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Nomination created on December 19, 2025

“They” streaming now on YT https://t.co/EFTDAsGlPK

A beautifully chaotic friendship on full display, where Bobby Lee and Andrew Santino turn every episode into a mix of unfiltered roasting, absurd bits, and unexpectedly real moments that sneak up on you. It’s equal parts childish and sharp, bouncing between total nonsense and oddly honest reflections on fame, relationships, and insecurity—usually in the same breath. The dynamic is the whole point: unpredictable, slightly unhinged, and fueled by the kind of chemistry you can’t fake, where the line between joking and genuine emotion is always just a little blurry.
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Big Jay Oakerson Has Been Doing This Long Enough to Know Better
Jay's been a stand-up for over two decades, came up through the Philly and New York club scenes, and has the war stories to prove it. The interesting angle for Bad Friends is the gap between the road-dog veteran and the guy who's now sober-ish and doing a podcast empire. Ask him what the version of himself from 2005 would say about his life now.
What Do You Actually Owe Your Audience?
Jay has a loyal fan base that expects a certain level of unfiltered honesty and offensiveness. There's a real question underneath the jokes about where the line is between giving people what they came for and doing something you'll regret. Worth pushing him on whether he's ever crossed a line he wishes he hadn't.
Who's the Best Comic You've Ever Watched Destroy a Room?
A good prompt for stories and for genuine admiration. Jay has seen a lot of great comics up close. Getting him to talk about specific performances rather than generalities will pull out better material than asking about influences in the abstract.