The world of drag and pageantry is often synonymous with glamour, sequins, and dazzling performances, but behind the glitz lies a journey of resilience, self-discovery, and an unyielding spirit. In this special interview, we have the privilege of speaking with the remarkable Jerrine "Jerrine Jeffries" Kaiulani Madayag, a legendary showgirl and an influential figure in Hawai’i's LGBTQ+ community. Her story is one of survival, transformation, and triumph. From her early childhood in foster care to navigating a complex family dynamic, Jerrine's life has been a testament to perseverance. Born on May 1, 1953, in Wahiawa, Oʻahu, she faced adversity from an early age. Raised by loving foster parents until the age of seven, she was later introduced to her biological father and an unfamiliar household where she encountered hardship and abuse.
Yet, through it all, she remained steadfast in her identity, even as she faced ridicule for being "mahu" (a term used in Hawaiʻi for gender nonconforming individuals). Jerrine's teenage years were marked by struggles with schooling, identity, and finding a sense of belonging. By the age of 17, she had discovered a world that would change her life forever, the vibrant, captivating world of showgirls. Her first visit to the Glade Cocktail Show Lounge was an awakening, igniting a dream that would eventually become her reality. However, the journey to self-realization was not without challenges. From navigating military life as an openly feminine individual to facing personal battles with self-worth and acceptance, Jerrine's resilience shone through. By her mid-twenties, Jerrine was embracing her true self. Her journey took her from military service to the heart of Hawaiʻi's drag scene, where she found her calling as an entertainer. In 1989, she won her first pageant, marking the beginning of a successful career as a performer.
Over the years, she graced countless stages, won prestigious titles, and became an integral part of Hawaiʻi’s Imperial Court System, where she dedicated herself to community service and mentorship. Jerrine's contributions extend far beyond the stage. As a leader within the LGBTQ+ community, she has used her platform to uplift and support younger generations, ensuring that the legacy of love, acceptance, and advocacy continues. From being crowned Queen of Queens at the Hawaiʻi Boa Arts Ball to serving as an Empress in the Imperial Court of Hawaiʻi, Jerrine's impact is immeasurable. In this interview, Jerrine shares her incredible journey, offering insights into the challenges, victories, and defining moments that shaped her into the icon she is today. Join us as we celebrate the life and legacy of Jerrine Jeffries, a trailblazer, a mentor, and a true queen of queens.
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| Empress 26/29 of The Imperial Court of Hawaii. |
Monika: Today, I have the pleasure and honor of interviewing Jerrine Ka’iulani Madayag Calantoc, also known as Jerrine Jeffries, an American entertainer and beauty pageant queen. She is the Former Empress 26/29 of The Imperial Court of Hawaii, Former Golden Goddess '97, and Queen of Queens 2000 of The Hawaii Boa Arts Ball Pageant. She was also the 2nd Runner-up at the Universal Showqueen Pageant Hawaii in both 2006 and 2007, as well as the 4th Runner-up at the Continental Elite Beauty Pageant in Chicago 2006. Currently, she holds the title of Miss Fusion Waikiki Honolulu. Additionally, Jerrine is a former cast member of The Paperdoll Revue and The Glades Revue. Jerrine, welcome! It's an absolute delight to have you here today.
Jerrine: Aloha, Monika! Thank you so much for having me, it's an honor to be part of this conversation.
Monika: You look absolutely fantastic, Jerrine. What are the secrets behind your timeless beauty, and how do you maintain such a radiant appearance?
Jerrine: My Asian bloodline and my doctors. It also helps to have a positive mindset and embrace who you are. Keeping a healthy lifestyle with regular exercise and good nutrition is important too.
Monika: Could you share a little about your journey and how you got to where you are today?
Jerrine: Well, as you know, I’m from the beautiful islands of Hawaii. Born May 1, 1953, I am 61 years of age, Hawaiian, Filipino, Chinese, German, Irish, Indian, Spanish, and most importantly, I'm a Transsexual. I transitioned at a late age of 27 and set goals for myself and accomplished 90% of them within the past 20-something years. At first, it was hard, as we all know. Growing up, I had a difficult childhood. I was raised in a loving foster home after being born under complicated circumstances.
