KT #770 - TOM SEGURA + SHERYL UNDERWOOD

This episode of Kill Tony is a wild, nonstop ride with guests Tom Segura and Cheryl Underwood—and a bunch of hilarious bucket picks that capture the show’s signature chaos.

The night starts with Tony Hinchcliffe’s high-energy intro, full of his trademark silliness, as a packed room of comedians gets ready to tear it up. The real standout moments come from the bucket picks. Dedrick Flynn nails it with sharp, relatable jokes about couch shopping. Then there’s Princess Rubber Ducky—who turns out to be a blind Catholic woman—who gets playfully roasted for her shocking religious material. It’s weird, it’s bold, and it’s pure Kill Tony.

Things keep getting stranger. Max tells a sex story that goes off the rails in the worst way. Nilo Mac delivers a confusing but oddly fascinating monologue about American advertising. And then come the bizarre interviews. One guy swears he was in a circus in Paris. Another, Stephen Glenn, claims he was a ‘90s child actor with an insane backstory involving Asian women and Mexican Mario. You won’t believe half of it.

The night wraps up with a killer set from Pat O’Neill, and a surprise appearance by Cheryl Underwood, who just finished taping a Netflix roast—and landed a special deal right after. It’s the perfect ending to a night that felt like pure, unfiltered comedy madness.