Charles Linwood Bailey Sr.

Celebrating The Life and Legacy of Charles “New York Charlie” Bailey

Born in Durham, NC, Dad’s journey took him to New York City, Newark, NJ, and Virginia. He was a loving husband to Joyce, proud father of five sons, and beloved “Poppy” to his many grandchildren. Dad was also a devout Christian and a man of strong faith. As a member of the Church House of God, he believed deeply in God and carried his Christian faith throughout his life. Today, while our hearts are heavy, we find comfort in knowing that the God he believed in and served has called him home.

Some people simply pass through this world, while others leave a presence so strong that their name, their stories, and their spirit continue to live on long after they are gone. Charles Bailey, affectionately and widely known as “New York Charlie,” was one of those unforgettable people.

Charles was born on July 2, 1941, in Durham, North Carolina. His life’s journey would take him from North Carolina to New York City, and later to Newark, New Jersey, where he met the woman who would become his wife, Joyce Bailey. Together, they built a life and a family.

Charles was the proud father of five sons: Sylvester Anderson, Shawn Bailey, Hassan Bailey, Aaron Bailey, and Charles Bailey Jr. He was also blessed with many grandchildren who loved him dearly and affectionately knew him by one of his most treasured names—“Poppy.”

But to countless others, he was simply known as New York Charlie.

And if you knew New York Charlie, you knew there was only one.

Charles possessed a natural charm and charisma that drew people to him wherever he went. He had a way of making his presence felt without ever having to announce himself. His personality could brighten a room, his humor could make people laugh, and his spirit left an impression on nearly everyone fortunate enough to cross his path.

His name rang bells.

From New York City to Newark, New Jersey; from Washington, D.C. to Charlottesville, Virginia; and throughout Fluvanna County, somebody always seemed to know New York Charlie.

Everywhere he went, Charlie knew somebody—and somebody knew Charlie.

Charles truly enjoyed life. He loved music, dancing, and singing, and he had a special love for the music of James Brown. When James Brown came on, those who knew Charlie knew there was a good chance he was going to sing, dance, or do a little bit of both.

Charles was also a man who believed in looking his best.

He took tremendous pride in the way he dressed and carried himself. Being sharp wasn’t just something Charlie did—it was part of who he was. His clothes had to be right, his appearance had to be right, and he had a saying that his family and friends will forever associate with him:

“Cleaner than the Board of Health.”

That was New York Charlie.

Sharp. Confident. Charismatic. Charming. Full of life. And always unmistakably himself.

But behind the clothes, the music, the dancing, the laughter, and that larger-than-life personality was something even more meaningful: a family man whose greatest legacy can be found in the generations that follow him.

To his sons, he was Dad.

To his grandchildren, he was Poppy.

And to so many others, he was a friend and a man they would never forget.

Charles’ children and grandchildren will carry with them memories that no passage of time can erase—the sound of his voice, his expressions, his stories, his laughter, his style, his favorite sayings, and those special little things about him that simply could never be duplicated.

A father’s legacy does not end when he leaves this earth. It continues through his children, his grandchildren, and every generation that follows. And the legacy of Charles Bailey is one that will continue.

On August 1, 2026, Charles completed his earthly journey. Today, however, we gather not only to mourn his passing, but to celebrate the life of New York Charlie.

We celebrate the boy born in Durham, North Carolina, who went out into the world and made his presence known.

We celebrate the man who made his way to New York.

We celebrate the man who found love and built a family.

We celebrate a husband.

We celebrate a father of five sons.

We celebrate Poppy.

We celebrate the sharp-dressed man who always wanted to be “cleaner than the Board of Health.”

We celebrate the man who could hear James Brown and still feel the music.

We celebrate the charm.

We celebrate the dancing.

We celebrate the singing.

We celebrate the laughter.

We celebrate the stories.

We celebrate a personality that was truly one of a kind.

And most importantly, we celebrate a man who will never be forgotten.

There will never be another New York Charlie.

His earthly journey may have ended, but his story did not.

Every time his family gathers and someone tells one of those old Charlie stories, his memory will be there.

Every time James Brown comes on and somebody remembers how Charlie used to move, his spirit will be there.

Every time someone gets dressed from head to toe and proudly says they’re “cleaner than the Board of Health,” Charlie will be there.

Every time one of his grandchildren smiles while telling a story about Poppy, Charlie will be there.

And every time his sons look at their own children and grandchildren, they will be reminded that their father’s legacy continues through them.

Because a man is never truly forgotten when his name is still spoken, his stories are still told, his lessons are still carried, and his love continues to live within the people he leaves behind. One thing is certain:

The name New York Charlie will continue to ring bells.

From Durham to New York.

From Newark to Washington, D.C.

From Charlottesville to Fluvanna County.

And most importantly, in the hearts of his family forever.

Charles was preceded in death by his mother Dorothy Dickey, father Arthur Bailey, son Aaron Jason Bailey, brother Arthur Bailey II, sisters Toni Holmes, Sheila Hill, and Patricia Dickey.

Charles leaves to cherish his memories; the love of his life for over 60 years Joyce Martin Bailey (Bae Bae), four sons Hassan Bailey (Shawna), of N.C., Shawn T. Bailey (Kristie) of Charlottesville, VA, Charles Linwood Bailey, Jr. (Sonnika) of Fluvanna, VA, and Sylvester Anderson of Fredericksburg, VA, brother-in-law Anthony Martin Palmyra, VA, sister-in-law Linda Freeman Newark, NJ, stepfather George Dickey, Richmond, VA., 14 grandchildren and 17 great-grandchildren and a host of nieces and nephews.

Rest peacefully in the arms of the Lord, Daddy. Until we meet again. Charles “New York Charlie” Bailey.

A funeral service to honor Mr. Bailey will be held 1:00pm Sunday, August 16th, at Fluvanna County High School Auditorium, 1918 Thomas Jefferson Parkway, Palmyra, Virginia. Internment will take place immediately following funeral services at Martin Family Cemetery, 142 Martin Lane, Palmyra, Virginia. Repast will be held at Fluvanna County High School following funeral services.

He is in the care of Sheridan Funeral Home.