My birth parents were not married, and I spent my early years with Antone and Flora Souza, who were very nurturing. Later in life, I changed my name to Jerrine Kaiulani Madayag in 1987 and continued to face the challenges of being a transgender woman in a world that was still not fully accepting. But overcoming adversity became my strength. I finally had my gender confirmation surgery in 2018, and I’ve continued advocating for trans rights and visibility, which are so important to me.
Monika: What inspired you to pursue a career as a stage artist, and when did you first take the stage?
Jerrine: My first appearance was back in the 70s at the Glades Show Lounge in Honolulu. It was a defining moment for me, and I knew that performance was where I belonged. The energy and excitement of being on stage made me feel alive, and I quickly became captivated by the art of performance. Over the years, I found that being able to express myself through music and dance became a powerful way to connect with others.
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| Miss Fusion Waikiki 2014. |
Monika: Could you share some of the venues and shows you've had the pleasure of performing in?
Jerrine: I’ve performed at venues like Fusion Waikiki and Venus Night Club. In addition to these, I had the privilege of being a part of The Paperdoll Revue and The Glades Revue. Those performances were so special to me because they allowed me to showcase my talents and connect with the vibrant local community. These stages were where I really grew as an artist and honed my craft over the years.
Monika: Have you ever considered pursuing acting?
Jerrine: Not really, acting never crossed my mind as a career. However, I have always enjoyed being on stage and performing, especially in shows and revues where I could express myself through dance and music. It’s more about the live energy and connecting with the audience for me than diving into acting itself. While acting wasn’t my focus, performing in front of people has always been a fulfilling experience.
Monika: Can you tell me about your first beauty pageant experience?
Jerrine: Yes, I competed in the 1993 Miss Elsies Club Polynesian pageant, and I won! It was such an exciting moment for me, marking the beginning of my journey in pageants. The competition was tough, but I was determined and had a strong sense of self-confidence. Winning that title was a huge step forward, and it motivated me to continue striving for more in the pageant world. It also helped me build my presence in the entertainment industry.
Monika: Could you tell me more about some of the most memorable pageants you've participated in and the trophies you’ve earned?
Jerrine: One of the most exciting competitions was Hawaii's Universal Showqueen Pageant. It’s a Las Vegas-style event with categories like Black and White Couture Cocktail, Evening Gown, Talent, and Showgirl Costume. But the title I’m most proud of is becoming Empress of the Imperial Court of Hawaii. That experience allowed me to give back to the community, raising funds and donating to organizations like Life Foundation, The Gregory House, and Save the Food Basket.
Monika: Beauty is often a source of empowerment. Do you find that your beauty gives you strength, and do you use it to your advantage?
Jerrine: Well, I’m naturally a very modest person, but at times, I do find that my presence can be empowering. It’s not just about how I look, though; it’s about how I carry myself. My experiences in pageants and performances have given me a sense of confidence, and it helps me inspire others. In those moments, I do use my platform to uplift those around me.
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| Performing with The Paperdoll Revue on 7/16/2014. |
Jerrine: In the early stages of my transition, I was mostly alone and navigating things on my own. But as time passed, I found my true calling in entertainment, and that's when I discovered some incredible role models. One of my biggest inspirations was Miss Yoshiko Oshiro, who became a guiding light for me. She showed me the strength and grace I needed to thrive in my career. Her impact on my life and my transition was profound, and I always admired her for paving the way for others.
Monika: What was the hardest part of your coming out journey?
Jerrine: Honestly, the hardest part was finding the strength to be myself in a world that wasn't always accepting. However, I was fortunate to have an amazing support group — my family and friends were always there for me. They gave me the confidence I needed to take that step. Over time, I learned to embrace my identity and even found a community of like-minded individuals. The love and acceptance I received helped me push through the tough times, making it all worth it.
Monika: How do you feel about the current situation of transgender women in American society?
Jerrine: As a child of the 50s, we transgender women have experienced and overcome many challenges. But, I must admit, we have truly made an impact on society in more ways than one. We are active in so many aspects of life now, breaking barriers and opening doors. While there’s still work to be done, we are here to stay, and our voices are being heard. The journey has been difficult, but it's inspiring to see how much progress we've made together.
