​$3,000 Pappy Van Winkle & Carl Ruiz Cries - Best Last Year f Radio

The episode opens with a series of quirky, surreal monologues and ad reads, including a testimonial from Charissa praising Shopify for her entrepreneurial success. The core of the episode centers on Carl Ruiz bringing a $3,000 bottle of 20-year-old Pappy Van Winkle bourbon to the studio, sparking a chaotic, emotionally charged, and wildly comedic discussion. The hosts mock the bourbon’s value, debate its expiration date, and hilariously speculate about a fictional heist involving the Van Winkle family. Carl becomes unexpectedly emotional when a caller asks about his father, leading to a raw, tearful moment that shocks the group. The hosts immediately deflect with jokes, calling Carl’s tears 'Santa Claus-level' and joking about bottling his tears. The conversation veers into deep territory—family, mortality, and living in the moment—before spiraling back into absurdity with debates over classic comedies, the worst movies ever made, and a bizarre story about a man who drives to Montreal and gets a zit on his back. The episode ends with a surreal, almost dreamlike segment about a fish that looks like a rock, culminating in a failed attempt to identify it on-screen. The tone is chaotic, emotionally volatile, and relentlessly comedic, blending absurdity with moments of genuine vulnerability.