Tim Jackson on TWO STRANGERS & Creating a Heartfelt Adventure

When director Tim Jackson first encountered the script for Two Strangers (Carry a Cake Across New York), he immediately recognized something special. “Back in 2018 I read the script and instantly fell in love,” Jackson recalls. At the time, he was brought on as a dramaturg to help develop the musical alongside writers Kit Buchan and Jim Barne. “I was not expecting to become the director. But as soon as I held those reins I was always dreaming big, because I knew it should stand alongside the bigger shows.”

Now, years later, that belief has been validated in spectacular fashion. Two Strangers (Carry a Cake Across New York) has earned eight Tony Award nominations, including a nomination for Jackson himself for Best Director of a Musical. For a creative making their Broadway directorial debut, it is the kind of recognition most artists only dream about. Yet Jackson remains focused less on the accolades themselves and more on what they represent.

“It feels wonderful because I believe in this show with my whole heart,” he says. “It was small but mighty. The heart was big, the characters were truthful, robust, and full of humanity, and the songs were absolute bangers.”

The show’s journey from beloved British import to Broadway awards contender has been swift, but Jackson has made a conscious effort to savor every moment. “At the nominee luncheon at the Rainbow Room the other day we all gathered for the first time and got our nominee certificates, and it did feel like a bit of a ‘life moment’ worth clocking,” he states. “When the show first arrived on Broadway, I definitely made a conscious effort to lean in to how exciting it all was, and not to take any moment for granted.”

There were moments, he admits, when the reality of what was happening felt almost surreal. “Multiple times I just stood outside the Longacre and stared at our marquee and thought ‘WHAT is happening?!’”

What makes Jackson’s achievement especially notable is that it comes from directing one of Broadway’s most deceptively ambitious productions. While Two Strangers (Carry a Cake Across New York) features just two performers, Jackson approached the show with the same scope and imagination one might bring to a much larger musical. “For Two Strangers, the intimacy and the intensity is already front-and-center,” he explains. “So my challenge was to make a show that could feel like an epic adventure through a city that never sleeps, with only two people. To keep the picture changing, to keep the characters on the move, to keep the audiences on their toes and always experiencing the unexpected.”

The result is a production that feels considerably larger than its cast size might suggest. In fact, one of Jackson’s favorite compliments from audience members speaks directly to that achievement. “My biggest thrill is when people say after watching Two Strangers that they forgot there weren’t more people in the show,” he emphasizes. “Or when they talk about how epic or breathtaking certain moments feel. For me, just because a show is ‘intimate’ it doesn’t have to feel ‘small.’”

That philosophy extends to every aspect of Jackson’s work. Ask him what defines his directing style and he quickly redirects attention away from himself and toward the audience’s experience. “My North Star tends to be delivering hard on heart and humanity,” he points out. “It excites me if an audience can see something of themselves onstage, and so I try to make the characters relatable and real.”

That commitment to emotional authenticity drives every creative decision he makes. “I’ll always be looking to excavate the emotional center of the work, as that will unlock the rest of the creative,” Jackson shares. “Even as a choreographer, steps never come before intention. I must know why someone is dancing or singing, what is the story.”

For Jackson, directing is not about spectacle for spectacle’s sake. Every design choice, every staging decision, and every moment of choreography must serve a larger emotional purpose. “My mission is always to tell the story in the most engaging, entertaining and emotionally stirring way,” he says. “I don’t go to the theatre to observe. I go to feel.”

That philosophy can be felt throughout Two Strangers (Carry a Cake Across New York), where laughter and heartbreak frequently exist side by side. It is also reflected in the painstaking attention to detail Jackson brings to his productions. “Everything on the stage is very intentional and has been put under the microscope,” he reveals. “From the delivery of a joke, to the timing of a distant car horn, to the speed that a snowflake falls.”

The latter became something of an obsession during the show’s development. “Everyone was very patient as I obsessed over snow and tried a million variations throughout tech and previews!” he says with a laugh.

Perhaps that level of care helps explain why audiences have responded so strongly to the production. Jackson speaks proudly about the moments when a carefully calibrated emotional beat lands exactly as intended. “When the whole room collectively gasps, or we hear sniffling where I wanted a gut-punch of empathy, or when a carefully crafted comic beat goes up like a rocket and people are doubled over laughing, I feel very proud of that.”

As awards season continues, Jackson remains grateful that the show’s success is something shared by the entire company. “It’s extra special that we got eight nominations, so the whole Two Strangers gang is sharing in it together,” he states. “We’re all really chuffed.”

Looking ahead, Jackson will reunite with Buchan and Barne on the new musical MONA LOSER, a collaboration built on nearly a decade of creative partnership. “There is a lot of respect and admiration between us,” he adds. “It all arises from clear, honest communication for the last eight years.”

But even as new projects emerge, the impact of Two Strangers (Carry a Cake Across New York) remains profound. After all, this is a show built on the simple idea that opening yourself up to another person can change your life. It is a message Jackson believes resonates now more than ever. “Our world is this beautiful kaleidoscope of humans,” he imparts. “If you open yourself up to connecting with a stranger, then maybe incredible adventures can come your way.”