For more than two decades, legendary Jamaican comedian Oliver Samuels has been a staple of live entertainment for Jamaicans living in and around Toronto, Canada. His productions have consistently drawn packed houses, with the first, third, and fourth shows of a typical weekend often selling out days in advance and only limited seats remaining for Saturday matinees.

Recognising both the demand for Samuels’ signature brand of comedy, and the opportunity to create a new Father’s Day tradition, Whirlwind Live Performances has brought his latest theatrical hit, Where Dere’s A Will, Dere’s A Criminal, to New York City for Father’s Day weekend 2026.

The production, which enjoyed tremendous success in Canada, opened on Friday, June 19 and runs through Sunday, June 21 at Jamaican Performing Arts Center in Jamaica, Queens.

Organisers hope the annual Father’s Day staging will establish Oliver Samuels as a fixture of New York City’s holiday weekend celebrations for years to come.

Widely regarded as Jamaica’s greatest comedian, Samuels’ ability to transform everyday situations into laugh-out-loud moments has earned him generations of loyal fans both at home and throughout the Diaspora. Bringing that legacy to New York City — a global capital of theatre and home to the world-famous Broadway district — makes this Father’s Day engagement particularly significant.

This year’s Father’s Day weekend carries even deeper meaning. The holiday coincides with Juneteenth celebrations, Caribbean Heritage Month, and Men’s Mental Health Month, creating a unique opportunity for families to come together in a spirit of celebration, reflection, and community.

Never one to shy away from finding humour in life’s realities, Samuels offered his own perspective on why fathers deserve their moment in the spotlight.

“Unnu look here, every year Mother’s Day special, restaurant pack, theatre pack, all church pack when the bad pickney go church with dem modda… but whappin to the puppa dem? Dem can carry out too. So mek sure me see the whole family come out this weekend to see this play Where Dere’s A Will, Dere’s A Criminal,” he said.

According to Samuels, the production delivers everything audiences have come to expect from his work.

“Where Dere’s A Will, Dere’s A Criminal is funny, it involves the audience, it is full of suspense, and it is a show for the entire family. You won’t want to miss this,” Samuels said.

Blending comedy, audience interaction, and unexpected twists, the play promises an evening of entertainment that appeals to multiple generations. Whether patrons are long-time fans who have followed Samuels’ career for decades or younger theatre-goers experiencing his work for the first time, the production offers a chance to celebrate family, culture, and laughter together.

As New Yorkers and visitors look for meaningful ways to spend Father’s Day weekend, Where Dere’s A Will, Dere’s A Criminal provides a reminder of the enduring power of live theatre and of an entertainer whose influence on Jamaican comedy remains unmatched.

— Shereita Grizzle