I recently interviewed Alex Webb, playwright and musical director of Café Society Swing, currently in its final week at 59E59 Theaters. Webb, an Englishman, skillfully transformed the story of New York businessman Barney Josephson and his beloved jazz nightclub, Café Society, into a singularly entertaining show. The play, based on Josephson’s memoir, Cafe Society: The wrong place for the right people, tells the story of the club that launched the careers of Billie Holiday, Lena Horne, Sarah Vaughan, Big Joe Turner, Count Basie, Zero Mostel, Sid Caesar and Carol Channing and features an eight-piece jazz band and three singers.

I admit, I didn’t know much about Café Society before seeing the show and it’s really fascinating. Why do you think all these talented musicians flocked to Josephson and his club?

Part of it is, when you get cultural explosions or really amazing things happen, you often find that in music certain things happen in certain cities at certain times, and you get certain groups of musicians together and they do something. As much as we can understand it, it’s several things that you notice. One is that Barney Josephson was part of a particular current of thought in America. You have the idealism that many children of Jewish immigrants had about socialism, which was in the air in Britain, Europe and America at that time. Therefore, you had the idea of equality of everyone and all races. So you have that great idealism, which was probably more common than it is now. You have the Roosevelt era, where the Left was much more significant in America than it is now, and people could wear their hearts on their sleeves without being shot down as liberals. So the time was right to make a stand. That doesn’t mean it was easy; it was very difficult and courageous, but the moment was there.

Now, the other thing happening was that in the early years of the 20th century, you have this movement of African Americans to the northern cities, and you get this incredible culture, for example the Harlem Renaissance. And you get this fantastic boom in jazz music in the 20s and 30s. That was what all those musicians grew up through and they were ready to roll just at the time when he was opening his club. And the two things came together because Barney was a jazz lover, and he made it clear that they would play to a mixed audience, which was so necessary at the time. Black musicians still had to go through terrible ordeals. Billie Holiday toured with Count Basie and had to “black out,” she was so light-skinned, in case people thought she was a white singer singing with a black band; just one of the ridiculous things going on at the time. To really go to a club and be yourself and be supported, you can see why black artists would want to do that.

Tell me about the evolution of the show, from the 2011 Jazz Festival in London to its current run at 59E59 Theaters?

Originally it was a one-night show in a modest-sized venue called the Purcell Room in London, with one character in period costume. We didn’t make a big attempt to create a whole theatrical production. But it went down so well that the following year, we had a chance to feature it in a small theatre in London called the Tricycle, which is a bit like 59E59 in fact, a similar size. That’s when we knew we had something. Then it continued to evolve and then we tried to just make it a bit stronger dramaturgically. The music was pretty good but then we came up with this idea of inventing the characters to tell the story from different angles: the post-war yellow journalist who is out to get the club, and then of course the bartender who is on the side of the club and getting the story from the inside. That’s a difficult job for our actors to pull off, but on the other hand I think you give a little more information away that way. Hopefully, we keep the pace going with the music.

The pacing, I thought, was excellent. It definitely kept my attention and helped draw me into the story. Considering that the show is set in New York and is about such an historical moment in the city, do you find that New York audiences differ much from London audiences?

I was a bit unprepared to be honest, because I’m taking a New York jazz show to New York and I could get it quite wrong. But the reaction was really good. As to audiences being different, I think American audiences are warmer when warmed, so I’ve noticed we worked hard in the early parts of the show to give the feeling back to the audience. That’s fine, that’s what our job is. And at some point at the end, they’re really loving it, the way the music builds toward the end. We try to create a real sense of climax. That’s how it should be. I think by the end of this run, perhaps I’ll know more about the differences between those audiences. I think New York and London audiences are similar, they’re not necessarily easy to please, and they’re quite demanding. Having said that, I’ve had such lovely comments after the show. People really enjoy the show but are also really glad that the story is being told.

How involved was Terry Trilling-Josephson, Barney Josephson’s widow and co-author of the book that the play is based on, in the process of building the show?

She was a really important inspiration early on because, at the beginning, I didn’t have much information. She was a lovely woman, she was very encouraging, and she was pleased that someone had noticed the story. She tried and is still trying to get more attention to the story in other art forms and media. I wish her luck with that. As the story has evolved with the director, Simon Green, and myself, we’ve taken away the chronological narrative, which is a book, and tried to create the characters to tell the story in a more theatrical way. Along the way, we’ve found some other historical evidence. For example, thanks to Google, we found original newspapers from the time, with the columnists actually writing these very critical columns with innuendos about Communists, and that’s really interesting to get a flavor of the time. Also, I read more broadly about the Red Scare period. It was a fascinating time to be in America.

How long did the process take?

I wrote it quite quickly in 2011. We put it on again in 2012 and again in 2013 and again this year. By the time we got to it this year, we had radically changed the way we told the story. That was in June this year, and at that point I thought, “Okay, this could work in New York.” We were always refining it, even in the last couple of weeks in terms of certain lines. We had an English actor in New York, and what would happen is a New Yorker would say, “Oh that sentence didn’t feel quite right,” or “Can I suggest this slang word.” I can’t get that stuff as an Englishman without talking to a New Yorker. Some were small but it was significant because it’s about suspension of disbelief. It only takes one wrong piece of slang and you can lose the audience.

