PODCAST · comedy
Pessimistic at Best
by Sam Georgson
Welcome to Pessimistic at Best, a podcast for those with a penchant for frequent frustrations, personal gripes, unpopular opinions, honest observations, and the like. Hosted by Sam, your resident Pessimistic Patty, this weekly show operates on the belief that no complaint is too small. Each week, Sam sits down with a guest to explore the good, the bad, and the ugly. A surprisingly good country album by your favorite pop artist, a bad bang trim you gave yourself during a manic episode, a military homecoming video on the internet that made you ugly cry. The list is endless, and therein lies the beauty. Come on in, we saved you a seat!
Episodes
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Marine Mammal TikTok
Are you on marine mammal TikTok? If you haven't already been putting in your hours, I really can't recommend it enough! My feed has been completely consumed by seals, sea lions, and walruses alike, and I still can't get enough! James and I take to the podcast to expound on our special interest in...
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The Art of Escaping the Charity Solicitor
A woman in a vest clutching a clipboard just caught your eye from across the street and it's too late to turn around, wyd? Sarah and I take to the podcast to discuss getaway strategies for escaping the ever-annoying fundraising canvassers (no offense! we support the cause, we're just on our way…
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Accidentally Sending a Risky Text to Your Boss
Have you ever fired off a text to the wrong person? Was it an (accidentally) explicit text that you sent straight to your boss? Were you surprised to be offered a promotion afterwards? We might not all be this lucky, but Kate sure was — we have a good laugh about this one! Then we get into the...
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Making Out at the Party
What's your stance on public displays of affection? Are you open to a steamy hookup at the bar? As someone with a long-term partner, I'm typically abstaining from engaging in PDA myself (sorry, we can do that at home!), but Evan and I agree that catching a pair of strangers locking lips is the…
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Using Your Calculator to Determine the Tip
If you're good at math, you probably have no original opinions. Anyone can solve a problem that someone else solved first, but not everyone can develop a totally and completely unique point of view. Some of us were actually born interesting! Adam and I agree that it's actually perfectly fine and...
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Peak Luxury is Going Out for Breakfast
Name something more luxurious than dining out for breakfast, we’ll wait! A dinner reservation is (of course) classic but ultimately unoriginal, lunch is mostly giving fast-casual corporate escape—but breakfast? Aris and I wholeheartedly agree that breakfast is where it’s at. Then it’s time for…
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Life is Mostly About Landing Tricks
Do you do all of your own stunts? For some (James), life is mostly about hitting sequences and mastering combos; for others (me), putting down moves plays a less significant role. On this week's episode, James and I dissect the importance of landing tricks. Then we get into the good, the bad, and...
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State Sanctioned Diabetes
Sometimes your cat will be diagnosed with diabetes because he was addicted to getting UTIs so the emergency vet had to inject him with steroids that cause the pancreas to act up which will ultimately cost you ten thousand dollars!!! This episode is basically a PSA to get the pet insurance btw!!!...
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Finding Our Zen or Whatever
The secret to finding your zen? Perhaps it's going off the grid to fish on some remote lake in the middle of Canada, cracking a cold one and watching the storms roll through, or picking off your moles one by one — who am I to judge? Drue and I take to the podcast to workshop the concept of...
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We're Off the Stuff
You know what's chic? Cutting back, scaling down, doing sort of a less is more moment. In reference to what exactly? Well, anything that's no longer serving you, of course! On this week's episode, Jeremy and I dive into what we're saying no to, including carbonated beverages, aluminum-free...
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We've Been to the Year 3000
POV: It's 2006, the Jonas Brothers have just released their debut album, It's About Time, and you briefly leave your body. Caroline and I get into her music origin story, her earliest fandoms, and how that eventually led to building the Chicago Show Calendar. Then we get into the Good, the Bad…
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It's Really Hard to Be Alive
Have you ever had to do a few laps around Agora Market before working up the courage to ask the guy behind the deli counter for a pound of pork chorizo? Because for some of us, that's just a Thursday! Martina and I spend this week's episode mostly agreeing that it's actually really hard to be...
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Can I Interest You in a Glass of Milk?
