INTERVIEW: Masters of Sex's Annaleigh Ashford Plays TV's Best Lesbian Prostitute

INTERVIEW: Masters of Sex's Annaleigh Ashford Plays TV's Best Lesbian Prostitute
Preston Max Allen

Triple threat Annaleigh Ashford has charmed us all. First, she took Broadway by storm originating a part in Legally Blonde: The Musical, playing Glinda in Wicked, and receiving a Tony nomination for her leading role in the smash hit Kinky Boots (to name only a few of her theatrical accomplishments). Now, after a three-episode arc in season one of Showtime's racy Masters of Sex as Betty DiMelloshe's returned for season two as a series regular, and not by coincidence. Ashford's honest, comical, and occasionally heart-breaking portrayal of a 1950s lesbian prostitute now married to a man and keeping a whole lot of secrets often steals the show, and watching her character struggle and grow has provided some favorite moments for the audience. With every episode comes more potentially dangerous revelations for Betty, including next week's appearance of her former lover Helen, played by Sarah Silverman. And while Masters of Sex fans are on the edge of their seats waiting for the outcome, Ashford's already wrapped filming on season 2 and is now starring in another show opening on Broadway this month.

Luckily, she spared a between-rehearsals lunch break to speak exclusively to Shewired, and now we're bigger fans than ever.

SheWired: Betty is certainly bringing a new side of LGBT representation to TV and has also become a total fan favorite. So much so that you were in three episodes of the first season, and now you’re a regular in season two. What was it like to get that news? 

Annaleigh Ashford: Well, as an actor, being a series regular on a great television show is always one of your dreams, so it was such a dream come true to me to be part of not only such an incredible show but to also be playing such a strong, interesting character. To get to do it every week is such a gift. There’s an exciting thing happening in our entertainment industry right now where television is so incredibly diverse and interesting and excellent, and it’s a really exciting time to be an actor. So I just can’t believe it. I couldn’t be more grateful and more overjoyed to be part of the show every week.

Your character brings most of the comic relief, and a lot of comic honesty in very serious situations. What have been some of your favorite moments to film in the show so far? 

I think one of the reasons that I got to come back was because Betty’s character was set up so clearly and so honestly in the pilot. In her first scene with Dr. Masters, she kind of spells it out and tells it like it is, and that’s a very rare occurrence for Dr. Masters. Not only does he not get advice from women, but he should never be getting advice from a hooker. But he listens to the advice, and he takes it, and from that moment on the relationship between Betty and Dr. Masters is complicated and interesting. I think that opens the door, not only for comedy, but for honesty for the women of that era and the women of the social status for that era. It’s so tricky to keep it honest and yet make it funny, because you still want to be in the world of the show, and the world of the show is more serious. And when I came back this year for season 2, in the second episode when I have to come and sit in Dr. Master’s office, I think the writers did such an incredible job. We really pick up that relationship where we left off, and I just sit in his office and do whatever I want. Kind of living by my own agenda. 


Already in season 2 there have been many reveals we didn’t even necessarily expect to come so quickly. In the last episode - I don’t want to spoil anything - but there was a big revelation about how your character and her husband Gene met. What has been the most exciting thing about getting to explore these parts of her you maybe didn’t know about going in?

You know, as an actor, we do our backstory and we create a history for each character that we play. Sometimes the character and story play out exactly as you had created, and sometimes it doesn’t always match. I think when it doesn’t match it’s even more exciting. It was so exciting to read how Gene actually first met Betty, and it was also heartbreaking. Every script you get is like Christmas, it’s like opening a present. And I was as shocked by some of the twist and turns as I think some of the audience will be. There ARE a few more coming. Betty is a woman who has so many secrets, and you can only keep them hidden for so long.

What kind of research did you do to play a lesbian prostitute in the 1950s?

I did as much research as I could about gay culture in the 1950s, but sadly there is not as much material because that was a hidden and secret world. There have always been communities of homosexual people no matter what era you’re in, and at that time in the ‘50s, because we were living in such a conservative culture, so many of those groups had to be hidden. There’s a magazine started by the Daughters of Bilitis called The Ladder - I believe the publication started either in late ‘50s or early ‘60s - but it’s the beginnings of a community of women who were like-minded, not only in their sexual taste but also in their cultural and political views, and it was a way for them to secretly, quietly explore that. I looked up as much as I could about that. And I find that I drew so much from images. You know, a picture’s worth a million words; not just a thousand words, a million words. I found a couple great images that inspired me of different women who were lesbians in that era. 


With The Masters of Sex Cast

In this Sunday’s episode of Masters of Sex we’ll be meeting Betty’s mysterious ex-lover Helen, who is played by Sarah Silverman. What was it like to work with her?

