City Winery Boston & Boston Comedy Festival Present: Comedy & Cabernet. The best in local comedy and wine! The Boston Comedy Festival has been decanting the best comedy shows in New England for over 20 years. You have seen these comedians on Drybar, HBO, Team Coco, Jimmy Kimmel Live, Comedy Central, and headlining your favorite club or theater.
Will Smalley Will Smalley is a purveyor of the silly-arts and a dude-lover extraordinaire. As an established LGBTQ+ voice in the comedy scene, Will is a former finalist in the Boston Comedy Festival and has been featured in the Bridgetown Comedy Festival in Portland, OR. In addition to being a mainstay at the major comedy clubs and colleges across the Northeast, Will serves as the announcer/producer for Old School Game Show at the Wilbur Theater.
Sara Poulin A small town comic with a silly world view, Sara Poulin brings her unique outlook to everyday life. With witty observations and a spunky attitude she’ll capture your heart and make you laugh.
Logan O'Brien Logan is a Boston based comedian who placed third out of one hundred comedians in Laugh Boston’s Massachusetts Funniest Person competition in 2019, and has worked with national headliners such as Big Jay Oakerson, Punkie Johnson, Shane Gillis, and more. He performs regularly at clubs such as the Comedy Connection, Laugh Boston, and Nick’s Comedy Stop. He also co-hosts a podcast, and writes, produces, and acts in online sketches with three other comedians under the name the “South Shore Boyz.”
Big D Born and raised in the streets of Boston, Big D didn't have an easy start in life. In fact, he was homeless when he first discovered his talent for comedy. But that didn't stop him from pursuing his dream, and he quickly became a rising star in the comedy world. Big D's humor is raw, real, and always hilarious. He draws inspiration from his own life experiences, including the passing of his beloved mother, who he credits as his biggest inspiration. His unique perspective on life as a black man in America is both eye-opening and side-splittingly funny. So if you're looking for a good time and a lot of laughs, look no further than Demetrius "Big D" Hullum. He's the comic that will have you rolling in the aisles and begging for more!