Milk with dinner is a Midwestern birthright, and the internet has a lot of feelings about it. Whether you've kept the faith, developed a tragic intolerance, or just quietly renounced your heritage, Sophia and I weigh in on this week's episode. Then it's time for The Good, The Bad & The Ugly: the...
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U-Haul
Listen, we're going to let you in on a little secret — if you ever find yourself stuck somewhere and there are no rental cars available, you're going to get your ass over to the nearest U-Haul and take it from there, okay? Donnie and I hop on the podcast to swap survivor skills and Survivor 50…
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A New Bombshell Has Entered the Villa
POV: I interrupt your sunbathing to ask if I can pull you for a chat, but I'm a sexy banana named Benanito, wyd? Greg and I take to the podcast to dissect the AI-generated, fruit-themed Love Island mini-series that has taken TikTok by storm. Then we dive into The Good, The Bad & The Ugly…
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To Be Cringe Is to Be Free
Unfortunately whoever said, "If a thing is worth doing, it is worth doing badly" was onto something. Post your first attempt at a french mani to main, publish the scripted podcast episode you recorded out of your studio apartment, to be cringe is to be free! Alex and I jump on the podcast to talk...
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Mint and Chocolate
When it comes to sweets, what's your preferred flavor profile? There is a right and wrong answer, btw! If you gravitate toward fruity desserts, you're officially in the doghouse. I don't make the rules! If, like me, you yearn for rich, chocolatey confections, congratulations, you've been marked...
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Reality TV Pilled
Who needs fictionalized drama when you have the service industry? There's no group more ripe with scandal than the front-of-house staff at your favorite local haunt. Sophia and I take to the podcast to celebrate reality TV's greatest hits, including the likes of Vanderpump Rules and Southern...
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The Best Places to Cry on Campus
College was a fever dream, a bunch of kids living in a pretend world, cosplaying as adults with meal plans, and it was awesome!!! Mickey and I jump on the podcast to chat about our freshman year floor (s/o Sellery 7A), navigating co-ed living and communal bathrooms, and the best places to cry on...
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A Pink Lamborghini
Are you ready to level up your dating game? Looking to impress some lucky lady? The Rizzler says the key to winning her heart is actually quite simple, head to your local mall and buy her a pink Lamborghini, duh!!! Conor and I take to the podcast to celebrate his 30th with a little help from the...
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Stuff vs. Things
What constitutes stuff vs. things? Easy, boys like stuff, girls like things, and a dream is a wish the heart makes, next question! Meghan and I take to the podcast to settle the stuff vs. things debate, defend the typo, survive a smelly Uber, and drag the completely vibeless CVS on Chicago Ave....
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Celebrity Thinkpiece
Your favorite celebrity is planning their next thinkpiece on Substack, whether you like it or not! Superstars, they're just like us. James and I jump on the podcast to praise the tactile joy of writing with pen and paper, mock the tired cliché of movies that begin at the sound of an alarm clock,...
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Is This Thing On?
Where do I begin? It’s been exactly eight months since I’ve blasted your eardrums with my microphone, and so many things have changed in such a short period of time. Some good, and some catastrophically bad, but of course, I don’t need to tell you that, just look outside!!! On the personal front…
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Bring Back Crossover Episodes
Picture this: the year is 2006, and Disney's three-episode crossover series 'That's So Suite Life of Hannah Montana' is releasing its first episode at 8/7 central, and you're SAT, ready to witness a piece of history. James and I take to the podcast to nerd out over iconic crossover episodes…
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We’re All Afraid Our Kids Will Be Losers
We're all secretly afraid that our kids will be losers, and listen, I'm here to tell you that if that happened to me? I wouldn't talk to him either! James and I jump on the podcast to toast to bar games (think pool, darts, shuffleboard, yktv!!!), lament the fact that our thousand-dollar pocket...
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The Breakfast Industrial Complex
Why did breakfast box itself into such narrow thinking? The day's most important meal could be so much more than eggs, if only we let it become fully realized!!! Sadie and I jump on the podcast to chat about nicknames we love, bike lanes we loathe, and our deep dissatisfaction with the oppressive...
