Matt Fleming, A Man Of Many Hats

Matt Fleming

OSWEGO – Matt Fleming is not new to Oswego or the Oswego Players.

In fact, in addition to his current role as director of the Summer musical “Annie Get Your Gun,” he has graced the Frances Marion Brown Theater many times to delight audiences with his comedic timing and hilarious characterizations.

Matt Fleming

Most recently, he played the confused bridegroom in “What the Rabbi Saw,” a shy and retiring boyfriend in “Way Down East,” a frustrated caretaker in “Dracula,’ and himself in “An Act of God” to mention only a few.

Sometimes he has doubled up his time to perform with Theatre DuJour, Oswego’s own interactive dinner theatre company.

He loves the magic of community theater.

So it made great sense when he put on his director’s hat for the first time with Players and started to mold the cast and crew for the production of Irving Berlin’s classic musical.

With a cast of 30 actors, and an additional crew of musicians, tech people, and the like, he found himself in the midst of a very emotional experience.

You see, 23 years ago, he stepped onto a community theater stage for the very first time in a production of “Annie Get Your Gun” in his home town of Binghamton.

Now here is another hat he wears. This spring he took the helm as artistic director for Oswego Players’ Theater Arts Youth Academy.

And with a spring semester under his belt that included the all student produced, comedy, “Snow White and the Queen of Mean,” TAYA is about to begin second semester classes August 10.

He is especially excited about this round of activities with the Youth Academy as 20 students will be participating in a month-long series of Saturday workshops that include a full day spent with the Merry Go Round Theater Company in Auburn.

Thanks to a generous Richard S. Shineman Foundation grant, the group will be able travel to Auburn on August 17 to meet and interact with the cast and crew of MGRT’s production of “South Pacific.”

Working with the dance captain, musical director, and costume designer, the students will get to interact on stage during the day in various activities to sharpen their theater arts skills.

After dinner with the cast, everyone gets to enjoy the full stage performance that night.

Now add to all of this the fact that Fleming has tossed his hat into the political arena.

This spring he decided to run for city of Oswego councilman.

He tells everyone he has come to call Oswego his home and is way proud of the many accomplishments made in recent years and wants to offer his support in any way he can.

However, when you ask him what his favorite role is in life, he doesn’t hesitate telling you, hands down, it’s being uncle Matt to his seven-year-old nephew, Michael.

And it doesn’t take anyone a heartbeat of time to understand how special this particular hat is to him.

Just watch the corners of his mouth shoot upward into an instantaneously huge uncle Matt smile whenever he mentions Michael’s name.

He welcomes everyone to come see this iconic musical. It’s something the whole family can enjoy.

“Annie Get Your Gun” runs its second weekend August 2, 3, 4 in the Frances Marion Brown Theater, Civic Center of Oswego.

Tickets are available online: or can be made by calling the OP box office at 315-343-5138.