Comedy, Criticism, and Being a Good Guy While Playing the Villain with Jeff Dye | Ep 239 HTBITY

Jeff Dye sits down with me for a wide-ranging conversation about ambition, conviction, and what it actually means to stay true to yourself in modern comedy. We talk about why Jeff believes his goal is to be the best stand-up comedian possible, how that mindset shapes his choices, and what it’s like being perceived as the “bad guy” while still leading with honesty and goodwill. We also get into navigating public pressure, playing the heel intentionally, and why comedy sometimes eats its own — all without turning this into a pile-on or a hit piece. This is a thoughtful, candid conversation about identity, craft, and surviving the long game. ⸻⸻⸻⸻⸻ About Jeff Dye: Jeff Dye is a nationally touring stand-up comedian, actor, and host. He’s appeared multiple times on The Tonight Show with Jimmy Fallon, has his own Comedy Central Presents special, and has released two top-10 Billboard comedy albums, Dumb Is Gooder and Live From Madison, both currently playing on SiriusXM. He’s starred in NBC’s Better Late Than Never, appears regularly on Fox shows like The Masked Singer and I Can See Your Voice, and hosts the Fox game show Who the Bleep Is That?. Jeff is also a recurring guest on The Greg Gutfeld Show, known for delivering unfiltered takes with humor, conviction, and heart. Follow Jeff: Instagram: https://instagram.com/@jeffdye YouTube: https://www.youtube.com/c/jeffdye/ Website: http://www.jeffdye.com ⸻⸻⸻⸻⸻ Discussed in This Episode: 00:00 – Comedy convictions 03:45 – Clean vs edgy comedy 07:30 – Losing the filter 12:10 – Public pressure 17:55 – Sobriety & accountability 22:40 – Privacy vs publicity 27:30 – Wanting to be the best 31:45 – Texas, touring & home 36:30 – Playing the heel 41:50 – Comics turning on comics 47:20 – Forgiveness over revenge 53:10 – Being likable, staying honest 59:00 – The long game 01:05:30 – Final thoughts ⸻⸻⸻⸻⸻ Support the Pod 💥 Patreon: patreon.com/thejamiekennedy 🎟 Tour Dates: jamiekennedy.com 👕 Merch: https://jamiekennedy.c... 📺 Subscribe: https://www.youtube.com/@jamiekennedycomedy Learn more about your ad choices. Visit podcastchoices.com/adchoices