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.

Featuring a lineup of top-tier comedians, we'll dive into everything that makes the holidays hilarious: the gift-giving disasters, the over-the-top decorations, the questionable New Year's resolutions, and, of course, the post-Christmas letdown.

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.

Featuring a lineup of top-tier comedians, we'll dive into everything that makes the holidays hilarious: the gift-giving disasters, the over-the-top decorations, the questionable New Year's resolutions, and, of course, the post-Christmas letdown.

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!

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.

Featuring a lineup of top-tier comedians, we'll dive into everything that makes the holidays hilarious: the gift-giving disasters, the over-the-top decorations, the questionable New Year's resolutions, and, of course, the post-Christmas letdown.

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!

Looking for a fun way to spend Valentine’s Day? Whether you’re part of a couple, single, or hanging with friends, join us for an evening of laughter and love at the Hyatt in Cambridge!

Make it a full night out with our dinner package, pairing gourmet dining with top-tier comedy.

Whether you’re single, taken, or somewhere in between, Cupid & Comedy promises a night of laughter that will warm your heart! Bring your friends, your date, or come solo for a night of hilarity that’s sure to make this Valentine’s Day one to remember.

Don’t miss out on the love and laughs! Grab your tickets now!

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.

Featuring a lineup of top-tier comedians, we'll dive into everything that makes the holidays hilarious: the gift-giving disasters, the over-the-top decorations, the questionable New Year's resolutions, and, of course, the post-Christmas letdown.

The Comedy Studio has long been the launchpad for fresh talent, sending comedians to national stages and beyond. Now, with the help of The Boston Comedy Festival, we’re taking things to the next level! Catch a lineup of Boston’s and beyond’s rising stars—future headliners delivering a night of unforgettable laughs. You’ll see comics who’ve appeared on HBO, Netflix, late-night TV, and more right before they blow up. Expect edgy, off-the-wall humor, a dash of raunch with unexpected twists, and razor-sharp takes on the chaos of modern attitudes. Millennials and Gen Z love it for a reason—this is comedy that hits where it counts. You never know who may drop in. Co-presented by The Boston Comedy Festival!

Amy’s debut album Solid Gold is available on Kill Rock Stars, and was named one of the top 10 comedy albums of 2016 by The Interrobang. You may have also seen Amy on Viceland or heard her on Sirius XM, NPR, Doug Loves Movies, The Adam Carolla Show, The Bennington Show, Put Your Hands Together, All Fantasy Everything, Keith and the Girl, or her own podcast “Who’s Your God?.” Amy is a nationally touring festival and comedy club headliner, and she has performed in the Moontower Comedy Festival, Bridgetown Comedy Fest, SxSW, the High Plains Comedy Fest, Laughing Skull, Big Sky, San Francisco Sketchfest, the Bumbershoot Festival and more.

Certified Fresh, hosted by Jack Hall, takes place Thursdays and showcases a dynamic mix of Boston’s emerging talent and seasoned comedians. Whether you’re discovering new faces or catching a set from someone on the verge of stardom, the night promises laughter from start to finish. With performances from both up-and-coming acts and Boston’s best comics, it’s the perfect way to enjoy guaranteed laughs and get a taste of the next big thing in comedy. This week’s show is co-presented by The Boston Comedy Festival!

Amy’s debut album Solid Gold is available on Kill Rock Stars, and was named one of the top 10 comedy albums of 2016 by The Interrobang. You may have also seen Amy on Viceland or heard her on Sirius XM, NPR, Doug Loves Movies, The Adam Carolla Show, The Bennington Show, Put Your Hands Together, All Fantasy Everything, Keith and the Girl, or her own podcast “Who’s Your God?.” Amy is a nationally touring festival and comedy club headliner, and she has performed in the Moontower Comedy Festival, Bridgetown Comedy Fest, SxSW, the High Plains Comedy Fest, Laughing Skull, Big Sky, San Francisco Sketchfest, the Bumbershoot Festival and more.

