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

Annaleigh Ashford chats exclusively with Shewired about playing Betty DiMello on Masters of Sex, changing lives in Kinky Boots, and returning to Broadway this month.

By: Rebekah Allen
August 08 2014 8:24 AM

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.

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