Pillow Talking’s Interview with Actress, Singer, Musician, Producer CASSIDY FREEMAN

Someday Productions LLC and Pillow Talking are pleased to present the following interview with actress, singer, musician, producer Cassidy Freeman



Pillow Talking had the pleasure of interviewing actress Cassidy Freeman by telephone shortly before the holidays. In anticipation of any problems we might have had on either side, we all laughingly gave our apologies for any potentially unwelcome canine interruptions. We at Pillow Talking have three dogs, two yippy Pomeranians named Cody Elvis and Lucky Jackson and a rather boisterous Golden Doodle puppy named Killian Jones; Cassidy has a Swiss Mountain dog named Shasta. (FYI: Intermittent barks were heard throughout!)

After the introductory hellos, we briefly discussed the fact that in addition to acting, we’d read many things about Cassidy, including that she is in a band with her brother, The Real D’Coy, in addition to what some of her hobbies are. Cassidy told us that she gets quite a kick out of the things she reads. “Our ‘cyber selves’ are so funny,” she said. “I quilt. But why is that on the Internet? I do a lot of things!” We all had a chuckle.

Chicago native Cassidy is a multi-hyphenate, actress, producer, singer, and musician with an impressive resume and strong connections to family – all of whom share a love of the entertainment business. She has worked on multiple projects with her brother Clark and her oldest brother Crispin has a lengthy list of credits as a voice-over artist. Maybe best known for her role as Lex Luthor’s protégée Tess Mercer in Smallville and Cady Longmire in Longmire, she also had a memorable role in season three of The Vampire Diaries as Sage.

This talented, determined and hard-working artist took time out of her busy schedule to speak with us. We have the great pleasure and honor of bringing this insightful conversation to you!

PT: So we know you have brothers, some of whom are in the entertainment business. Tell us about them.


Clark Freeman


Crispin Freeman

CF: I have three brothers – two biological and one adopted. Here’s a funny story – my oldest brother, Crispin, [when he was a kid] had interviewed my mom for a project and he recently found the tape, so he digitized it and gave it to us for Christmas. Mom has since passed. It was amazing – three or four times you can hear me saying, “Mommy, my nose is stuffy” and he got so frustrated!

So being the only girl in a family of four kids (and being the youngest) makes for an interesting situation. I was born in downtown Chicago. My parents were both corporate litigators. I was partly raised by a woman – a nanny who was more like a second mom to me. This enabled my mom to go back to work – she was a pretty hard-core mom. She and my dad eventually worked together.

I got into dance early. My mom lied about my age – she said I was five when I was three. She got me into ballet. Thank God I was a tall child! She was an oil brat, grew up in Texas. She was the eldest of four and the only girl. She grew up dancing. I was on pointe by the time I was eight years old. I love, love, loved it. I loved to be on stage, performing. At 14 my mom pulled me aside to talk to me about my future in ballet. She said I could go for it or not – I was talented but I was too big, too athletic. She was only partly right.

It’s funny – there are dancers I’ve seen in Aspen Santa Fe who are beautiful, strong, athletic dancers – it’s mind-blowing.

PT: So you’d had this strong background and developed a love for performing.

CF: Yes. I loved being on stage. And I had these two brothers who were actors in school. I looked up to them. I loved performing and telling stories. And I was in the Lyric Opera of Chicago where they allowed little kids in opera.

I believe that you do what brings you unconditional joy. On stage you lose all those inconsequential social things. It feeds your heart – and it doesn’t matter who’s watching. In the world of acting there are so many different ways of expressing yourself. So many different ways of telling stories. So many different kinds of actors. Acting is where I find a lot of joy and it comes to me the easiest although it is not easy for me. But I would always choose it over other things. If it was Broadway or the band – I’d have to say to my brother, I love you, but…

PT: (laughs) Tell us more about your brothers.

CF: Clark, my middle, biological brother, and I were like twins born five years apart. We’ve always been very close – it was almost like we spoke a different language. Together we co-produced a horror film, developed a TV series – partly about my father’s life. And, of course we play in the band together.

It keeps our relationship really current and present. People tend to keep relationships as they were and they stay in that. This lets each other change. I’m so happy to work with him; it keeps our friendship authentic.

All of us (biological children) are actors. It keeps the closeness between us. I idolized them so much; I grew up really quickly. The age difference didn’t matter. Behavior is modeled for us – our parents lived together and ran a business together.

It’s funny though (with Clark) we’ve worn T-shirts “He’s my brother” and “She’s my sister” – people mistake us for a couple. We are into the same kinds of stuff – so we just figured, why not do it together. It’s nice to have the same language.

