Broadway Director Tim Jackson Talks Tony-Nominated Musical

Summary

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Podcast Summary

Podcast: Bloomberg Talks
Episode: Broadway Director Talks His Tony-Nominated Musical
Date: June 1, 2026
Host: Emily Griffeo
Guests:

• Tim Jackson – Tony-nominated director & choreographer of Two Strangers Carry a Cake Across New York
• Chris Rouser – Editor at Large, Bloomberg Pursuits team

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Main Theme

This episode centers on Tim Jackson, the Tony Award-nominated director and choreographer behind the new hit Broadway musical Two Strangers Carry a Cake Across New York. Jackson discusses the show’s unconventional road to success, creative process, love letter to New York City, and the challenges and joys of making small-scale theater resonate on Broadway and beyond.

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Key Discussion Points & Insights

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1. Show Overview & Relatable Appeal

[00:30–01:09]

• Two Strangers Carry a Cake Across New York is a romantic comedy musical about a British man arriving in New York for his estranged father’s wedding, who is picked up by Robin, his soon-to-be stepsister. Together, they embark on an adventure through the city.
• The characters’ ordinariness is what makes the show widely relatable – “Dougal and Robin are seemingly quite ordinary people… then they’re thrown into this orbit with each other and have this wild 48 hours in New York together.” (Tim Jackson, 01:28–01:49)

Notable quote:

“The show’s a love letter to New York. My focus always was to make sure that they were having the most playful and fun and exciting adventure through the city.”
— Tim Jackson [01:50]

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2. The Show’s International Origins and Journey

[02:10–03:33]

• The musical’s creative team isn’t New York-based; it began in Ipswich and Northampton, UK.
• Jackson initially joined as dramaturg in 2018, helping writers Kit Buchan and Jim Barn develop the script through a series of workshops.
• The show traveled a winding path: regional UK theaters → Kiln Theatre (London, Off West End) → West End → Boston (where American actress Christiani Pitts joined as Robin) → Broadway.
• The casting of an American Robin helped open creative doors and add authenticity.

Notable moment:

“No one is a New Yorker in Two Strangers. We have made sure to involve as many Americans in the creation as possible... But a lot of the show is seeing New York through the perspective of an outsider.”
— Tim Jackson [03:33–04:02]

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3. Capturing the Essence of New York

[04:26–05:32]

• Jackson’s previous stint choreographing Merrily We Roll Along allowed him to spend significant time in NYC, soaking up neighborhoods like Flatbush and Chinatown and sharing location photos with the creative team to ensure authenticity.

Notable quote:

“I’ve been to Flatbush. I’ve walked the routes around Chinatown. I’ve experienced it as much as possible to try and make sure things were authentic.”
— Tim Jackson [05:12]

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4. Building Buzz and Breaking Through

[05:32–06:52]

• The show’s West End run was intentionally brief to facilitate a swift transfer to the US, partly thanks to UK cast album’s surprising popularity with American listeners.
• The opening number “New York” went viral, generating considerable buzz and demand.
• Early Broadway opening (well before Tonys season) proved advantageous, as the show built an audience organically.

Notable quote:

“The nicest thing is you can feel there’s a buzz, there’s a build in a buzz. We started off this show in tiny studio theaters which seat 30 people, and now we’re at the Longacre. So it’s an exciting evolution for the piece.”
— Tim Jackson [06:47–07:07]

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5. Touring and Accessibility

[07:07–08:35]

• North American tour scheduled for fall 2027.
• Jackson stresses his commitment to delivering a “best version” touring production, maintaining high standards for casting and design.
• Passionate about making theater for everyone, not just traditional Broadway audiences.

Notable moment:

“We want to connect with as many people as possible… I’m really passionate about making theater for anyone and everyone.”
— Tim Jackson [08:04–08:35]

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6. ‘Small but Mighty’ on Broadway

[08:35–09:51]

• The show has a small cast (two actors) but delivers a sense of scale and epicness on stage, thanks to design and movement.
• Set designer Sutra Gilmour’s ever-evolving set and double turntable create a dynamic, immersive experience.

