33Bert reveals Sagar told him he'd die on the road during the tour.
Joey DiazSagar
- 4 min
Bert discusses the gap between his shirtless stage persona and his actual healthier habits, compares himself to comics like Ralphie May whose tour bus lifestyle destroyed them, and describes reframing his mindset about back-to-back tour dates. He also introduces his tour crew, including his assistant Cobra.
9moments
- 1:55Tim explains the gap between his shirtless stage persona and who he actually is—someone who tries to eat healthy and doesn't drink every single night, though he does drink more than average.
- 2:35Parts of his personality don't fit into his branding; he worries fans assume he's like the hard-living comedians he admires—Kineson, Pryor, Hedberg, Ron White, Ralphie May.
- 3:03Ralphie May's biggest problem was the tour bus—he'd get on it, stop exercising, eat pills, smoke weed, and gain weight.
- 3:26Tim recognizes the same trigger on a tour bus: the constant invitation to drink, get high, stay up all night, order McDonald's—the traveling party mentality.
- 3:55The scheduling grind during multi-show runs tempts him; Thursday night leads to Friday's double-header, then a weekend of shows before Monday departure.
- 4:38Tim changed his perspective by reminding himself he'd worked his entire career to reach this—selling out theaters and doing two shows a night was once unimaginable.
- 5:15Now he focuses on the moment: he gets to work on his set twice each night, fix mistakes in the late show, and refine material on the bus.
- 5:36He's staying regimented on the road—limiting drinking and eating excess—and adding things he enjoys like treadmill walks or sauna sessions at YMCAs.
- 5:53His tour bus crew: Cobra (his assistant), Dean (bus driver), and Travis (second bus driver).
Ralphie MayMitch HedbergRichard PryorRon WhiteSam KinesonCobraDeanTravis
- 3 min
Riffing on giving people nicknames, listing the comics who've opened for him on various tour legs, and explaining why he turned down acting opportunities because sitting around on a film set waiting depresses him.
7moments
- 6:12Tim explains why nicknames make life more interesting, giving the example of Tony Hernandez meeting another Tony and refusing to call him by the same name.
- 6:45Tour lineup includes Jesus Trejo, Shane Torres, Dusty Slay, Dave Williamson, and Leanne across multiple runs of exclusively theater dates.
- 7:06Tim originally planned to tour and then take three months off, but decided to tour the entire fucking year instead.
- 7:30When asked about TV shows or movies, Tim says fuck it all—stand-up comedy is the only thing he actually likes.
- 7:43Sitting in a trailer on set triggers depression in Tim because he's not creating, writing, or in charge of the project.
- 8:04A PA told Tim they didn't need him yet, and he snapped at being spoken to that way on a previous acting gig.
- 8:18Production told Tim to stay in his trailer while he just wanted to watch and learn on set, which made him lose his mind.
Tony HernandezJax MediaDave WilliamsonDusty SlayJesus TrejoShane TorresTony Woods
- 2 min
Bert tells a story about getting a blowjob from a famous actress who broke off to ask about his production deal, using it to riff on how actors (unlike writer-producers like Amy Poehler or Tina Fey) are basically soulless vessels who just say other people's words, comparing pure actors to Jussie Smollett.
5moments
- 8:41Some people get into comedy just to be pampered in a trailer as the third lead on a sitcom.
- 9:02Tim got a blowjob from a TV actress at 27 and thought he'd achieved the dream until she stopped mid-act to ask about his production deals.
- 9:58Since that encounter, Tim concluded all actresses are broken — they're only interested in networking and information.
- 10:31Actors remain completely unaffected by criticism, which Tim describes as true sociopathy.
- 10:47Tim's definition of a "straight up actor": someone whose only dream is to say other people's words, like a person who traces instead of creating art.
- 4 min
Discussion of Instagram influencer culture, Bert's history vlogging and hosting on Travel Channel (Bert the Conqueror, Trip Flip), and how a new network president fired him, sending him into a depression that started his therapy journey.
7moments
- 12:27Tim got into vlogging three or four years ago and produced about 40 to 50 episodes, getting deeply involved in editing, music, and the creative process.
- 13:05Getting fired from Travel Channel happened after the vlogging experiment; a new president wanted her own people and drove the network into the ground.
- 13:26Tim started therapy after getting fired from Travel Channel—he says it was the lowest point of his life.
- 13:56Travel Channel gig came with major money—10 grand a week initially, then an overall deal for a quarter million dollars over two years, which fundamentally changed his financial situation.
- 14:20When he got the original Travel Channel deal, Tim lit a joint, opened champagne, and told his wife they didn't have to worry about money for two years.