And Ryan, the nephew of the woman who raised me – he was my brother, despite being Ida’s nephew.

PT: Tell us about the band you have with your brother — The Real D’Coy.

CF21The band started as my brother Clark, who is the drummer, and his friend Andy Mitton on guitar. They asked me to show up one time – then Andy and I started geeking out on these fun harmonies, both doing a cappella. I play the keyboard. The bassist, Kurtis, is a phenomenal musician. We were invited to the Isle of Wight in England which was incredible. We recorded our second album in 2014 in Santa Fe. It’s always been my brother’s dream – to drive around in a Winnebago, eating granola bars and McDonald’s, performing in bars. But Andy moved to Connecticut. We’re still making music together – I think if we got together every couple of years and recorded an album, I’d be happy.

PT: Who or what were your early influences (in acting, singing, or artistically)?

CF: My brothers definitely were my hugest influences, getting to watch them. My parents only watched Turner Classic Movies – the best comedy, dancing, singing; all black-and-white movies. We were not influenced by pop culture as much as other kids. It felt like higher art to me. So did listening to and being in opera – I never loved opera, but I loved singing.

And I love Laura Linney. I watched her perform in Sight Unseen. She was just phenomenal onstage. There are a lot of pretty people in this world – and I’m the first to admire them. There is just this energy when people are onstage. And it doesn’t really matter what they look like, but they shine. Laura Linney is like that for me.

My mother used to sing and play piano. I grew up in a house with a lot of artists and performers.

PT: What was it like for you growing up?

CF: Our only real family time was on our ranch in Montana. In Chicago there was no telling who was going to be home for dinner. We were really busy from very young ages – city living provides you with a lot of opportunities and our parents worked hard in the business.

In Montana, family time was off a 14-mile dirt road. We didn’t have TV, we were lucky to have electricity. We made music, played games. It was great.

PT: How did your professional career begin?


Cassidy Freeman as Tess in Smallville

CF: I did movies and shorts here and there. But one sparked it all – I was cast in a show at the Atlantic 2 Theatre in New York City. It was a radio play called Cigarettes and Chocolate. Then I went to L.A. for three years before going back to New York.

I had booked a pilot called Austin Golden Hour that didn’t get picked up. I didn’t know what I was doing. Then I got Smallville. I did 22 episodes – it was three years of my life. It was like being in grad school, a lot of work, I was on my own, I’d moved to Vancouver. And I missed my brothers.

But I didn’t feel like I’d “made it” at that point – although professionally I felt I had come through some kind of first wave. I was taken seriously. But I had to work to maneuver my career.

PT: Do you prescribe to any particular acting “technique”?

CF: I think I don’t really have a technique – like you can’t sign up for a team and then just succeed. You really never stop learning. Acting is kind of like a muscle – like going to the gym. The emotional gym. But ultimately you have to decide what works best for you.

From a young age I was strictly trained how to behave – as a kid in the Lyric Opera, you didn’t get out of line. You listened, did what you were told. You showed up on time, respected the space. You followed the rules – you did no wrong.

You have to be the artist you want to be in the space. When I was in college I had this professor – he would have us pick a card. Each card was a new way to learn to explore. We learned to tap into real emotion on stage.

PT: So you had a great foundation.

CF: Well, I felt that I was very well trained when I came to L.A. I was like, I can do anything you want me to do on stage. I could do emotions, be angry, do stage fighting. Then I went into Playhouse West where they study the Meisner technique. I had this long list of reasons why I was so right for it, so professional. That was until Rob Carnegie said, “Okay. Now throw that out the window.” So I said, “Absolutely Sir, I can do anything you want me to do.” (laughs) He made me the instrument that I am.

Those three years taught me my emotional self. It gave me a depth to my work I wouldn’t have found on my own. I am grateful for all of it.

Now I do what feels right. There is a super vulnerable place actors have to go. You need to have faith in yourself. You need to have knowledge. You need to throw it all out there. You are going to be seen and judged by other people.

PT: (Stephanie) This is going to be a purely selfishly motivated question, but my daughters love The Vampire Diaries. Tell us about that experience.


Cassidy Freeman in The Vampire Diaries

CF: It was super fun! I had met the showrunner, producer. I had shot a pilot in Vancouver, was working on Smallville (it’s a small world, this business). I was recommended for the part – I was told it would be really great for me, and I was like, “Absofreakinlutely!”

It was the most badass character ever. This 400-year-old teacher of [the character] Damon, who taught him to be the ruthless vampire he becomes. They tell me, “And you’re a boxer in 1912!” I don’t know how you can get any cooler!