Notable quote:

“Unanimously, it feels like when people leave, they were like, oh my gosh, it’s so much bigger than I thought it was going to be... The sort of connectivity between strangers bleeds into the auditorium and lifts the piece.”
— Tim Jackson [09:18–10:07]

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7. Recognition and the Tony Nominations

[10:27–11:48]

• Two Strangers earned eight Tony nominations, including Jackson’s first as a Broadway director.
• Jackson shares his emotional reaction—nervous for his collaborators, delighted and surprised for himself.
• He credits the entire team and expresses “I’m chuffed to bits” (UK for “thrilled”).

Notable moment:

“I watched the Tony awards from the UK on YouTube growing up… I didn't really think I would necessarily be part of that nominated gang. So I am, yeah, I’m chuffed to bits.”
— Tim Jackson [11:37–11:47]

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Memorable Quotes

• “The show’s a love letter to New York.” — Tim Jackson [01:50]
• “No one is a New Yorker in Two Strangers... But a lot of the show is seeing New York through the perspective of an outsider.” — Tim Jackson [03:33–04:02]
• “I’ve been to Flatbush. I’ve walked the routes around Chinatown... to make sure things were authentic.” — Tim Jackson [05:12]
• “We started off this show in tiny studio theaters which seat 30 people, and now we’re at the Longacre.” — Tim Jackson [06:47]
• “I’m really passionate about making theater for anyone and everyone.” — Tim Jackson [08:35]
• “It’s so much bigger than I thought it was going to be … connectivity between strangers bleeds into the auditorium.” — Tim Jackson [09:18–10:07]
• “I’m chuffed to bits.” — Tim Jackson [11:47]

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Timestamps for Key Segments

• Show Summary & Jackson’s Approach – [00:30–01:09]
• Show’s Origins & UK-to-Broadway Journey – [02:10–03:33]
• Authentically Portraying NYC – [04:26–05:32]
• Viral Success and Broadway Buzz – [05:32–06:52]
• Touring Plans & Inclusivity – [07:07–08:35]
• Scale and Stagecraft, Small but Mighty – [08:35–09:51]
• Tony Nominations & Reflections – [10:27–11:47]

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Tone & Atmosphere

The conversation is warm, celebratory, and effusive, mirroring the affectionate and optimistic spirit of the musical itself. Tim Jackson’s humility and team orientation are evident throughout, and there’s a palpable excitement around the production’s journey and Lynn’s potential impact on both Broadway and national audiences.

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For anyone curious about the heart behind Broadway’s latest Tony contender, this episode gives a thorough, heartfelt look at how a “small but mighty” romantic comedy is making a big mark in New York.

Transcript

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[Emily Griffeo]

We are going to Broadway. Kind of. We're like a few blocks from Broadway.

[Unidentified Cast Member (possibly a playful interjection)]

Throw some jazz hands.

[Tim Jackson]

Yes.

[Emily Griffeo]

All right. Emily Griffeo. Got it. We are speaking with the Tony Award nominated director and choreographer Tim Jackson, who's nominated for best director for Two Strangers Carry a Case Across a Cake Across New York. Tim directs better than I can read. And also with us is Chris Rouser from the Bloomberg Pursuits team, where he's editor at large. The romantic comedy follows a Brit who lands in New York for his estranged father's wedding. He's picked up by Robin, the sister of the bride. They have an adventure through New York City. Tim, did I get it right? Did I summarize it? Yeah, you did get it right.

[Tim Jackson]

Yeah, that's perfect.

And you haven't given too much away, so that's exciting.

[Emily Griffeo]

Okay, good, good. Well, first of all, congratulations on the nomination. That's really, really cool. The awards coming up this Sunday. Just talk to us a little bit about your approach in creating a musical that has such wide appeal.

[Tim Jackson]

Well, from the second I got the

script, I sort of knew it could have wide appeal appeal because the characters are so relatable. What's brilliant about the two of them is Dougal and Robin are seemingly quite ordinary people who are leading quite conventional lives, and then they're thrown into this orbit with each other and then have this wild 48 hours in New York together.

So, I mean, the show's a love

letter to New York. And so my focus always was to make sure that they were having the most playful and fun and exciting adventure through the city that they could. And with the two actors that we have, that's been very easy because they're so funny and so brilliant and, yeah, they bring a lot of joy, let's put it that way.