- 14:40Tim kept renegotiating contracts with Travel Channel for more money, thinking that was going to be his career path until he got fired.
- 14:50He found out about the firing while taking a walk, trying to lose weight during a fat-shaming period with Tom.
- 4 min
Bert recounts the exact day he got the call firing him from Travel Channel while scheduled for a vasectomy, losing money on canceled Funny or Die tour dates, and hitting rock bottom before discovering vlogger Ben Brown's videos as inspiration.
10moments
- 15:02Tim was scheduled for a vasectomy on the same day his house was being demolished and he had a Funny or Die tour lined up.
- 15:23Travel Channel called to drop him, going a different direction without explanation.
- 15:46After calling his wife to cancel the vasectomy, he learned Funny or Die cancelled all his booked dates without refunding the travel costs he'd already paid.
- 16:06Tim cancelled his entire tour from August to December because he'd been counting on the Funny or Die dates instead.
- 16:20At his lowest point ever—Showtime special premiering in November to no audience, house being demolished, out thousands on cancelled travel—Tim started therapy.
- 16:39His only reprieve came when he discovered Ben Brown's vlog in Philadelphia and decided he wanted that kind of life.
- 17:13Joe Rogan's example: at the top of his game with Fear Factor and the Comedy Store, he called out Carlos Mencia and lost everything the next day.
- 17:38After being banned from the Comedy Store and dropped from Fear Factor, Rogan started the JRE podcast just to create something for himself.
- 18:12Bill Burr did three Comedy Central specials and asked Tim at the Improv whether that was it—just unwatched specials forever.
- 18:24Tim identifies hitting rock bottom as the moment comedians stop chasing the industry and start creating for themselves.
Travel ChannelJoe RoganFunny or DieNetflixBill BurrJoe Rogan ExperienceThe Comedy StoreShowtime+7 more
- 4 min
Bert and Tim discuss how career bottoms (Rogan getting banned from the Comedy Store after calling out Carlos Mencia, Bill Burr's unwatched Comedy Central specials) preceded major breakthroughs, and Bert explains how his own lowest point led him into vlogging and eventually Instagram Stories.
9moments
- 18:48Tim started in stand-up after the mortgage industry crashed and his house was being foreclosed.
- 19:16Starting a vlog excited him even though he was at the lowest point of his life.
- 19:38The vlog eventually cannibalizes his life—he was so focused on getting shots he didn't celebrate his own birthday.
- 19:56Casey Neistat told him Snapchat would replace vlogging, but Tim couldn't connect with it because everyone was fifteen.
- 20:29Instagram Stories came out and Tim immediately knew it was the platform for him.
- 20:47The swipe-up feature on Instagram let people go straight to buy tickets from tour mentions.
- 21:17Tim realized he loved making funny promo videos and setting up camera shots on Instagram.
- 21:48Dane Cook was severely depressed about his career, then booked a movie the next day and his mood flipped completely.
- 22:15Tim calls the unpredictability of comedy—the lottery-ticket nature of it—an unhealthy way to live.
- 2 min
A story about visiting a depressed Dane Cook who got a movie role overnight, used to illustrate how unstable and unhealthy the emotional highs and lows of the entertainment business are compared to a normal career like his grandfather's.
4moments
- 22:33Tim compares his grandfather's steady career as a general contractor to the lottery-ticket nature of entertainment, where you might book a movie overnight or lose everything on a whim.
- 23:01A commercial actor friend keeps getting close to major national campaigns but loses roles over arbitrary reasons — like the CEO's wife disliking his mustache.
- 23:25Tim argues the flip side: you get the opportunity to perfect a craft over years, then suddenly someone recognizes you're ready, like a contractor finally building in the right neighborhood.
- 23:51Tim spent seventeen years doing stand-up and claims he was probably funnier after all that work than he is today.
- 4 min
Bert details the unglamorous, low-ticket New Year's Eve show before the Machine story clip went viral on Facebook in December 2016, instantly transforming his ticket sales the following weekend in a blizzard in New Jersey and then Buffalo.
9moments
- 24:21Showtime Special comes out, no one sees it.
- 24:48Venue lost money on the weekend; Tim wanted to give them a refund out of guilt.
- 25:17Three years earlier, Tim's guarantees across the board were just 10 grand with $500 bonuses per show.
- 25:44The machine story goes viral and Tim sells out every single show at Stress Factory.
- 26:16Tim asks the crowd how many came from Joe Rogan's podcast, then realizes the rest came for the machine video.
- 26:40That viral machine video becomes a genuine game changer for his career.
- 26:56Vinnie gives Tim two grand extra, which leads him to start the weight staff raffle.
