Your Regional Guide To The Performing Arts

Skylight Actors Explore Deeper Meaning Behind ‘Annie’

Skylight Actors Explore Deeper Meaning Behind ‘Annie’
Photo Credit: Photo by Mark Frohna

With its heartwarming message and call for a better tomorrow, there’s no better time than now to bring Annie to the Skylight Music Theatre stage. If you were still a wide-eyed, rambunctious child the last time you sang along to the musical’s catchy tunes, like It’s the Hard-Knock Life or Maybe, there’s a good chance the show’s impactful message could have flown way over your head.


“It’s so funny because I haven’t listened to this music in probably 20 years,” said Matt Crowle, who is playing Rooster. “I had no idea about the emotional impact some of these songs had when I was a kid. It really was a lovely surprise to listen to the music in my adulthood and hear it completely different.”


In case you need a refresher, Annie centers on an orphan living in New York during the Great Depression. When millionaire Oliver “Daddy” Warbucks, played by Skylight favorite Andrew Varela, decides to let an orphan live in his home in an attempt to promote his image, Annie, played by both KyLee Hennes and Eloise Field, is selected.


Of course as all great musicals, the events don’t transpire so smoothly. When Mr. Warbucks offers a $50,000 award to anyone that can prove they are Annie’s parents, imposters begin arriving left and right. Two of the most notable posers include Rooster, brother to the evil orphanage director Miss Hannigan (Carrie Hitchcock), and his scheming girlfriend Lily St. Regis (Samantha Sostarich).


                                                                                                  Carrie Hitchcock as Miss Hannigan and Eloise Field as Annnie. Photo by Mark Frohna.

“With everything going on politically and socially right now, you can still draw parallels to the story of Annie,” Crowle said. “There’s a story of survival, but there’s also a very strong message of hope. There’s this little kid with moxie who refuses to be told no and has determination to make everything better.”


In fact, one of the most memorable moments from the story is when Annie unintentionally inspires President Roosevelt and his cabinet members to invent the New Deal—a political tie uncommon in most kids’ shows.


“Here is this remarkable child who has nothing, but remains optimistic,” Hitchcock explained.  “What’s so interesting to me is how these people who are affected variously throughout the show, with these bad circumstances such as financial and gender disparities, choose to precede. Do we come together and acknowledge what we have in common, or do we become even smaller and try to insulate ourselves and fight within ourselves?”


The three villains, Miss Hannigan, Rooster and Lily, are all major driving forces in Annie. For both Crowle and Sostarich, playing a show’s con artist is a new concept. Crowle, a Chicago actor, shared that he is more accustomed to playing the goofy best friend or side kick, like Bert in Mary Poppins at Paramount Theatre or Cosmo Brown in Singin’ In The Rain at Drury Lane Oakbrook. Some of Sostarich’s favorite roles include Lady of the Lake in Monty Python’s Spamalot at Four Seasons Theatre and Fortuna in Fortuna the Timebender vs. The School Girls of Doom at Milwaukee Opera Theatre.



                                                                   Samantha Sostarich as Lily St. Regis, Matt Crowle as Rooster and Carrie Hitchcock as Miss Hannigan. Photo by Mark Frohna. 

Sostarich explained that director Molly Rhode has helped her, Crowle and Hitchcock explore the many different layers of these characters.

“We want to make sure our characters don’t come off like cartoons, which is the easy way to play a villain,” Sostarich said. “We want to give a bit of a back story to make the audience believe these characters are actually good at being grifters. We want the audience to think ‘oh of course they get away with it.’”


Hitchcock on the other hand has played her fair share of villains, including Masha in Vanya and Sonia and Masha and Spike at Milwaukee Chamber Theatre. She said there is a lot of fun in getting to add the conflict in any given show.


Varela, who most recently played the title role in Sweeney Todd on the Skylight stage, will be making the transition from Demon Barber on Fleet Street to loving dad in Annie. Although this may sound like a striking shift, Valera noted that his responsibility as an actor remains the same, which is to create a believable character on stage.


“It’s kind of the opposite of Sweeney Todd where everything is terrible and dark,” Varela said. “In this show it is relentlessly positive and relentlessly upbeat.”


                                                                                  Andrew Varela as Oliver "Daddy" Warbucks and Eloise Field as Annie. Photo by Mark Frohna. 

Varela explained that one of his favorite parts of working at the Skylight is how the creative team allows the actors to really make the characters their own.


“The fact that they allow me to explore the characters and come up with what I want is a gift as an actor,” Varela shared. “I get as gratifying an experience being on the Skylight stage as I do on any Broadway stage.”


Annie runs at Skylight’s Cabot Theatre Nov. 17 – Dec. 27.  For tickets call the box office at 414-291-7800 or visit




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