I was actually really struck by that, because I’m a New Yorker myself, I was really struck by how real the speech was and how non-British it was. It was very New York sounding, very authentic sounding.

I submerged myself in a lot of Raymond Chandler and film noir dialogue. I picked up some of that and tried to get some of that snappy kind of corny journalese. I tried to get the flavor of that right. Hopefully, I did.

Yes, I definitely think you did. How was collaborating with director Simon Green and have you ever worked together before?

No. It’s the first time I’ve worked with a proper theatre director. I’ve done other words with music shows, which tend to be simpler, a bit like the original version of this show. I’ve done things like tributes to great jazz musicians like Charlie Parker. So I think I’ve got some ability to put words and music together. What I was naïve about and what Simon was so helpful with was actually making it work as theater, and really interrogating my script. He’s very constructive in his criticism and that was really a great education for me. Simon is not only a director but he’s an actor and singer in musical theatre, so he’s really got the right grounding. And he loves jazz. Who knows, we might work together again.

You didn’t just write the play; you’re also the musical director and play piano in the show. What were some of the joys or challenges you faced juggling these different hats, perhaps during rehearsals or at any point during the run?

Getting the arrangements right was difficult in itself because we had so many styles of music, and one of the lovely things about Café Society was it went from folk songs to French chansons to swing to blues and so on. I’m trying to get the sound right. There’s a couple of numbers where we try to imitate the big band sound, like Count Basie had, with the horns. You try to get as big a sound as you can. I think that worked out pretty well. I spent a lot of time on the arrangements and revising them and revising them again and we’re nearly there. In terms of the wearing of different hats, it hasn’t been a problem. In rehearsal, what naturally happens is that Simon looks after the theatrical aspects and I the music. So we kind of stay out of each other’s way. That’s worked pretty well. We’re both easygoing guys, we both have a really good idea of what we’re going for.

In a broader sense, the musicians have been interested that I can also write a script. They find that unusual. The musicians here in New York, most of them are African Americans, and I think only one of them actually knew the story of Café Society. They’ve been so interested in it. I think they’re actually a little taken aback that an Englishman’s come over and brought this story and it’s a story that resonates with them, all the musicians, not just the black ones. So the fact that I’ve done all these things makes me a curiosity. (Laughs) But it hasn’t been a problem.

How did your own musical background influence you while writing the show? What did you draw from most, the music or the book?

I actually wrote some tunes for the show, and that was actually driven by necessity. For example, although I researched as far as I could the kind of songs that were played at the time, there are certain songs associated with artists. If you’re going to do Lena Horne, you’ve got to do “Stormy Weather.” But what I found was that I didn’t have a swing number. So I had to write something with that kind of medium swing feel. And then I wrote “Boogie Woogie Blues,” with different sections of boogie woogie with a swing band and the blues lyrics. That was supposed to let on what was going on at the time, those boogie woogie players like Big Joe Turner. So really writing was a problem solving exercise. I’ve got a gap here; let me write something. I’m glad to say that went quite well. I immersed myself in the music. Hopefully, I’ve kind of pastiched that slightly whimsical play on words to fill in the gaps. My musical background is broad. I was a boy in the 60s, so the first thing I heard was the Beatles, and I still enjoy pop music, a lot of classical music, jazz. I would just concentrate on getting the style right.

I think you’ve done that quite well. Have you ever played or considered playing one of the principal roles?

No, I haven’t got much of a singing voice actually, so no. And why would I in the sense that, in Britain we had very good singers in the show, and in New York, I couldn’t actually have chosen any three better singers. Cyrille [Aimée], Charenee [Wade], and Allan [Harris] are absolutely the dream team, and they are all completely individualists, all distinct from each other. We have a French chanson and we have Cyrille to do it. It’s amazing how we have a song as difficult to carry off as “Strange Fruit” and we have Charenee to do it. We have “Lush Life” and we have the male baritone in Allan. It couldn’t be better. You wouldn’t want to hear me over those guys.

Yeah, I have to say I thought all three principal singers had distinctly unique and wonderful voices.  What is the future of “Café Society Swing” after its run at 59E59 ends?

We have to look at it financially; it’s a lot of people in the show and it’s quite expensive in terms of set design and costumes. You have to take it from a business point of view. And then we have to look at it from a practical point of view; I can’t always be coming over to America. The show has legs here. I might just find someone to be a musical director here. I hope the show has a life after this. I’m not sure necessarily it should get bigger. There’s something about the smaller venues, it allows it to be more authentic and more intimate. 59E59 is brilliant from that point of view. It’s exactly where I would have liked to play if I had the choice and here we are. So I’m really delighted; it’s really worked out well. So we’d want to find venues with some of those characteristics. I hope it has legs; I think it does. It’s hard to say what exactly will happen. Maybe we can do something with it in England.

What other projects are you working on?

I’m going to do a concert about the music of Billy Strayhorn, Duke Ellington’s right hand man, next year at a jazz festival. I’m hoping that some American artists will be involved with that in London, that’s because it’s the centenary of Billy Strayhorn next year. I’ve been in touch with the Billy Strayhorn estate. He had lots of famous works like “Take the A Train,” one of Duke Ellington’s songs, is actually his composition. He’s a very interesting figure. This [Café Society Swing] has been quite a big thing to do, so I’m not really rushing into the next thing.

Café Society Swing plays through January 4 at 59E59 Theaters.