Crying in Chili's

Courtney Hill
  • 5.0 (2)
  • Careers

Welcome to Crying in Chili’s — the podcast for anyone currently experiencing a character-building season against their will. Hosted by Courtney Hill, this show dives into career chaos, layoffs, relationship drama, life pivots, bad decisions, quarter-life crises, and all the messy in-between moments that somehow become funny later. Equal parts vulnerable, witty, and unhinged in the most relatable way, Crying in Chili’s feels like debriefing life with your smartest and funniest friends over chips, salsa, and a Presidente Margarita. Expect honest conversations, plot twists, guest interviews, emotional support disguised as comedy, and reminders that nobody really has it figured out. Because sometimes rock bottom looks like a single tear falling into your Presidente Margarita.

Episodes

  1. 2d ago

    Episode 3: Rejection, Redirection & Buff Jesus

    Episode 3: Rejection, Redirection & Buff Jesus What do layoffs, comedy, job searching, and a ripped version of Jesus have in common? This week on Crying in Chili's, Courtney sits down with comedian, writer, and former coworker Anthony Cusumano to talk about rejection, redirection, and what happens when life forces you to rethink the path you thought you were on. From navigating layoffs and today's chaotic job market to pursuing creative dreams outside of corporate America, Anthony shares how he's balancing freelance work, comedy, and his latest creative project: Buff Jesus—a comedy short film about a conservative priest, a queer graffiti artist, and an unexpectedly effective piece of church marketing. Along the way, Courtney and Anthony swap interview horror stories, discuss why personality still matters in hiring, debate whether anyone actually enjoys Applebee's, and explore the idea that sometimes rejection isn't a dead end—it's simply redirection toward something better. Whether you're job hunting, chasing a creative dream, questioning your career path, or just here to find out why Buff Jesus exists, this episode is for you. In this episode: Navigating layoffs and career uncertaintyThe realities of today's job marketWhy rejection isn't always a bad thingRecruiter and interview horror storiesAnthony's original musicalThe story behind Buff JesusWhy Chili's will always beat Applebee's Guest: Anthony Cusumano Comedian, writer, performer, and creator based in Chicago. Follow Anthony on InstagramCheck out the first scene of Buff Jesus on Youtube!

    56 min

  2. May 29

    Episode 2: Do The Damn Thing

    Episode 2: Do The Damn Thing Courtney is joined by former coworker and creative powerhouse Amanda Duncan for a conversation about layoffs, burnout, freelancing, music, and figuring out who you are when your job title disappears. From corporate chaos to creative dreams, they discuss perfectionism, trusting your instincts, crying in public, and why sometimes the best plan is to stop waiting and just do the damn thing. Grab your chips and salsa. The emotional debrief is now in session. Connect with Amanda: Instagramhttps://amandaduncan.com/

    1h 10m

  3. May 22

    Episode 1: Q2 Chaos

    Most of us are just trying to survive the chaos — whether it’s a breakup, a layoff, or a broken foot — and somehow laugh through the mess. In the very first episode of Crying in Chili’s, Courtney and her forever bestie Vickie unpack the absolute rollercoaster that has been Courtney’s Q2 of 2026: losing her job, breaking her foot, moving apartments, spiraling over health insurance, and questioning if the universe has personally put her on a character-building subscription plan. Through laughter, emotional damage, and a few too many “you genuinely cannot make this up” moments, they talk about the reality of layoffs, the chaos of adulthood, Sabrina Carpenter, friendship, vulnerability, and why sometimes the only thing you can do is laugh before you cry again. If you’re tired of the polished version of adulthood and craving honest conversations with a side of humor, this episode is for you. Because sometimes rock bottom looks like a single tear falling into your Presidente Margarita.

    56 min
  • 3 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

Welcome to Crying in Chili’s — the podcast for anyone currently experiencing a character-building season against their will. Hosted by Courtney Hill, this show dives into career chaos, layoffs, relationship drama, life pivots, bad decisions, quarter-life crises, and all the messy in-between moments that somehow become funny later. Equal parts vulnerable, witty, and unhinged in the most relatable way, Crying in Chili’s feels like debriefing life with your smartest and funniest friends over chips, salsa, and a Presidente Margarita. Expect honest conversations, plot twists, guest interviews, emotional support disguised as comedy, and reminders that nobody really has it figured out. Because sometimes rock bottom looks like a single tear falling into your Presidente Margarita.

Information

  • Creator
    Courtney Hill
  • Years Active
    2K
  • Episodes
    3
  • Rating
    Explicit
  • Copyright
    © 2026 Courtney Hill
  • Show Website
    Crying in Chili's