Rising Stars: Meet Jill Benjamin

Jill Benjamin is a Chicago native who trained and performed improv at Chicago’s IO and The Second City. She then moved to Amsterdam in the late 90’s to work as a performer at the famed comedy theater Boom Chicago. There she met Seth Meyers and toured the world with their two-person show “Pick-ups & Hiccups.” Meyers and Benjamin performed 4 years at the Edinburgh Fringe Festival, the West End in London, in Singapore, NY, Chicago, and LA.

After moving to LA in 2003, Benjamin created a comedy variety show called “Wizard Finger” and cast her friends to tell true stories while fire dancers, musicians, and artists entertained the crowd. For 21 years, she has been acting in commercials and on TV shows, such as History of the World Part II, American Auto, and on the longest-running live-action TV show on Nickelodeon called “Henry Danger” as Henry’s oddly shaped teacher named “Miss Shapen.”

During the strike, Benjamin decided to focus on her second passion: Event Producing. She was asked to plan her friend’s 50th birthday parties, Boom Chicago’s book signing, Brendan Hunt’s Ted Lasso screening at The London, and an after-party for Seth Meyers. She side-hustled to build her portfolio and started @jillbenjaminevents on Instagram to showcase her talent. She networked at events, posted her resume on LinkedIn, and was contacted by Masha Berenboym, owner of Artists Creating Entertainment (ACE).

Jill Benjamin is the Account Sales Manager at ACE and is most proud of pitching the NFL her ideas on theatrical and creative “Way Finding” for ticket holders to enter the stadium at the 2024 Super Bowl in Vegas! They wanted “Roman” theme elements, and she suggested Feather girls with the colors of the feathers to showcase the color-coded entrances, stilt walkers in golden dresses, and living statues to represent beauty, feminine, and power…which was inspired by Madeline Kahn’s character in the Mel Brooks’ movie “History of the World.”

Currently, Jill Benjamin can be seen on a Hilton commercial which also ran the night of the Super Bowl. Her two worlds colliding with acting and producing events. It was her experience in producing her comedy shows, supportive friends, and utilizing her skills in improv that taught her how to think quick on her feet, pitch innovative ideas, and to help pay it forward. She now books her friends as entertainment for events like she did 20 years ago in Wizard Finger.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
The biggest challenge in LA is seeing a lot of your friends gain success while you find yourself in the “waiting game.” I don’t want to wait anymore. I had to analyze what I like the most about what I do best. I can entertain a crowd, and I can create the vibe for a good time. I’ve always had a knack for bringing people together (and being friends with improvisers who are the funniest people in the world makes it a pleasure to throw a party!). For instance, on my 40th birthday I had everyone dress up like the famous person that shares their birthday. My birthday is May 20th, so I was dressed as Cher and all my creative friends really committed to the theme. Few pics can be seen on @jillbenjaminevents. The biggest obstacle I had was being out of the full-time workforce for 12 years to raise my two kids. After a divorce, I’m incredibly proud to find the positive aspects of returning the focus on me. My biggest piece of advice I’d give a woman about to have kids is to NEVER stop creating and working. I pieced myself back in more ways than one and am very excited to see what else is ahead of me in my new chapter.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
At Artists Creating Entertainment, we are just that…artists who are creating the entertainment at an event. If you tell me you’re having an Old Hollywood themed art event, I can walk you through the vision as a guest will see it and how we can make it more impactful. For example, the mood should start once you get out of your car. This is the “Way Finding” moment when a stilt walker in a long golden dress greets you as you hear the sounds of a violinist playing in the distance. As you enter the party, you see a 7-foot red dress cascade down a staircase as the violinist is accompanying the DJ. An art gallery (aka the “Peep Hole” wall we set up), has a white glove pop through a frame as someone’s hand offers you a glass of champagne. As you look at the art, you push aside a picture and peep through to see a burlesque dancer pulling up her stockings in her boudoir. She catches you and blows you a kiss. Then, the guest is approached by a roaming character from the 1920’s and tells you someone has been murdered. Without you knowing, you’ve entered into a Murder Mystery and watch it unfold in an immersive experience. Then,“Walking Art” emerges with people dressed as famous artwork walk by you with picture frames around their top half replicating “The Scream” or “Van Gogh.” Next you see an opera singer in a picture frame singing while someone is painting live art on her dress. This is what we do at ACE!

Who else deserves credit in your story?
@artistscreatingentertainment owner for 10 years, Masha Berenboym for taking me on at ACE and creating all the custom costumes that help pitch these brilliant ideas

My parents for creating the best birthday parties for me that inspired me on my path