I spent six weeks in Atlanta, Georgia. It was really fun. It was my first role that was an “offer” – it is lovely to be invited, really.

PT: (Stephanie) Now can you tell us about Once Upon a Time? That’s a favorite of mine and one I watch with my girls.


Cassidy as Jack in Once Upon a Time

CF: I thought the premise for the show was super clever! I had a really fun time working on it. Jack [and the Beanstalk] as a female was really cool. I got to meet Jorge Garcia – who I watched on Lost, and I’d admired his work. And Josh [Dallas] was lovely to work with.

That was a fun one. A different experience. It was shot in Vancouver – and it was a fantasy world.

And the costumes! All the costumes were made for me in two days – they were incredible! They handed me this seven-layer, hand-made leather thing. I was like, “Is this for me? And can I take it home?” (laughs)

PT: (Stephanie) Wow! I know those costumes are amazing. I always admire them! Now can you tell us about Longmire?

CF25CF: Sure! I’m one of the regulars on the show. I’m the lead’s daughter. We’re going into season five in March. It is a really cool show, based on the mystery novels of the same name.


Cassidy in Longmire

We were with A&E for three years but they dropped us – we had 6 million viewers (5 million were over age 60) but not enough pull for commercials – you have to sell ad space, you know. The showrunners at Netflix loved it and picked it up as original content. The last season – Season 4, was the most watched. Netflix doesn’t share their [viewer] numbers. It’s great – the episodes are longer and we don’t have to write for commercial breaks; the episodes feel like little movies. It’s really cool.

And lately I’m recognized more often in public – I know more people are watching!

PT: Tell us about your other endeavors, like producing Cortez.


On the set of Cortez

CF: It’s a dream job! I didn’t expect to enjoy producing as much as I did on Cortez. Producing is like the Eskimo word for snow – there are 27 different definitions. Take the word producer – it means creator, maker. I will take all ideas through to the finish. I love making shit!

And I love being chosen. At some point in the last five years I decided I was sick of waiting to be chosen. I would rationalize, It wasn’t right for me at the time


Cheryl Nichols on the set of Cortez

I decided the only time I was going to be chosen is if I make it myself. Technically it’s like wiping out that hierarchy. I think there are a lot more opportunities out there – and it takes a village.

Basically I was helping friends in reading a project – and I was like, “How can I help?” (laughs) They looked at me sideways and said, “Do you want to produce it?” I was never that driven to get behind the wheel. But I love being part of a team. I love helping people find their strengths, seeing the shine in them.

We are doing it without the help of a studio, but we’d love for a studio to buy the project.

PT: This wasn’t the first time you were a producer, right?

220px-YellowBrickRoad_movie_poster_2010CF: I was a producer on Yellow Brick Road. I was doing Smallville then so there was no pre-production. My brother Clark played my brother in the movie – his part was larger than mine. We did the movie in New Hampshire and had a really great time – we included people from Middlebury where I went to college. We used current students and faculty as production assistants and in the cast.

PT: What is the hardest part about being a producer?

CF: Raising money! It matters how you get it and who you get it from…No matter what, you have to believe in the project – but it takes money to do it right. I’d rather pay crew than special effects. You want people to feel taken care of – that they are treated well.

And as a “creator” you have a vision in your head. But as you go down that road, you have to compromise and sacrifice that vision. It’s never going to be as you first saw it in your head. Then it’s how you live with the compromise. Perception creates reality – you can have this innate sense that things went wrong, but instead of living in fear of that, you can allow the project to take its own journey – to have its own life. If things didn’t happen the way you envisioned, it wasn’t supposed to be. Producing has been a place for me to learn. The project often becomes better than it was supposed to be.

The editing part is tough – watching things fall away – like I’m killing all my dailies, all my moments.

PT: So you really become invested!

CF: Projects become like this living, breathing thing. They change. They go in different directions. It’s like it gets a haircut – shaped, molded, punched, lifted, thrown. It’s like the most layered cake you’ve ever baked in your life.

I’ve learned to accept it and just not look at any of it as compromise. I’ll say, “How do I work through this thing on this day?” And when I feel overwhelmed, I know I can only slay one dragon at a time.

For me, producing is like summer camp – acting is the school year.

PT: What is the status of Cortez now?


Cheryl Nichols on the set of Cortez

CF: (laughs) We are in post-production Hell. The group is incredible though – Cheryl Nichols – she’s the director, star, co-writer, co-producer, co-editor. She is a real renaissance woman. We met eight or ten years ago. We’d both just landed in L.A. and she’d beat me out for the lead in a student film. I never let her forget it!