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Novelty Snacks
If there's a viral snack collab unfolding, Lilly is on the scene! Mountain Dew x Flamin’ Hot Cheetos? Sign her up. Swedish Fish Oreos? She's buying 'em, and nobody can stop her, damn it! Lilly and I take to the podcast to indulge in absurd snack innovations, spiral about accumulating too much...
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A Biggie for Your Troubles
Who eats sardines straight from the tin, carries a wad of rubberband-bound singles, and is in “talks” with the Italian government? Depends on who's asking. Adam and I take to the podcast to toast to tinned fish, raise a stink about early morning construction, and pour one out for the many folks…
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Sexy Unique Restaurant
It’s important to remember that the SUR experience has little to do with the food. Its true specialties lie in campy ambiance, overpriced cocktails, and the chance to share a room with some of reality TV’s messiest players—pure bliss! Matt and I jump on the podcast to honor our favorite divorce...
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The Waterpark Capital of the World
Picture this: You're freshly thirteen, you've got your brand new Ocean Pacific swimsuit on, and you're patiently making your way up the wooden staircase with your tube in hand. What's waiting for you at the top, you ask? None other than the Wilderness' most infamous waterslide, the Hurricane.…
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Wrestling Is the Straight Man’s Drag
Name something more c*nty than a giant chiseled man with a spray tan and platinum blonde blowout strutting to the ring in a bedazzled outfit to the tune of "Real American"—you can't! Rohan and I take to the podcast to celebrate grown men finding an outlet for self-expression, reject the creation…
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Just Scan the QR Code on the Table
If I have to use my own cellphone to pull up the menu at the restaurant, I'm clocking in because I work here now. I said what I said! James and I return to the podcast to celebrate Flow's Academy Award for Best Animated Feature (s/o to Latvia, a real place that exists!), dismantle the Digital…
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Feeling Insecure About My Water Bottle
I recently found myself feeling insecure about my Hydro during a Zoom call full of Stanleys and decided enough is enough! Screw your trendy water bottle! Unless you're still chewing on your Camelbak straw, like seriously, it's time to move on. James and I hit the podcast to celebrate mixing…
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Leaving It All on the Field
Picture this: The year is 2025 and you're making the active choice to jump back on the reading train after it dawns on you that you've forgotten how to do anything besides watch TV. Sound familiar? If so, you're safe here! Grace and I take to the podcast to celebrate Chelsea Handler's new book,...
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Seafood Boil Mukbang
Have you ever been out to eat when your waiter suddenly goes missing, only to reappear on stage, mic in hand, bringing down the house? It's like, sure you wanted another martini, but ultimately you're happy they're having their moment! Owen and I take to the podcast to celebrate servers with…
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Gleek Hive Rise Up
Were you normal, or were you spending your iTunes gift cards on Glee covers? Don't worry, you're amongst friends! Donnie and I take to the podcast to celebrate authenticity, stress over our favorite strategy-based reality TV game shows, and complain about men, naturally! Btw, did we ever figure…
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Breakfast Is Thrust Upon You
Brunch is something you plan in advance. It's an event you prepare for. Heck, you might even put on a cute outfit! Breakfast, on the other hand, is thrust upon you (whether you like it or not!) Luke and I take to the podcast to rejoice in the pleasure of breakfast with your friends, complain…
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Death of the Mainstream
Everyone can be someone and anything can be cool — and isn't that beautiful? Sure, there will always be pop stars with seismic fanbases like Taylor Swift and Beyoncé, but the "mainstream" is over, you heard it here first! James and I take to the podcast to dive into the death of the mainstream,...
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When Your Pants Get a Little Loose at the Knees
We're back, babies! And ever so grateful to be back in your ears each week. We missed you terribly — what a long two months it has truly been. Much to catch up on, so let's take it from the top! James and I take to the podcast to share our favorite onomatopoeias, lament over the humiliation of...
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You Seem Tired
Friendly reminder that the absolute worst thing you can do is tell someone they seem tired, it never goes over well. Instead, you could try, "You look like shit," or "What the hell is your problem." This week James and I take to the podcast to encourage more themed parties, commiserate about just...
