Pessimistic at Best
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
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 relaxation, results pending.
Then it's time for The Good, The Bad & The Ugly: thunderstorm season, the quiet death of the multi-in...
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 deodorant, and then some.
Then it's time for The Good, The Bad & The Ugly: When the function involves karaoke, the o...
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, and the Ugly: Ditching Spotify and starting fresh on Qobuz, the way people undervalue small businesses, and music industry PR lite...
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 alive!!!
Then we dive into the Good, the Bad, and the Ugly: writing your affirmations by hand, working through an eBay addicti...
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 year of the Fire Horse, wedding gift culture, and people (read: losers) who don't dress up for themed parties.
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 hot takes.
Then we dive into the Good, the Bad, and the Ugly: Embracing your 30s with open arms, airline horror stories, and toxic ...
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: recycling old trends, DJ remixes at bars, and the delivery robots terrorizing the streets of Chicago.
THERE'S MORE WH...
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 about Doing the Thing™️, whatever that thing may be.
Then it's time for The Good, The Bad & The Ugly: embracing creati...
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 safe! James and I take to the podcast to dissect his disturbing take on all things sweet.
Then it's time for The Go...
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 Hospitality.
Then it's time for The Good, The Bad & The Ugly: stealing from big box grocery stores, letting your intrusive ...
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 campus.
Then it’s time for The Good, The Bad & The Ugly: getting your alderman involved, construction companies that have the audacity...
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 Rizzler himself, file a formal complaint about the Mariano's on Chicago Avenue for its complete disregard for the customer experience,...
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. Join in, you know you wanna!
THERE'S MORE WHERE THAT CAME FROM:
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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, and dive into James' deep hatred for pranks.
THERE'S MORE WHERE THAT CAME FROM:
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: I quit my job, canceled my Hulu subscription, transferred my Spotify music library over to Tidal, started a business (insane), went to the...
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, spiral over the sensation of an itch, and pick apart some truly cursed celebrity endorsements.
P.S. This marks the end ...
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 computers require protective gear just to survive, and side-eye parents who let their kids wear AirPods during family time.
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 egg agenda.
THERE'S MORE WHERE THAT CAME FROM:
FOLLOW THE PODCAST
Instagram: @pessimisticatbes
Facebook: ...
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 “stuff,” and express our utter disgust at some of the world’s most nauseating smells.
THERE'S MORE WHERE TH...
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 who were recently denied Italian citizenship thanks to the consulate's ever-changing rules. Join in, we just might make you an of...
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