Pessimistic at Best

Pessimistic at Best

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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...
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Episode List

The Best Places to Cry on Campus

Mar 3rd, 2026 8:00 AM

Send us a love letter (or hate mail, your choice!)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 to wake you up on Sundays, and rehashing the Glen Powell drama from our last episode (with Lenny Kravitz also catching a few strays)Get silly with us on social:FOLLOW THE PODCASTInstagram: @pessimisticatbestFacebook: @pessimisticatbestWebsite: pessimisticatbest.comFOLLOW SAMInstagram: @samgeorgsonTikTok: @samgeorgsonTwitter: @samgeorgsonYouTube: @samgeorgsonWebsite: samanthageorgson.comFOLLOW MICKEYInstagram: @mick_odonnellSupport the show

A Pink Lamborghini

Feb 24th, 2026 8:00 AM

Send us a love letter (or hate mail, your choice!)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, and surrender to the Tell Me Lies drama. Get silly with us on social:FOLLOW THE PODCASTInstagram: @pessimisticatbestFacebook: @pessimisticatbestWebsite: pessimisticatbest.comFOLLOW SAMInstagram: @samgeorgsonTikTok: @samgeorgsonTwitter: @samgeorgsonYouTube: @samgeorgsonWebsite: samanthageorgson.comFOLLOW CONORInstagram: @longliveconorSupport the show

Stuff vs. Things

Feb 17th, 2026 8:00 AM

Send us a love letter (or hate mail, your choice!)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!Get silly with us on social:FOLLOW THE PODCASTInstagram: @pessimisticatbestFacebook: @pessimisticatbestWebsite: pessimisticatbest.comFOLLOW SAMInstagram: @samgeorgsonTikTok: @samgeorgsonTwitter: @samgeorgsonYouTube: @samgeorgsonWebsite: samanthageorgson.comFOLLOW MEGHANInstagram: @meghan.kathrynSupport the show

Celebrity Thinkpiece

Feb 10th, 2026 8:00 AM

Send us a love letter (or hate mail, your choice!)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.Get silly with us on social:FOLLOW THE PODCASTInstagram: @pessimisticatbestFacebook: @pessimisticatbestWebsite: pessimisticatbest.comFOLLOW SAMANTHAInstagram: @samgeorgsonTikTok: @samgeorgsonTwitter: @samgeorgsonYouTube: @samgeorgsonWebsite: samanthageorgson.comFOLLOW JAMESInstagram: @daycatcher_TikTok: @daycatcherTwitter: @daycatcherYouTube: @daycatcherWebsite: daycatcher.netSupport the show

Is This Thing On?

Feb 3rd, 2026 8:00 AM

Send us a love letter (or hate mail, your choice!)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 cottage, and bought 3 new swimsuits. Watch out, world—here she comes!James and I take to our respective microphones this week to obsess over the new New York Times game, Crossplay, short-circuit over needlessly complicated passkeys (Google, seriously baby, what do you want from me!), and LOL at some of 2016's most regrettable trends.Get silly with us on social:FOLLOW THE PODCASTInstagram: @pessimisticatbestFacebook: @pessimisticatbestWebsite: pessimisticatbest.comFOLLOW SAMANTHAInstagram: @samgeorgsonTikTok: @samgeorgsonTwitter: @samgeorgsonYouTube: @samgeorgsonWebsite: samanthageorgson.comFOLLOW JAMESInstagram: @daycatcher_TikTok: @daycatcherTwitter: @daycatcherYouTube: @daycatcherWebsite: daycatcher.netSupport the show

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