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Becoming a Better Person
Great news team, becoming a better person is actually incredibly easy! Follow our 5-step process and you'll surely go straight to heaven or be reincarnated as something really cool or whatever. In this week's episode, James and I take to the podcast to celebrate the versatility of the fist bump,...
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What’s up with Delaware?
Have you ever been to the state of Delaware? Because me neither, and I have no designs on visiting! Devonte and I take to the podcast to celebrate finding fulfillment in our respective careers and shared community, to burst the bubble that is traveling for work, and to throw shade at the CTA....
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Weaponized Incompetence
Playing dumb is all fun and games until you're on the receiving end of such behavior — we said what we said! Aidan and I take to the podcast to sing the praises of our favorite fast-food chain (Taco Bell, duh!), deliberate over the appropriate way to deplane after a flight, and expose people for...
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The Quest to Become a Morning Person
Are you buying into the propaganda that morning people are more productive? Because we’ve sold our souls and signed on the dotted line. Manu and I are just a couple of night owls on the quest to become early risers and get that damn worm if it's the last thing we do! Join us on the podcast for a...
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What Your Cracked iPhone Says About You
If you listen to this episode I'm sorry and if you make it all the way to the end something is literally wrong with you! Truly rubbing my last two brain cells together for this one, enter at your own risk! James and I take to the podcast to relive the golden age of computer games, lament the…
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We're Not Friends We're Business Partners
We're starting a support group for people who have had to execute a Facebook Marketplace pickup while viciously hungover—do you want in? Luke and I take to the podcast this week to chat about our favorite micro-influencers, our aversion to submitting maintenance requests as renters, and our deep...
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Concert Etiquette
If it's one thing about us, it's that we're going to buy tickets to the concert! Annie and I take to the podcast to share in our love for being "woo" girls at our favorite live shows, to bitch about music venues that don't have water stations, and to shame our friends who don't know how to…
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9 Beers, 9 Hotdogs, 9 Innings
How many hotdogs could you reasonably consume in a 2.5-hour sitting? The 9x9x9 challenge has officially met its match, and I have the absolute pleasure of hosting our fearless champion on this week's podcast! Neil and I take to the pod to chat about the joys of trying your hand at something new,...
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Autumn's Rebrand
Is it just us, or do all Midwestern dads have the same undeniable penchant for building elaborate underwater ecosystems within the home? What’s the story there? This week on the podcast Grace and I share our affinity for Autumn's rebrand, our loathing of overcrowded spaces, and our tendency…
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The Man Behind the Curtain
If you're chemically addicted to watching Chicago apartment tours on TikTok, this episode is for you! Get to know the man behind the curtain (or camera), from his least favorite household chore to his go-to Chipotle order. Dean and I take to the podcast to chat about how he got started doing his...
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ABOUT THIS SHOW
Welcome to Pessimistic at Best, a podcast for those with a penchant for frequent frustrations, personal gripes, unpopular opinions, honest observations, and the like. Hosted by Sam, your resident Pessimistic Patty, this weekly show operates on the belief that no complaint is too small.
Each week, Sam sits down with a guest to explore the good, the bad, and the ugly. A surprisingly good country album by your favorite pop artist, a bad bang trim you gave yourself during a manic episode, a military homecoming video on the internet that made you ugly cry. The list is endless, and therein lies the beauty. Come on in, we saved you a seat!
HOSTED BY
Sam Georgson
CATEGORIES
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Frequently Asked Questions
How many episodes does Pessimistic at Best have?
Pessimistic at Best currently has 187 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Pessimistic at Best about?
Welcome to Pessimistic at Best, a podcast for those with a penchant for frequent frustrations, personal gripes, unpopular opinions, honest observations, and the like. Hosted by Sam, your resident Pessimistic Patty, this weekly show operates on the belief that no complaint is too small. Each week,...
How often does Pessimistic at Best release new episodes?
Pessimistic at Best publishes regularly with 187 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Pessimistic at Best?
You can listen to Pessimistic at Best on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Pessimistic at Best?
Pessimistic at Best is created and hosted by Sam Georgson.
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