Amy Miller was one of Comedy Central’s “Up Next” comics, and has a brand new Half Hour Special called Ham Mouth on the Comedy Central YouTube channel. As a brand new comic she was a breakout favorite in the final season of Last Comic Standing. She has a half hour comedy special on Epix’s Unprotected Sets and her Comedy Central Presents set has been viewed over 3 million times on Youtube and Facebook. She was also a featured comic on Viceland’s Flophouse. On Last Comic Standing, Keenen Ivory Wayans said she had one of the “fiercest jokes he had ever heard.” Originally from the East Bay, Amy found her comedy chops in Oakland and is still a regular at the SF Punch Line and Cobb’s Comedy Club. Her material is personal, political, and 100% authentic. The Laugh Button says “She found a wildly creative way to find empowerment while simultaneously sparking laughter” and Courting Comedy says “Miller juxtaposes an unassuming demeanor with unflinching assurance.” After a move to Portland, Amy quickly rose to the top of the Pacific Northwest comedy scene, winning Portland’s Funniest in Helium’s 2015 contest, as well as being voted Portland’s Funniest Comedian for 2013 and 2015 in the Willamette Week. She was the first woman to win each position and the only one to win all three.

Amy’s debut album Solid Gold is available on Kill Rock Stars, and was named one of the top 10 comedy albums of 2016 by The Interrobang. You may have also seen Amy on Viceland or heard her on Sirius XM, NPR, Doug Loves Movies, The Adam Carolla Show, The Bennington Show, Put Your Hands Together, All Fantasy Everything, Keith and the Girl, or her own podcast “Who’s Your God?.” Amy is a nationally touring festival and comedy club headliner, and she has performed in the Moontower Comedy Festival, Bridgetown Comedy Fest, SxSW, the High Plains Comedy Fest, Laughing Skull, Big Sky, San Francisco Sketchfest, the Bumbershoot Festival and more.

Amy Miller was one of Comedy Central’s “Up Next” comics, and has a brand new Half Hour Special called Ham Mouth on the Comedy Central YouTube channel. As a brand new comic she was a breakout favorite in the final season of Last Comic Standing. She has a half hour comedy special on Epix’s Unprotected Sets and her Comedy Central Presents set has been viewed over 3 million times on Youtube and Facebook. She was also a featured comic on Viceland’s Flophouse. On Last Comic Standing, Keenen Ivory Wayans said she had one of the “fiercest jokes he had ever heard.” Originally from the East Bay, Amy found her comedy chops in Oakland and is still a regular at the SF Punch Line and Cobb’s Comedy Club. Her material is personal, political, and 100% authentic. The Laugh Button says “She found a wildly creative way to find empowerment while simultaneously sparking laughter” and Courting Comedy says “Miller juxtaposes an unassuming demeanor with unflinching assurance.” After a move to Portland, Amy quickly rose to the top of the Pacific Northwest comedy scene, winning Portland’s Funniest in Helium’s 2015 contest, as well as being voted Portland’s Funniest Comedian for 2013 and 2015 in the Willamette Week. She was the first woman to win each position and the only one to win all three.

Amy’s debut album Solid Gold is available on Kill Rock Stars, and was named one of the top 10 comedy albums of 2016 by The Interrobang. You may have also seen Amy on Viceland or heard her on Sirius XM, NPR, Doug Loves Movies, The Adam Carolla Show, The Bennington Show, Put Your Hands Together, All Fantasy Everything, Keith and the Girl, or her own podcast “Who’s Your God?.” Amy is a nationally touring festival and comedy club headliner, and she has performed in the Moontower Comedy Festival, Bridgetown Comedy Fest, SxSW, the High Plains Comedy Fest, Laughing Skull, Big Sky, San Francisco Sketchfest, the Bumbershoot Festival and more.