Monika: Many transgender women face the difficult challenge of wondering whether they “pass” as women. You are a beautiful lady yourself, but what advice would you give to those who fear they may not pass?
Jerrine: As Yolanda Adams sings, "Never Give Up," stay strong and true to yourself. It's important to remember that passing is not the only thing that defines your worth. Confidence and authenticity radiate more than anything else. Embrace your journey, and know that beauty comes in many forms. Surround yourself with supportive people who lift you up, and remember that you are already enough just as you are.
Monika: Do you think transgender rights could become the new frontier for human rights, pushing society to evolve in new ways?
Jerrine: Of course! Transgender rights are an essential part of the larger fight for equality and justice. As we continue to push boundaries, we’re paving the way for future generations to have a voice in society. The recognition and acceptance of transgender people is not just about us, it’s about a more inclusive and compassionate world. The journey is long, but the progress we’ve made already shows the potential for change.
Monika: Are you involved in politics, or do you participate in any lobbying campaigns? Do you believe transgender women can make a real difference in politics?
Jerrine: Somewhat, and yes. We do have a few transgender women in office, like Kim Coco Iwamoto on the Hawaii Board of Education, and Kumu Hina Wong vying for the seat of the Office of Hawaiian Affairs. I believe transgender women have an important voice in politics and can drive meaningful change. As more transgender individuals gain political representation, we can bring fresh perspectives that challenge traditional policies and push for inclusion across all sectors of society. Representation in politics is essential for advocating for our rights.
Monika: How important is love in your life, and how has it influenced your journey?
Jerrine: Love from family and friends is the most important to me because, without their support and love, it would be very hard to go on and pursue whatever I wanted. They have been my backbone, and their encouragement has always kept me moving forward. Love gives me strength, especially in difficult times. It’s the foundation that helps me overcome challenges and keep pursuing my passions. I truly believe that love, in all its forms, is the key to personal success and happiness.
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| Last month performance with The Paperdoll Revue. |
Monika: How would you describe your relationship with fashion? Do you have a favorite style or designer? What kinds of outfits make you feel the most confident?
Jerrine: I am such a fashionista that I’ve turned my spare bedroom into a walk-in closet! I love anything that looks good on me and makes me feel confident. Chanel and Emilio Pucci are among my favorite designers, but because of my body size, I can easily walk into clothing stores and buy straight off the rack. I gravitate toward bold colors and elegant styles that showcase my personality and create a strong presence. Fashion gives me a sense of empowerment, and I enjoy experimenting with different looks.
Monika: Have you ever considered writing your memoir? What aspects of your journey would you want to share with others?
Jerrine: One day, I would love to write my memoir, but I’m not quite sure where to start. I think there’s a lot to share from my journey, what it’s like growing up in Hawaii, my transition, and the lessons I’ve learned along the way. It could help others who are on a similar path. I believe it’s important for transgender women to tell their stories, as it brings visibility and can inspire those who feel alone. It’s a way to show that we are resilient, strong, and worthy of being heard.
Monika: Looking ahead, what is your next step in life, and where do you envision yourself in the next 5-7 years?
Jerrine: You know, I’ve accomplished so much in a relatively short time, and I’m very content with where I am now. Being able to mentor my transgender sisters here in Hawaii has been so rewarding, and I’m grateful for the opportunity to reach out to others both on the mainland and abroad. In the next few years, I hope to continue uplifting and empowering my community, helping more transgender individuals realize their potential. There’s always more to do, but the journey itself has been incredibly fulfilling.
Monika: What advice would you give to transgender women who are considering a career in entertainment?
Jerrine: Do it, and do it to the best of your ability. Never let anyone tell you otherwise. You are your toughest critic, so always strive to entertain and perform at your best. The entertainment world can be challenging, but your passion and perseverance will shine through. Stay true to yourself, keep learning, and never give up. The opportunities are there if you’re ready to work for them.
Monika: Jerrine, thank you for the interview.
All the photos: courtesy of Jerrine Jeffries.
© 2014 - Monika Kowalska