- 27:19Next weekend in Buffalo, same blizzards, same sellouts—17 years in, suddenly an overnight sensation.
- 27:37Machine story had been in his special before Facebook allowed it to go viral.
the machine storyVinnie BrandStress FactoryLebedy LiveShowtimeJoe Rogan's podcastFlorentine
- 2 min
Bert describes the aftermath of the viral Machine story — fans discovering he had a deep well of other stories and jokes, comparing his sudden visibility to Cardi B, and imagining the alternate timeline where the video never went viral.
5moments
- 27:50Tim explains how a viral Facebook moment from a special changed everything for Bert's visibility and booking power.
- 28:05People started coming to shows realizing Bert could actually do stand-up comedy, not just tell one viral story.
- 28:18Bert had twenty stories as good as the bear fight because he was a trained comic who could work a room and handle hecklers.
- 28:35His connections to Joe Rogan and Tom Segura added credibility once people knew his name.
- 28:51Tim compares Bert's sudden fame to Cardi B—someone nobody heard of until one viral moment made her unavoidable.
- 5 min
Bert tells the full story of the infamous live podcast meltdown with Doug Benson in St. Louis, where he brought 200 Burger King cheeseburgers on stage against Doug's wishes, escalating into a real on-stage fight and fallout with another comic friend.
10moments
- 29:41Tim introduces the concept of "survivors remorse" from his lowest point in 2016.
- 30:13He flew to St. Louis early to do a podcast with Doug Benson on a Wednesday night.
- 30:29Tim decided to buy 200 cheeseburgers to give to the fans at the show.
- 30:49He called Burger King from the airport tarmac with the idea, demanding they be ready in 30 minutes.
- 31:21Doug explicitly asked Tim not to bring the cheeseburgers on stage before the show started.
- 31:56Tim ignored Doug's request and brought the cheeseburgers out anyway, telling Doug he thought he was joking.
- 32:32After Doug hid the burgers and staff kept retrieving them, the situation escalated into a legitimate meltdown.
- 33:13Tim left the stage screaming with Doug, then decided to take his shirt off and walk through the audience with the burgers.
- 33:43He kept getting laughs and didn't realize he was doing everything Doug explicitly asked him not to do on his show.
- 34:09Doug came to Tim's hotel room the next day, and they did a podcast to talk it out and patch things up.
Doug BensonHelium St. Louis
- 2 min
After the Doug Benson fallout, Bert recalls a depressing weekend in St. Louis with poor ticket sales, seeing a down-and-out man outside a convenience store, and a club manager condescendingly asking if he was just going to be a road comic forever.
6moments
- 34:29Tim's friendship with another comic fell apart after they attacked him, and he felt deeply betrayed.
- 35:12He sold 400 tickets across the St. Louis weekend while depressed about the fallout with Doug.
- 35:27Driving to Friday press, the club manager asked condescendingly if Tim was just going to be a road comic forever.
- 36:11Tim had always viewed being a road comic as a privilege, something only a small group of talented people get to do.
- 36:28The manager's tone made Tim realize he was being looked at like a loser, the same way he'd just been looking at a struggling man outside a St. Louis convenience store.
- 36:38The irony: the person judging Tim was just a manager at a comedy club in St. Louis.
DougSt Louis
- 4 min
Bert explains how the fat-shaming bet with Tom Segura (started by Ari Shaffir) caught fire online, how he leveraged his video editing skills to escalate it with weigh-ins on Instagram, and how it coincided with his career finally taking off, tying back into his 'survivor's remorse.'
11moments
- 36:54Tim got into a CBS development deal but had been in about 12 deals total that went nowhere.
- 37:17He felt out of control of his career until he started a vlog, which marked his turning point.
- 37:48Tom Segura started fat-shaming him as a joke, initially without Tim realizing it was happening.
- 38:19Ari Shaffir kicked off a weight-loss bet between Tim and Tom that caught fire with fans.
- 38:36Tim realized he had an advantage over Tom because he could edit and post videos himself quickly.
- 39:04Weigh-in posts on Instagram, especially a beardless photo, went viral and changed everything overnight.
- 39:15The viral moment led to ticket sales and made Tim confront survivor's remorse about his sudden success.
- 39:43He had been on Travel Channel, which nobody cared about, before Burr and Rogan told him to focus on stand-up and podcasting.
- 40:02Bobby Kelly reminded him on a cruise that other comedians are still grinding on the road.
- 40:20Talented comedians who don't connect with audiences often ignore advice, which Tim describes as the only advice he's actually taken.
- 41:02Tim says the only advice he hasn't ignored is the guidance that shaped his career decisions.