[Chris Rouser]

So the show is a love letter to New York, but it's not from New York. It started in Ipswich, in Northampton. Can you tell us the story of how you came to be a part of this show and where it originated?

[Tim Jackson]

Yeah, so I was brought on board in 2018 as a dramaturg. So I was brought on to help develop the writing and to work with

the two brilliant writers, Kit Buchan and Jim Barn, to sort of finesse it

and give it some shape. And then after about three workshops.

We were doing a sort of presentation, and the producer said, we feel like

maybe you are the right person to direct it. So at that point, I was brought

on to do these regional productions, and

then it's been on an epic journey. So we did it in these two

theatres that you've mentioned, and then we brought it to off West End to

a theatre called the Kiln Theatre.

And that's where Sam Tutty, who's now on Broadway, joined our process.

And then we took it to the West End, and then we took it to art in Boston, where we did

more rewrites on it. And we gained our Broadway leading lady, Christiane Pitts, who joined us there. And we did lots of.

And especially having an American woman play

the role of Robin, who is an American character, sort of opened up some doors for us.

And then, yeah, final few bits of

tweaks, and then we were on Broadway.

[Chris Rouser]

So no one is a New Yorker

[Tim Jackson]

in Two Strangers, no one is a New Yorker. We have all the way through, sort of made sure that we involve as

many Americans in their creation of it as possible. My husband is American, which is helpful. And, yeah, we've sort of made sure one of our producers is American. And so we've sort of been doing as much homework as we possibly could.

But a lot of the show is sort of seeing New York through the

perspective of an outsider. And so what's actually been really lovely about the response to the show is quite a lot of people have said who are native New Yorkers have been like, oh, this show's made me sort of re. Fall in love with New York again, because you sort of get to see it through those fresh eyes and feel the excitement of what it's like to arrive into the city for the first time and. And see all the secrets and treasures that are sort of hidden.

[Unidentified Cast Member (possibly a playful interjection)]

Tim, how did you approach, you know, doing homework, learning about kind of the essence of New York to fulfill this director role?

[Tim Jackson]

Well, I'd. I'd been very lucky that two years

ago I choreographed a musical on Broadway called Merrily Roll Along.

[Chris Rouser]

It did okay.

[Tim Jackson]

So I did all right.

Yeah, it did all right. Yeah. And so I'd. I got to be around for that for the duration of the show. And then I stayed in New York

for another six months after that. And so I really. I got sort of time to fully immerse myself, and I went to the different locations where the show was taking place because.

Because this other show, The Two Strangers,

had been in development since 2018. I already knew I was doing it.

I didn't necessarily think we'd get to

Broadway, but at the time I was like, well, I'm here, so I should make sure. I've been to Flatbush. I've walked the routes. I've walked the routes around China, Chinatown. I've sort of experienced it as much as possible to try and make sure things were authentic and took lots and lots of pictures to share with the writing team and the designers, et cetera.

[Chris Rouser]

So New York is notoriously tough, and that's partly what the show is about. But Broadway is notoriously tough, especially for a new musical. And you guys went from the West End to the US Pretty quickly. My understanding is you're. You had a pretty strictly limited run in the West End. Why come so quickly to the US when it is so dicey for new musicals?

[Tim Jackson]

Yeah, well, I'm glad that we did. And well done to our producers for making it happen, because it is brave, I think. We had recorded an album in the UK that had really caught fire and

lots of people were streaming it in America and we were able to see that there was an appetite in New York.

And we've since then recorded another album

with the Broadway cast and that's going bananas as well.

So I think we knew there was an appetite. And the song, the opening song of

the show, New York had, had gone

viral and we were getting a lot of love from America and people saying,

please bring it over, please bring it over.

So I think that it certainly is a risk for our producers, but one

that seems to be paying off so

far because I think a lot of shows open just before the Tonys, but

ours was open well, well before the end of last year. So we've sort of. We've been doing pretty good business, I think.

And the nicest thing is that you can feel that there's a buzz, There's

a build in a buzz. I feel like people are talking about the show more and more, which we're obviously thrilled about because we started off this show in tiny studio theaters which seat 30 people, and now we're at the Longacre. So it's an exciting evolution for the piece.

