Director Tim Jackson on Bringing 'Two Strangers (Carry a Cake Across New York)' to America

The plot of the musical "Two Strangers (Carry a Cake Across New York)" is broadly summed up by its title – it's about two strangers, about to become related through marriage, who carry a wedding cake across New York City. But it's also so much more than that: an examination of family, a meditation on the search for connection, and a sweet love story, of sorts, in which two people who don't quite fit in slowly find that they might fit with each other.

After a lengthy process of development, the play found its way to London's off-West End Kiln Theatre and, from there, to the Criterion Theatre in London's West End. Both productions were helmed by Tim Jackson, a choreographer-turned-director who has a deep history with the play, as well as extensive theater credits in Britain, on Broadway, and around the world. Now "Two Strangers" is landing at the American Repertory Theater for its American premiere.

A two-hander, "Two Strangers" creates a vibrant world through the chalk-and-cheese combination of Dougal (played by Sam Tutty, reprising the role after playing it both at the Kiln Theatre and in the West End, as well as on the Original London Cast recording) and Robin (American actor and singer Christiani Pitts). Dougal is the son of the groom, a man who abandoned him and his mother decades earlier and migrated to America where he became rich and successful. Dougal has dreamed all his life about meeting his father and now, on the occasion of his long-lost dad's wedding in New York City, that dream is about to come true. Childlike in his glee at just about everything, Dougal would be thrilled with his American adventure even if meeting his dad weren't in the cards.

Robin, on the other hand, is withdrawn to the point of sullenness, and far less happy about the occasion. The bride is her sister, just a few years older than her, which means that Dougal's dad is marrying someone young enough to be his daughter. Having grown up in Brooklyn, Robin is not impressed by the subway, the skyscrapers, or any of the tourist attractions that Dougal babbles about; she just wants to get through the next few days, carrying out the mundane tasks of fetching the wedding cake from the bakery and securing her sister new stockings to wear on the big day. Her lack of joy is rooted in friction between herself and her family: She's been estranged from her beloved grandmother for years, and there's palpable tension between her and her sister. (It's to the play's credit that we never meet any of these other people, yet they seem to fill space with the force of their narrative presence.)

The cake is a major plot point, but only one of many; from mundane details, a credit card-powered splurge that tears up the town, and a meet-cute mismatch that sparks to passionate life, this dynamic musical comedy unveils a wrenching story of wrongs, wounds, family schisms, and the enduring nature of hope.

EDGE caught up with Tim Jackson for a chat about the show, its development over time, and how the director sees it as a "Trojan horse" for its poignant message.

EDGE: You have a long history with "Two Strangers." Tell me a bit about it.

Tim Jackson: The play has gone through quite a lot of different versions over the years. The writers had the idea for the show back in 2000. They did a writing exercise in 2015, which is where the genesis of these two characters sprang from, and they really started work on it in 2017. I came on board in 2018. We did several workshops, and then we did productions at two regional theaters in the UK, Northampton and Ipswich. Then it came into off-West End at the Kiln Theater, then it went to the West End. So, it's gone through several different guises, but this opportunity arose and the producers grabbed it with eager hands.

EDGE: Have you had much input into how it's been developed and reshaped?

Tim Jackson: Yeah, very much. Even since we've been at the A.R.T., we've still been working on it and changing it. I've got a lovely relationship with the writers, Jim Barne and Kit Buchan, who I think the world of, and so we spent lots of time tinkering to try and make it a better script.

EDGE: How has the show changed over time?

Tim Jackson: When I came on board there were two or three songs, and we went through a huge amount of development together; now the show is very different. I actually was originally brought on as a dramaturg, and not the director, so the first two workshops I did, I was consulting on the script and songs and working in that respect, and then slowly, as they became more and more involved, that's when they asked me to direct, as well.

EDGE: Although the play is set in New York City, it's only been performed in England up until now. How well is it translating to an American theater?

Tim Jackson: So far, it feels great. We put a lot of energy into making sure that our room is full of people who live in New York, so we have lots of touch points to check in on, and there are some things that we've learned along the way, which is great. We've also tried to involve Americans all the way through the process, so we've had people come in and give us advice. I have an American agent, and we have producers who are American, and so I guess the American flavor is probably being tuned quicker and more directly now that we're here. But it's a lovely experience, and I'm absolutely loving being in Cambridge. It's fantastic.

EDGE: Sam Tutty, who played Dougal off-West End, is reprising the role for this run at the A.R.T. Did you make a point of bringing him over with you for this?

Tim Jackson: Yes, Sam is here, and he's doing a wonderful job. He's experiencing a lot of what the character Dougal experiences; he's really enjoying it, but he's now more aware of that distance, being further from home and being further from his mom, things like that.

EDGE: Boston is not quite New York City, but maybe that will give him a touch point as far as what it's like to be in a major American city.

Tim Jackson: Yes, exactly. It feels like [it's informing his performance] in a really lovely way. He has many characteristics that align with the character of Dougal. He's a bundle of joy.

EDGE: You've cast Christiani Pitts as Robin. She's an established actor and singer in her own right, so was she your top-of-mind person, or were you putting out your net fairly widely to find the right person?

Tim Jackson: We went through a casting process. Stephen Kopel brought us lots of different Robins, and we had quite an extensive audition process, and Christiani really seemed to sit in the version of Robin that I have in my head. She was extraordinary.

EDGE: As you've worked on this play through its various iterations, have you found yourself developing it more in terms of the rom-com aspect, or more in terms of the deeper questions of identity and family?

Tim Jackson: I think I've always leaned into the family and relationships side of things. I love comedy, and I think this show is one of the funniest things I've ever seen or read; I think that the writers have done an extraordinary job. I just want to make sure that these characters are fleshed out and three-dimensional, so we spent a lot of time during rehearsals talking through the script, really getting into the nitty gritty and fleshing out those characters.

I hope it feels light and fun and frothy and enjoyable, but hopefully those characters are robust enough that they might have a sort of Trojan horse element where you come away thinking about these people and their circumstances because they feel real to you and not like caricatures. The rom-com aspect is an easy way for people to get a sort of flavor of what the show might be, but I hope that once they arrive, they'll be experiencing a whole load of other things as well.

"Two Strangers (Carry a Cake Across New York)" runs May 20 – July 13 at the American Repertory Theater's Loeb Drama Center in Harvard Square, Cambridge, MA. For tickets and more information, follow this link. Check out the Original London Cast Recording at the major streaming platforms.