Bill BurrJoe RoganTomTravel ChannelBobby KellyCBSAri ShaffirDavid J. Nash+1 more
- 3 min
Bert explains his philosophy of ignoring advice from peers who told him to retire the Machine story, and contrasts comics who perform for themselves and their fans versus those who chase approval from other comics.
9moments
- 41:11Tim has ignored all advice to stop doing things his way.
- 41:21Everyone in comedy tells him to retire the machine story, but he keeps telling it at the end of his sets.
- 41:49The forklift operator or dialysis patient who gets one night out wants to see the story that made them come, not just new material.
- 42:18Dave Stroup once asked Tim not to tell the machine story because angry customers were waiting at the bar afterward.
- 42:42Some comedians perform for other comics' approval rather than for the working people in the audience.
- 43:06Comics copy each other's moves—new hours, podcasts, jujitsu—instead of being authentic to what they actually want.
- 43:39Bill Burr and Ari Shaffir moved to New York for their own reasons, not because Joe told them to.
- 44:03Tim believes you have to respect people but ultimately ignore their advice and follow your own direction.
- 44:27Too many comedians are concerned with what others think instead of being themselves, which actually limits their talent.
Joe RoganAri ShaffirBrendan SchaubBill BurrDave StroupTony Delia
- 4 min
Riff on comics who copy others' styles (buying certain shoes, doing jujitsu, doing act-outs) rather than being authentic, including Bert's admission his early act ripped off David Tell and Dane Cook.
10moments
- 44:41Tim admits his early special was a David Tell Dane Cook ripoff, imitating the fun party frat guy persona.
- 45:04Comics copy successful acts like Sebastian's act outs without understanding why those acts originally worked.
- 45:51Tim describes watching comedians repeat identical jokes across multiple specials instead of challenging themselves.
- 46:08Bill Burr as the counterexample—switching up his approach with act outs and different material each special.
- 46:26Stan Hope told Tim he'd exhausted his great jokes, then called him one day getting grapefruit and vodka, trying to write knock knock jokes.
- 47:00Tim spent a week convinced he could write great knock knock jokes because those writers weren't funnier than him.
- 47:23What if a comedian ended a special on three original knock knock jokes instead of crowd work?
- 47:46Tim became obsessed with Norm McDonald and decided he needed to write a guy walks into a bar joke.
- 48:03Found his guy walks into a bar joke in a Starbucks on April 13th—the most fun he'd had in comedy.
- 48:19Tim's challenge: keep his strengths in storytelling while disciplining himself in classic comedy forms like knock knock and bar jokes.
- 5 min
Bert discusses pushing himself creatively — Stanhope's obsession with writing original knock-knock jokes, his own quest to write a great 'guy walks into a bar' joke inspired by Norm Macdonald, physical comedy inspired by Seinfeld, and his new cooking show Something's Burning.
12moments
- 48:44Tim recalls Jerry Seinfeld saying if you can jump to get a bigger laugh, why not jump.
- 49:07In therapy yesterday, realized he hasn't done anything outside stand-up that truly inspired him creatively.
- 49:22Ready to work on his set, put it on ice for a month, then shoot something different that he's writing and in control of.
- 49:46With podcasting, he gets excited about gadgets and finding ways to get different angles and make it better.
- 50:17Can't keep finding the bottom like a drug addict—need to find a bottom only if you're on the wrong path.
- 50:43Tim isn't selling the tickets he'd want; certain markets are better than others, it's all slow-building.
- 51:09Stanhope's strength is being authentically himself across the board, which is where his success is popping.
- 51:27New York comics have been building podcasts that aren't top of the charts, learning to do podcasts and stand-up simultaneously.
- 51:56When Stanhope appeared on Rogan, he was phenomenal because he's been doing podcasts for nine years, going toe to toe with other comedians.
- 52:36Bobby Kelly's podcast is one of the best and ground zero for New York podcasting—spawned everything from it.
- 53:09Joe Rogan isn't an LA comic; he's a Boston comic with all his roots in the East Coast.
- 53:27Stanhope had done all those different podcasts and had all those experiences so he could be funny on this platform.
Something's BurningBobby KellyJerry SeinfeldLegion of SkanksJoe RoganLisa Traeger
- 3 min
Bert describes feeling overprepared and calm backstage at an industry showcase full of nervous younger comics next to Tom Segura and Jimmy Carr, crediting his years of experience for the ease of the moment.
8moments
- 53:56Tim describes being backstage at a young comics showcase with Tom and Jimmy Carr, surrounded by comics who were four to ten years into their careers.
- 54:16Having fifteen to sixteen years of experience, Tim planned to cruise through his ten-minute set, confident he already knew his material.