Sarah Silverman is one of our greatest comedians, especially of this generation, and I think one of the best of all time. She is such an innovator, and she’s not just funny, but honest and a brilliant artist. The reason that our favorite comedians are funny is because they’re honest, and I think she brings such a beautiful honesty in her work as an actress. It was such an honor and a privilege to be her scene partner and to play opposite of her, and then as a human she couldn’t be more warm and loving. And she is funny as hell. It was such a treat to play with her.

Masters of Sex has definitely blown up lately. Do you often get recognized as Betty?

It’s funny, we saw King Lear last night at Shakespeare in the Park and, like, three people stopped me and were like, “Oh we love Masters of Sex!” I think partly because my hair is so blonde right now, because we just finished filming this season, but when my hair goes back to its normal color people often don’t recognize me. I think because the character is so strong and so specific and so different from who I am as a person every day, people often don’t recognize me. But I’m so grateful that when they do they comment on how they’re such a fan of the show. 


Even though Masters of Sex takes place in the 50s, there are a lot of queer themes that carry over to today. Do you ever experience any fan encounters with people who relate to themes in the show?

Absolutely. The LGBT community is continuing to struggle every day.  We’re still fighting for equality in so many areas of our culture, our society, and our politics. I feel like, even though we’re looking at one woman’s story years ago in an era that’s so different from ours now, it’s still so relevant because we’re still fighting that fight. And then, in a bigger picture for the themes of the show, I think that sexuality is still an unspoken piece of our society that is still pushed into the corner and into the closet. Many people are increasingly afraid to have “the conversation” even though we’re in a world that’s so changed from the ‘50s. I think it’s good for people to talk about sexual dysfunction and sex in general because it’s more positive for our society if it’s not something that we’re afraid of. 

You’re also a prominent and well-regarded actress on Broadway. You’ve starred in many shows, and most recently in a Tony-nominated, show-stealing role in Kinky Boots, which is clearly a very LGBT positive show as well. What was your experience being in a show that is not only a huge Broadway hit, but also has a very powerful message to spread? 

I’m so proud to have been a part of the original company of Kinky Boots because I got to watch people change by that message, and I got to watch people see it and hear it for the first time. We knew the first time we did a reading of it that the show had a palpable heartbeat, and I feel like it hit the back of the theater every night. In some ways as an actor, I feel like if you can change somebody’s mind each night, then you’re doing your job, and I feel like we watched people walk out of that theater with a changed heart and a changed mind about equality and diversity and love. I’m so proud that I was a part of that show. And right now I’m in rehearsals for You Can’t Take It With You, which is a play that was written in the 1930s, yet the themes of it continue to be relevant today and well into the future. Similarly, it has a theme of  living for today, not for tomorrow. The title is literally, You Can’t Take It With You. That says it all!


With The Cast of Kinky Boots

I’m so excited to see that! There’s so much opening on Broadway soon and I think that’s one of the shows people are most excited for.

Right? It’s such a beautiful play. James Earl Jones is an icon and a legend and watching him play this role is like an acting class every day. Just beautiful and effortless. And Rose Byrne is making her Broadway debut, and I predict that she will be a treasure of the American theater because she’s giving such a beautiful, delightful, delicious performance. The rest of the cast is an outrageously gifted bunch of insanely credited and awarded actors who are all outrageous in their own special ways. It’s the ‘all-star character brigade,’ that’s what I keep saying. 

Now, is there any chance we’ll get to see Betty singing on Masters of Sex? Perhaps a musical episode?

Actually, it’s funny that you ask that. Not to give anything away, but in the next episode Betty does sing to Gene. We had a big conversation about this because it was helpful in the story telling that she was singing to him, but it would not make very much sense for Betty to have a great voice. Like, it just didn’t make any sense. So I do sing, but I sing as Betty would sing, which is not well. So I’m singing as Betty and singing not well, and I’m also dancing in You Can’t Take it With You and I’m dancing not well. Like I’m terrible. But it’s part of the play! When you've been raised singing and dancing, taking every class you possibly can to be the best you can, trying to sing bad and dance bad is very challenging! God, that sounds really conceited, I don't even mean it like that! But it goes against everything that you've been taught.

Well, I can vouch personally that you know how to put on an incredible solo show; I saw your cabaret "Lost in The Stars" in February at (popular NYC venue) 54 Below, and it was some of the most fun I’ve ever had there. Do you have any more of those shows planned for the future that people can catch you in?
I actually do! I’m doing "Lost in the Stars" again in December: the first three Mondays in December. So I won’t be singing on Broadway but I’ll be singing down the street. And it’ll be the holidays, so I’ll add a couple holiday jams. I feel like cabaret is kind of a lost art form - not lost, but we do it a little differently now - so I really love exploring it. It’s very thrilling and terrifying at the same time, but it’s one of my favorite things.

Masters of Sex airs on Showtime Sundays at 10 ET/PT, and you can catch Annaleigh live on Broadway in You Can’t Take It With You starting previews on August 26th at the Longacre Theater in New York. Tickets are also on sale at for her solo cabaret, Lost in the Stars. If you’re in the area, definitely don’t miss out! 

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