[Emily Griffeo]

We're speaking with Tim Jackson, the Tony Award nominated director and choreographer of Two Strangers Carry a Cake Across New York. Tim, the North American tour will start in fall of 2027, and I'm wondering about a couple things with regard to going from doing this in London to then doing this on Broadway and then taking it across North America on tour. Does the experience. Is the experience different or will it be different than somebody seeing it on Broadway?

[Tim Jackson]

I. I can't tell until we get there, I suppose. I mean, my intention is to make it as good as it can possibly

be, and I wouldn't want it to

be any lesser than watching a show on Broadway. I think there's something about seeing a

show come into your local theater that's really exciting because you sort of watch that space transform as another little gem arrives into it.

So I think that's exciting. I think we'll still be aiming for,

like, the most stellar casting and. And the. The elements will be the same, so the. The. You'll be seeing the best version of the show that we can have going around the country. So, yeah, that's certainly the intention. We're. We're so excited about the tour because we want to connect with as many people as possible, and we feel like it's a. It's a very relatable show for. For all of America. It's not just for. It's not aimed at Broadway audiences. It's aimed at every person. I'm really passionate about making theater for anyone and everyone.

[Chris Rouser]

It's also a small show, which makes it easier for it to transfer around the US for at the Tonys, you're up against some huge shows that were capitalized for three, four times as much as you guys spent to put the show together. How does it feel to be kind of like the small but mighty contender in that space?

[Tim Jackson]

It feels lovely. You know what's nice is that I think all the shows in the categories are quite individual and quite so discreet from each other. And therefore we just have to get

on and do our own thing.

I think it's nice you've described it

as small and mighty because I think

that is how we feel about. Has two characters in it. But unanimously, it feels like when people leave, they were like, oh, my gosh,

it's so much bigger than I thought it was going to be. And there's a feeling of scale and epicness.

I think Sutra Gilmour, who's our set

designer, who's also nominated for a Tony

Award, has done the most beautiful job

at creating a space that's sort of ever evolving. And we're on a double turntable, so it's always moving.

And especially towards the end of the

show, the visuals become bigger and bigger as we go through.

So I think the nice thing is

we feel like we're delivering in terms of scale and a sense of bigness,

I suppose, and people come out the other end of the show and they're like, oh, I sort of forgot it was only two people.

And I sort of felt like I'd

connected with everyone in the room. So I think the sort of connectivity

between strangers is something that sort of bleeds into the auditorium and sort of lifts the piece and.

Yeah, and it means you can't really

compare any of our shows in the different category. In their best musical category.

I think they are, they're really different

and I think they're all brilliant and. Yeah. So we just have to get on with it and just make sure that

what we're doing at the Long Aid

co is the best that we can make happen.

[Chris Rouser]

So two people on stage, eight Tony nominations. This is your first time directing on Broadway. Yes, yes. And your first time directing on Broadway. You are nominated for a Tony. How does that feel?

[Tim Jackson]

It feels wild.

It feels absolutely wild.

It feels so exciting. And do you know what? I was so nervous on the day of the nominations, but not for me. I just really wanted it for Kit

and Jim, the writers and I really

wanted it for Sam and Cristiani and everything else that came along is a

blessing and I'm very happy for such a. And Lux Pyramid, who's our orchestrator because I think he's done an amazing job.

But I just, I, I was just rooting for them. And so when that, when that news

came through, it was so exciting.

And then the, the fact that I

got a nomination too, I was surprised and delighted and I'm actually in rehearsals for another show at the moment. I'm doing this musical, something rotten in the UK and I had to go back into rehearsals after finding out and

sort of pretend like nothing had happened. But my brain was slightly elsewhere that afternoon. But yeah, I feel really proud and chuffed and I've, I watched the Tony awards from the UK on YouTube as

I was growing up and I was always very admiring of it but I didn't really think I would necessarily be part, part of that nominated gang. So I am, yeah, I'm chuffed a bit.

[Emily Griffeo]

Well, we are chuffed that you joined us here on Bloomberg Business Daily. So thank you so much for doing that and congratulations on the musical and on the nominations too. Tim Jackson, Tony Award nominated director and choreography of Two Strangers Carry a Cake Across New York. And our own award winning Chris Rouser from the Bloomberg Pursuits team. He is a theater aficionado and he. I'm always grateful when you join us on the program, Chris, so thank you, thank you for coming today.

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