We had the good fortune of connecting with Jillie Reil and we’ve shared our conversation below.
Hi Jillie, we’d love to hear about how you approach risk and risk-taking
I have always loved the saying “You can’t win if you don’t play.” As an artist or creative, you MUST put yourself out there. I have so many people that come to me saying “I’ve always want to try stand-up comedy” followed by a list of excuses. I always encourage those people to go NOW and hit up a mic wherever they may be. What do you have to lose? I have taken so many risks in my life, but after my divorce in rural Minnesota was a pivotal moment. I gave up every belief engrained into me as a child…organized religion, marriage, 2.5 kids, the white picket fence, climbing the corporate ladder and going to law school. I left everything behind and moved to San Diego for something new. Another chapter. A new adventure. I thought I was too old to be an actual entertainer in my early thirties, so I pursued being a makeup artist, but because I put myself out there in the entertainment world, my dreams found me for what I really wanted…comedy. My second makeup artist job lead to me being being on the runway instead of doing makeup (I had modeled in my late teens). Then commercials, short films and acting classes followed. My San Diego acting coach, Terry Ross, encouraged me to move to Hollywood and give it a real try, so I did. I took every risk I could to gain experience and learn the entertainment business…lots of CRAZY experiences, but lots of great breaks and people came out of those risks and continue to, to this day.
Alright, so let’s move onto what keeps you busy professionally?
I am am a stand-up comedian, actress, writer and model. I am most proud of some major TV pilots that did not make it to air and one in the works (crossing my fingers hard). Fellow artists will understand that even if the greater world does not see the end result, the journey and the privilege to create with other talented artists is the accomplishment. I am living my dream. Entertainment doesn’t have a guide book, so in my opinion, there is no other way to get experience than taking every chance you can get and making the most of each opportunity and connection. Be kind. You never know who you will encounter in the future. With all of that said, don’t be afraid to fail or be disappointed. You will. I had so many crazy things happen along the way, including dozens of broken promises and scams. You really have to be okay with enjoying the moments, letting some go and looking forward to the next. When I got into stand-up, I was fortunate to have so many supportive friends and artists around me. I had one award-winning stylist, Maryl Velbeck, that was doing my hair submit me to a magazine she knew as a “celebrity client,” but she said I needed a name. She came up with “The Cougar of Comedy,” which ended up on part of the cover and as a feature. Then, for my 40th birthday, an attorney that I worked with (I have been doing legal work my entire adult life…yes, artists also have to hustle other work), trademarked my comedy name. After that, it was up to me to grow and maintain the brand and my comedy. It couldn’t fit me or my life any better. I genuinely enjoy that the name and persona celebrates the sexuality of a woman as she ages.
If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
In San Diego, I would sip a cocktail on a rooftop in little Italy at Kettner Exchange, have coffee at Caroline’s Seaside Cafe in La Jolla overlooking the coast, brunch at Beaumont’s in Bird Rock, hike above the ocean in Torrey Pines State Reserve, enjoy some music at Humphrey’s by the Bay (preferably by dinghy or standup paddle board), watch some stand-up comedy produced by Up Comedy Shows around the city, take a limo up to Temecula for wine tasting, and do a sunset sail on San Diego Bay.
The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
My agent at the time, Theo Caesar at 90210 Talent, pushed me into my first stand-up spot, because I kept saying “one day.” Not only did I have less than three or four days to prepare a set, it ended up being a competition. I did well, and I caught the bug. Then at one of my very early shows at Flappers, Theo sat front and center and heckled me. He thought he was helping me out. I owe him for my start in stand-up.
(Daniel Graham – Laugh Factory Photo) (Jordan Tolbert – Comedy Banner Photos) (Allison McCoin – Villain Theater) (H2Wu – Studio Photos)