Actor Jae Benjamin recently shared his experiences about working on the set of the new movie, “The Legend of Jack and Diane,” a feature film that stars the late Tom Sizemore, and also sheds some insight into his 30 year push to break into Hollywood. In this film, Jae plays a pivotal role, sleaze-bag crooked attorney, ‘Monty Moskowitz,’ alongside Sizemore, who plays Detective Parker and who sadly passed away March 3, 2023, just 26 days before the film released on Amazon Prime.
In an exclusive interview with The Hollywood Times, Benjamin shares his thoughts on working onset and befriending an experienced actor like Sizemore, the challenges of Hollywood, and the importance of persevering through all odds to make your dreams come true of becoming an actor or actress in Hollywood.
Tell me about your backstory, how did you get into acting and producing?
I got into acting at a very young age after moving back to the Philadelphia area after a horrific 4 years in Marietta, Georgia in the 1980’s. Being a Jewish kid from Philadelphia wasn’t a good thing back in those days. Because I was a Jew, I wasn’t allowed to be amongst the other kids in my class in school, I wasn’t taught how to read or write or socialize. Worse, I was forced to stare at a wall all day in the corner and if I dared look away before the end of school they’d beat the s–t out of me. The neighbors, parents and their kids in the neighborhood were not kind to Jews back then either. I literally had to fight every day to stay alive. I was shot once in the leg running away from older kids with swastika on their clothing and tattoos. Those kids beat me up so many times I can’t count. All said, when we finally got back to the suburbs of Philadelphia, I had no idea how to make friends and was behind every other kid my age, educationally speaking, and in being able to mature and evolve. To say the least, I was alone a lot in those days, while all the other kids had friends and played outside. I failed most of my classes in grade school. All the reading and writing, grammar classes–but I excelled in the arts and gravitated to all things audio/visual/ creative writing, drawing, painting, sketching etc. I was able to take art classes and those types of courses in elementary school all the way through to high school. I attended what was at the time, the number one school system in America. It was pre-high school when my parents decided (along with tons of therapists/ psychologists more f–ked up than I was back then) to start sending me to overnight camp in the summers to maybe make friends and evolve as a damaged soul, that I was introduced to the stage, theater and the acting life and community— The ability to become someone I’m not was perfect for me. I’ve been hooked ever since and never looked back. Since I was 10 years old, all I’ve ever wanted to do was be an actor in Hollywood movies. I auditioned for the movie “BIG,” starring Tom Hanks. Director Penny Marshall called and had offered me the role that ultimately went to Josh Baskin. My parents said “No way are you going to Hollywood to be an actor. You’ll become something stable and go to college etc.” I was ten years old at that time.
This is why I am so grateful, I recently filmed the first picture I have a role of significance in, which is currently streaming on Amazon Prime and working on the next 3 films. For the first time in my life, after 25-30 years of hard work and dire struggles, I finally feel like I’m doing what I’ve always dreamed of and worked so hard for, acting in Hollywood movies!
You recently did a movie with Tom Sizemore called, ‘The Legend Of Jack and Diane.’
This was a fantastic experience working on the picture while onset. I play sleaze-bag obnoxious but lovable attorney “MONTY MOSKOWITZ.” I am appreciative of my dear friend Jackie Kaplan Kallen for bringing me onboard the project and giving me a chance to prove my worth as an actor in Hollywood, as well as, executive producer and co-writer Rick Geller.
What was it like working with Tom on his last film?
Sizemore was a cool guy and very kind to me. I got taken to his house the day I personally wrapped on the picture. We spoke for a while about the film we were filming, his work with Spielberg and others, some super funny stories I won’t repeat and his undying love and attention for his children— coupled with what he does as an actor. It was an honor to get to know him. He was scheduled to appear on FanRoom LIVE, the show I host and executive produce with Cedric The Entertainer for a charity event furthering his sobriety. He was doing great. He had been clean and sober for quite some time and was putting in the work everywhere he could, even teaching open classes in LA to actors and Hollywood hopefuls.
How hard was it to prepare for playing a sleazy lawyer?
Monty definitely is a slick guy but has a huge heart and soft spot which wasn’t too difficult to become a conduit for, as I’ve met all sorts of low life criminally involved and dirty attorneys and people with huge hearts but do grey stuff shall we say, all the way up to some of the most prestigious and top lawyers literally in the world.
Sadly, when you’re trying to break into the Hollywood film business, while everyone is fighting to keep you out of the Hollywood film business, and are crapping all over you, derailing you, you meet all sorts of nefarious characters. As the idiom says, “everyone from everywhere, all walks of life, meet and or cross paths at the bottom on the way up.” I use all those encounters and past life experiences to bring on the emotional skeleton and core I need in order to transform myself into the character presented on the page for me to portray.
I noticed in your social media post you said it took 30 years to get there. Can you explain?
In order to become an actor in Hollywood at the level I want, you have to make sacrifices. I’ve sacrificed my entire life to break into this business. Literally. Most people my age I know are married with children, stabilized, well off, successful in their careers, some can retire. I’m just getting started in my early 40’s. It’s not easy to break in to Hollywood. It’s not like there’s a maitre d’ at the “big break door” standing there with a huge welcoming smile, white gloves to open a velvet rope to let you into the club you’ve worked your ass off to become a member of. No way. It’s a battle, everywhere from everyone you can imagine and can’t imagine but I assure you one thing, IT’S WORTH IT! I wouldn’t change a thing! All the years of learning, growing, crying, and often more painful moments than great ones— the blood sweat and tears–all worth it. More lows than highs, it’s all worth it to take your dreams and make them reality. Truly! I embrace it all. Had I known what I know now, I’d probably have broken in years ago, but those who set out on this path all cross the finish line at different moments in life. I was always a slow learner. It took me a long time to figure it out the meaning of life.
“What’s meant to be, is meant to be and will be, when it’s meant to be.” That simple and that hard.
Any new projects coming up you can tell us about?
Yes! 3 new pictures so far I film this year. Two are studio pictures. All I can say is I’m beyond elated and just feel so lucky, blessed and grateful. I have an uncontrollable feeling of gratitude and lucky to be able to do what I love and have dreamed of doing my entire life, being an actor in Hollywood movies. Yes I’ve worked my entire life and given my entire life, sacrificed everything you could imagine to get here to this very moment, but, some ‘lucky-meant-to-be’ life changing moments happened which made all that’s happening now happen. Law of attraction in action, at its best. The universe has been aligning everything I’ve been wanting and asking for and lining it all up in perfect timing and chronology. I finally see that and get it now. It’s taking me my entire life. This awareness is awesome and now rewarding and changing my life for the better and allowing me to finally do what I love and have worked so very hard for and dreamed of since I was a young child.