It was tough to meet other women in this town – I didn’t engage in that shit. I would turn and walk the other way. But she was like, “You’re my people.” So I stayed and we are now great friends. She is gorgeous, a great actress, and phenomenal to work with. Our careers have gone on different trajectories – when she struggled to make headway, I continued to work. It didn’t feel fair, but maybe it was meant to be that she wasn’t acting in her 20s – she struggled through it to achieve true greatness. She added so many more tools to the toolbox.

I wanted to help and support her. I thought I could help her create this for it to become her calling card. At one point she freaked out – the director had bowed out. I knew it already – but then Cheryl realized she was supposed to direct. She called me and said, “I have this crazy idea. What if I direct?” And I was like, “Finally!” It all lined up. I’m so happy for her – things are just beginning for her in terms of her directing and writing abilities. We’ll be submitting it to festivals – fingers crossed!

PT: Tell us, what do you think about these new TV and film platforms? Netflix obviously worked for Longmire. How do you think they are on the business as a whole?

CF: I think it’s a train no one can stop even if they wanted to. Just go limp – it hurts less! It is the future.

I tend to be a nostalgic person, but I love the new platforms – it promotes freedom in creating, freedom in watching. Everyone has the freedom to do what they want. I don’t know the others as well as Netflix, but they are the smartest company. I love that they don’t share numbers. They are responsible for the programming. It is a leveling ground. I am eager to see what happens.

It’s not old Hollywood anymore. There’s less [money] for every person involved.

PT: How do you balance everything?

CF: Coffee is one answer!

PT: (Stephanie) I know all about that!

CF10CF: (laughs) Yoga is another answer. Know your church I always say. And you can throw a ball to your dog!

My mother always said if my candle had three ends, I’d burn all three. I am very involved in a lot of things. I used to think it meant I couldn’t be great at anything, but I don’t think that way anymore.

I am grateful for what I have – but I know when I’m pushing too hard.

And sleep is important. (laughs) If I could tell young me anything, it would be, “Sleep more – you’ll be more productive.”

I was involved in so many things when I was young – I was not a great student. I didn’t test well. I could have a conversation about things, but I was not great in a scholastic way. But you have to be here, present, willing, even if you’re not good at something. If you want something and have a willingness to put yourself out there, that speaks volumes. And each thing informs the next.

When there is joy in what I’m doing – as I keep doing – I have more energy and I get more excited. It is a great internal barometer – it’s a great way to check in with yourself. But you also have to have the maturity to know to let things go when they don’t serve you.

PT: Is there anything on your bucket list?

CF: I want to spend time in Asia. I want to go to Bali, to India. I traveled a lot as a kid – but then [you grow up and] work happens.

I’d also love to do yoga teacher training – to get deep into that side of me. It sort of scares me, it’s unfamiliar. I want it to be familiar.

I also have a dream to play a certain old movie star – but I don’t want to say whom. And the more I work on my TV show with my brother, the more I want that, too. I also want to be on Broadway. I don’t know how, or when I will be. But I will be.

No matter what, I try not to think so far into the future.

cassidy-freeman-300120113130632PT: If you could sum up yourself in one word, what would it be?

CF: Freedom. Free – it’s in my name. It’s a great reminder for me.

Cheryl told me, “You only live once, dummy.” You only live this life once. All beings are supposed to be happy and free. We tend to take things for granted and we don’t let ourselves feel. I want to lead by example. I want to be free.

PT: Thank you so much, Cassidy, for an amazing and very enlightening interview!!



Stephanie & Wayne

About Stephanie & Wayne

Stephanie is a journalist, writer, editor, and has had several hundred articles published in various newspapers and magazines, many of which still are available online under “Stephanie Lyons Schultz”. She has a Masters degree in Counseling Psychology and was a practicing psychotherapist. She currently is a professor of psychology at WCSU and NVCC in Connecticut. Wayne is an Emmy-Award winning writer, producer, and director. He has produced many programs and documentaries that have appeared on television, and have been distributed to schools, libraries, and home video. Wayne also is a practicing attorney with a Masters degree in Law from NYU. In addition, he is a professor of communications at WCSU. Together, this recently wed couple write, produce, and direct as many of their stage, screen, and TV projects as they can with a full house -- their combined brood of seven! Some of their work has been featured this summer and fall off off Broadway; other work currently is under option. They hope to continue to promote more of their projects in the coming months! Feel free to write whatever comments you like! We want your feedback!