Oliver James Gregory discovered his passion for acting as soon as he was walking and talking and has not looked back since. A natural performer, Oliver thrives when expressing himself through character and storytelling, finding true confidence and joy on stage and screen. From the moment he began acting it became clear that performing was where he felt most at home, using his imagination, focus and emotional awareness to bring roles to life.
Through the expert guidance and support of NYLA Talent, Oliver has had the privilege of training with and learning from some of the industry’s finest professionals. His acting development has been shaped by working with respected actors Connor Weil and Robert Vito, as well as renowned casting director Craig Campobasso. These experiences have helped shape his discipline and growing versatility that continues to set him apart as a young actor.
Acting is where Oliver’s creativity truly shines, allowing him to express himself with confidence and authenticity. With a genuine love for the craft and a strong foundation of professional training, he remains committed to growing as a performer. Oliver continues to embrace every opportunity to develop his skills, challenge himself and pursue his passion for acting with dedication and excitement for the journey ahead.
HELLO OLIVER JAMES GREGORY, WELCOME TO ABOUT INSIDER! WHAT GOT YOU INTO ENTERTAINMENT THAT MADE YOU REALIZE THAT IT WAS YOUR CHOSEN PATH?
I’ve always loved performing and it’s been a dream of mine since I was tiny to be on the stage and screen. From a very young age I discovered that I loved stepping into different characters, telling stories and expressing myself through imagination and performing. Acting coaching gave me a sense of confidence that I loved and the more I trained and performed, the more I knew this was a path I wanted to follow. Acting lessons allowed me to challenge myself personally. I love the process of rehearsing, taking direction and working with others to bring a story to life.
WHAT KIND OF TRAINING HAVE YOU RECEIVED SO FAR AHEAD OF IPOP!?
I’ve worked really hard with acting coaches Connor Weil and Robert Vito to enhance and improve the acting skills I have. Their knowledge and guidance have been invaluable to me. Prior to joining NYLA, I trained with Beyond Broadway which was an amazing experience and also gave me an introduction to musical theatre. I became a member of the Young Artist Academy before flying to LA. The team there have been so supportive in passing on their knowledge.
WHAT ARE SOME OF YOUR FAVORITE ROLES / CHARACTERS YOU’VE BEEN INVOLVED IN?
I played Mungojerrie in Cats , which was incredible. I love exploring different characters and personalities. I’ve just finished rehearsing as Prince Charming Rockafella in Cinderella Rockafella which was great at school. I filmed my first short film under director Chandler Dunman. Mungojerrie was especially fun because of the mischievous energy and playfulness of the character. It challenged me due to the physicality involved through the dance routines and movements expressed constantly on stage.
WHAT ACCENTS AND DIALECTS CAN YOU DO?
I speak English and can add strong Scottish dialects due to living in the Highlands of Scotland.
HOW WOULD YOU DESCRIBE THE PROJECTS THAT YOU TYPICALLY PREFER?
I love performing full stop. Working on Stage is incredible because you are in front of a live audience and get that immediate connection and reaction. Having now filmed my first short film my heart is on the screen due to my aspirations to be in TV and film. Experiencing direction and team work onset was an amazing process to be involved in.
HAS THERE BEEN ONE PARTICULAR MOMENT IN YOUR LIFE SO FAR THAT YOU’RE MOST PROUD OF?
Being selected to attend iPOP in Los Angeles was a standout moment for me. It was a huge milestone and for me it confirmed that all of the hard work , training and commitment I had been putting in was paying off. The opportunity at iPOP has given me the chance to be represented on an international platform and gain more knowledge of the industry I want to be a part of. Another moment is now filming my first movie. Working on a live film set for the first time was so exciting and rewarding. I’ve always aspired to be in a movie, so this experience has made me more determined to continue pursuing acting. Being a cast member taught me so much about the work of the producers and directors and had made my passion for TV and film even stronger.
WHO ARE SOME CELEBRITY INFLUENCES THAT YOU ASPIRE TO?
There is so much talent out there, but I love Jim Carey’s fearless approach to comedy especially his exaggerated facial expressions. I love the versatility of Johnny Depp and Mark Walhberg as actors. I’m also drawn to comedy work of Karan Brar and Cameron Boyce in Hey Jessie. They are hilarious to watch.
IF YOU HAD ONE MESSAGE TO GIVE TO YOURSELF, WHAT WOULD IT BE?
I’m a Christian and believe that God puts you exactly where you are meant to be I also say just always be you because everyone else is taken. I’m young but already see the importance of being unique. Forrest Whittaker said he loved acting because of the connections, and I couldn’t agree more. The connections you make are so powerful, as you are surrounded by people who all have something special to offer. Kirsten Poulin reaffirmed this recently at iPOP and the connections are definitely a huge takeaway for me.
WHAT IS ONE WORD TO DESCRIBE YOURSELF?
Creative
WHAT IS ONE FOOD YOU WILL NEVER EAT?
Baked Potatoes – but I honestly don’t know why!
DO YOU PLAY ANY SPORTS OR INSTRUMENTS, IF SO, WHICH IS YOUR FAVORITE?
My favourite sport is golf because I enjoy the focus and patience required. I also started playing the chanter….being from Scotland it would be weird not to play the bagpipes!!
WHAT WOULD YOUR DREAM JOB BE ON TV?
My dream job on TV…. I would say a funny comedy show where I get to make the audience laugh. I’d love to play a funny/goofy character, maybe a bit silly or geeky but who is kind and loveable! The best bit about acting is you can explore different characteristics and have fun developing the personality and character.
WHAT IS YOUR THING TO DO WITH YOUR FRIENDS?
Just spending time with my friends, whether it’s video games or on the golf course, is always great fun. I have a great group of friends, and we are always laughing and having fun.
HAVE YOU SET ANY 2026 PROFESSIONAL GOALS TO ACHIEVE?
My ultimate dream would be to play the lead character in a comedy movie. I feel like 2026 is going to be a crazy but positive year as I continue to develop my acting skills with my coaches and attend auditions.
WHAT ARE YOU MOST EXCITED ABOUT FOR AT IPOP!?
The opportunities that Kirsten, German, Courtney and Shelby Lynne during iPOP! have
provided can’t be topped, can it?! Being offered a platform to network with like-minded people from all over the world has been incredible. So much talent in one place creates the best atmosphere. The connections made at iPOP! will last a lifetime for sure and I’m so happy to be educated about the industry. I’m a positive and inquisitive person by nature so I’m excited to soak up as much as I can.
ARE YOU ACTIVE ON SOCIAL MEDIA?
Yes! I am on Instagram @oliverjamesgregory
