The Hope & Anchor Comedy Night

The Hope & Anchor Comedy Night

Saturday, March 8th, 2025
$10 Cover
Show starts at 7:30pm

Make sure to Call the Hope & Anchor (815-633-2552) during normal business hours to get a Reservation of a Table. The Show Cover will be added to your Table Check for the Night.

Comics for the Night:

Host: Kat Diaz
Guest Feature: Carly Malison
Main Feature: Drew Flagge
Headliner: Ryan Mason

Comedian Bio’s for the Night:

Host Kat Diaz hails from the rough streets of Des Moines, Iowa, but has called Chicago home for the last 10 years. Her humor can be described as a dry piece of toast buttered with wordplay and served with physical act outs that make you wonder “CAN all Latinas dance? Kat has trained at The Second City and her credits include Laugh Factory, Den Theatre and the Latina Comedy Festival. She currently produces Mi Gente at the Lincoln Lodge.

Guest Feature Carly Malison’s comedy tackles the tough issue in today’s world. Not afraid of “going there” from embarrassing stories and takes on everyday life she has been called a “force too reckoned with.” Carly has earned a few credits for herself. Along with featuring and emceeing all around the midwest she has opened for the likes of Steve-O (Jackass), Chad Daniels, Steve Bryne, JJ Walker, and Trailer Trash Tammy just to name a few. Carly has also performed at the North Carolina Comedy Festival, the Cleveland comedy festival and the Milwaukee Comedy Festival where she was chosen to perform in the “Best of the Fest.” She is regularly featured at the Milwaukee Improv, The Laughing Tap and Zanies.

Main Feature Drew Flagge has no shame in embracing his West Allis roots. He has been doing stand-up in Milwaukee for 7 years but retreats home every night to put on his best pair of sweatpants. Growing up his favorite game to play was “Don’t Cry” which involved a big blue yoga ball, and it’s lead to a life of being the most “liberal” person at a blue-collar job and the most “conservative” person in a comedy scene. His comedy reflects the uncertainty of where he fits in, but his love of everything involving morally gray, garbage behavior… Currently he hosts an open mic at the High Note Karaoke Lounge in Milwaukee, and has been on the Cream City Comedy Fest and Milwaukee Comedy Fest, has opened for Mike Recine (the Sitdown Podcast/ Union Delegate album) Adam Friedland (Cum Town Podcast) the Mean Boys Podcast, Vicki Barbolak (America’s Got Talent) and Ryan O’Flanagan.

Headliner Ryan Mason isn’t just a favorite in the Milwaukee comedy scene—he’s a driving force who’s been shaping its comedic landscape for over a decade. With more than 10 years of stand-up experience, Ryan has shared the spotlight with SNL cast members, Oscar winners, and a diverse spectrum of comedians, each collaboration adding a new dimension to his craft. His storytelling is more than just performance; it’s like weaving a tapestry of humor and humanity, turning everyday moments into captivating narratives. Audiences don’t just laugh—they embark on a journey with him, riding the waves of his wit and returning time and again for the unique blend of insight and hilarity only he can provide.