- 54:28Tom explains the difference: the young comics aren't prepared for the moment, while Tim is prepared—they're still questioning whether their jokes land, but he knows what he's going to say.
- 54:52Tim destroyed on stage and realized afterward he was ready for the opportunity in a way the younger comics weren't.
- 55:09Thirteen or fourteen years prior, Tim appeared on Last Comic Standing 2, which broke his heart when he didn't make it to the house while everyone else did.
- 55:25The Last Comic Standing appearance was in 2004, when the show had 13 to 20 million viewers—comparable to Joe Rogan's current audience size.
- 55:57Tim compares Rogan's 13 million to the broadcast numbers, noting Rogan's audience is highly engaged and shares the content, making it more intensive.
- 56:11Tim mentions getting a duck from Georgia after the Last Comic Standing rejection, trailing off into another memory.
- 3 min
Bert recounts the devastation of losing on Last Comic Standing 2 in 2004, not making the finalist house, and being excluded from a celebratory lunch by friends, plus reflecting on how winning too early would have ruined him.
8moments
- 56:16Tim was kicked off Last Comic Standing while pregnant and asked Bonnie McFarland, Gary Goldman, and Todd Glass to join them for lunch, but they declined because they didn't want to celebrate victories in front of a loser.
- 56:55The comedians told Tim they wanted to talk about good things going on but couldn't do it in front of him.
- 57:12Barry Katz was in the hotel gift shop with contracts for Tim to sign for a Shorties appearance, which Katz called a nice consolation prize.
- 57:27When Tim felt down, Barry Katz tried to cheer him up by saying he was having a kid, which Tim felt didn't help because he considered himself a loser.
- 57:46Tim claims he wouldn't have had the material to back up a Last Comic Standing win anyway, with only twenty minutes of comedy.
- 57:57Had Tim won, he would have become another forgotten winner people can't remember, unlike Gary Goldman, John Efron, Josh Blue, Amy Schumer, and Doug Benson.
- 58:16One obscure Last Comic Standing winner now works at SeaWorld and teaches comedy, which Tim finds hilarious even if unintentionally.
- 58:40Another past winner had cancer and Tim thought he'd wish he had that guy's career instead.
- 5 min
Bert compares himself to a shark-like top NYC realtor who can never turn off work mode, describing how he's constantly mining daily family life (his daughter's boner question, translating comic names to Leanne) for material, and admits he's only 'off' about 2% of the time.
12moments
- 58:53Tim notes that many comedians on the road don't have wives or kids, which he sees as essential to having a life beyond comedy.
- 59:10Story about realtor Dolly Lenz, who sold $9 billion in real estate over 20 years and can never turn off her competitive drive, even at dinner with her family.
- 59:47Tim identifies with that mentality, pulling out his phone during lunch to write jokes while his wife and cousins are talking.
- 1:00:08His daughter Isla asked him what a boner was during a conversation about body insecurities, right after he was workshopping a joke about his own anatomy.
- 1:00:40Tim describes his joke material: his pubis looks like a single shooter on a grassy knoll.
- 1:00:51Leanne doesn't remember names of people Tim mentions, so he has to describe them as characters—like 'gay guy doesn't look gay' or 'angry cop redhead.'
- 1:01:19Story about his buddy Pete, who bought their car, painted it white, and sold it through his dealership.
- 1:01:46Tim says Joe Rogan definitely knew he was gay but genuinely doesn't care about anything outside of aliens and topics beyond that.
- 1:02:33Leanne estimates Tim turns off the comedy brain 2% of the time, though she admits that's an exaggeration for humor.
- 1:03:05When the kids get home Tim can turn it off somewhat, but he struggles to put his phone down; once he does, he stays present.
- 1:03:21During Sober October, Tim is completely checked out mentally, focused on the competition and texting with the other guys rather than being present with his family.
- 1:03:40Christina asked to podcast with Tim weekly during Sober October because it's apparently not fun for the partners—Joe's wife, Ari's girlfriend all hate it.
- 2 min
Closing riff about the group's annual Sober October challenge (heart rate monitor competitions, past hot yoga year) and Bert's closing thanks, invitation to have Tim on his podcast, and goodbye to Leanne.
4moments
- 1:04:03Hot yoga was the challenge one year, and Tim found it genuinely fun.
- 1:04:35Tim has been sober seven years but might reverse it in October—a month of getting fucked up every day instead.
- 1:04:46Tim tells his guest he genuinely appreciates them and offers to fly them out anytime they feel stagnant.
- 1:05:09Tim and his friend have spent years talking exclusively about what their lives would be like if they were gay.