Society sparkler Gloria Vanderbilt turned 95 on February 20th. From the day she was born, glossy snapshots chronicling her life have been laminated into our pop-culture.

The Vanderbilt name prompts vapid images of the Gilded Age, a time when the pursuit of happiness focused on following the sun to the next self-indulgence. Members of the Vanderbilt family have led lives with a pedigreed patina, but there has always been more to Gloria than gloss. Her remarkable life’s story includes equal measures of privilege and psychological agony. Tested by fire, she remains an optimist with a badass work-ethic and sound advice for anyone who has ever loved.

The Vanderbilt story has humble roots. Great-great grandfather Cornelius (1794-1877)  grew up poor. Vanderbilt’s success began after quitting school at eleven to help his father ferry freight and passengers between Staten Island and Manhattan (Known today as the Staten Island Ferry). Resourceful when challenged the rough-around-the-edges, the boy nicknamed ‘the Commodore’ quickly learned how to manage and then monopolize large shipping businesses.

In his later years, Vanderbilt connected ships to interstate railroads that helped shape American enterprise. His self-taught business savvy landmarked expansion opportunities across the United States. The Republican entrepreneur who owned or controlled most of the Nation’s transportation lanes earned a legendary fortune but chose to live a relatively modest life.

Some of his money established Nashville’s Vanderbilt University, funded several churches and indulged the many whims of his thirteen children. By today’s standards the Commodore’s wealth at the time of his death was estimated to be $215B. Believing only one of his sons would be capable of managing the family businesses, Cornelius left a stipend to his daughters and most of the estate to his son William and his four sons, William II, Cornelius II, Alfred, and Reginald.

Gloria and Wyatt in Nantucket.

Gloria Vanderbilt is the granddaughter of Cornelius II and daughter of his son Reginald Claypoole. In 1923, a 43 playboy Reggie married 17 year-old Gloria Morgan. He died two years later of an excess of privilege. His teenaged wife was left a New York townhouse and some cash but the bulk of his $2.5M estate was inherited by his toddler Gloria and her sister from a previous marriage.

Caught in a scandalous cash for child-custody battle between a willful mother and artsy aunt Gertrude Vanderbilt Whitney, Gloria grew-up litigated into loneliness. Frenzied media devoured salacious details of family power plays laced with lesbianism like mind-candy. Gloria’s childhood was spent shuttling between mansions with her beloved Nanny Dodo. Fearing undue influence over the little girl, the emotionally bankrupt family eventually dismissed Dodo, depriving the pre-pubescent of the only maternal comfort she had known since birth.

Gloria and her nanny, Dodo.

The absence of a loving family may explain a few of Ms. Vanderbilt’s eyebrow-raising affairs with Hollywood’s glitterati. She married early and often until she settled down in 1963 with her fourth husband Wyatt Cooper.  With Cooper she led a loving and family-centric life. Together they had two sons, Carter and Anderson.

Unexpectedly, Wyatt died in 1978 from heart disease at 50. Without explanation, Carter jumped to his death, in front of his mother from their penthouse balcony in 1988 at age 23.  Anderson Cooper, a contributor to 60 Minutes and host of CNN’s AC 360 said his work today is, in part, a testimony to the suffering of others, honoring the language of pain he understands so well.

Gloria poses with her son, Anderson Cooper of CNN and 60 Minutes.

Four years ago, 91 year-old Ms. Vanderbilt had an upper-respiratory infection. Fearing the inevitability of his mother’s passing in another ‘state of unfinished-ness’ Anderson engaged the ethereal icon in an exploration of their lives.  “The Rainbow Comes and Goes,” and a companion HBO documentary, “Nothing Left Unsaid” are autobiographical bookends of that year-long conversation. The duo’s collaborations serve as manor-sized windows granting anyone interested a voyeuristic glimpse into the metronomic saga of the American family synonymous with success and suffering.

Speaking with the candor of adults, the book and documentary are psychologically dense and visually stunning. The currency between mother and son exchange their interpretations of loss and what life feels like without dependable emotional intimacy. Although there is nothing new in human sexuality, Gloria’s provocative remembrances are remarkable for their lack of parental boundaries with her son. As the perpetually mahogany-haired one reviews lovers, her chalk haired son cringes and wonders if the lack of heart-felt connection fuels their mutual internal rage, constant fear of abandonment and all-consuming work ethics.

The book and documentary explain after her mother, lawyer and psychiatrist drained much of her inheritance Gloria’s intense work-ethic drove her life as an actress, author and fashion designer.  Today, Ms. Vanderbilt continues to work in her studio creating primitive studies of romanticized bliss and longing. In the documentary, Anderson sees her creations as a therapeutic way to “get it out”.

Christopher Madkour, the Executive Director of Alabama’s Huntsville Museum of Art, is also the curator of Gloria Vanderbilt’s private collection. He invited me on a personal tour of her Upper East Side home to see some of her collection and experience, in a small way, the modest life she lives today. Stepping into a magenta foyer framed by black lacquer moldings, lit by a small chandelier, the warmth of her home’s bold originality and sparkle spoke volumes about Ms. Vanderbilt’s resourceful-when-challenged nature.

The highly refined space is a juxtaposition of mirrors that super-imposes guests onto the paintings of Ms. Vanderbilt’s oldest and newest treasures.  Floor to ceiling paintings of ancestral faces live in all places of the atelier filled with Christian and Buddhist iconography and Lucite dream-boxes that surround flea-market dolls adorned with glitter. Echoing throughout the time-stamped gallery of artistic intimacies are variations on themes of Mother and Child.

Following Mr. Madkour down a sterile staircase into Ms. Vanderbilt’s studio, colorful images of love stand sentinel against the walls. A youthful painting of Wyatt’s swagger rests near a painting of beloved Dodo forever holding little Gloria’s hand. Newer works are multi-medium, dreamscapes of lovers and longing.

Ms. Vanderbilt’s habit is to work daily in her no-frills studio creating works to sell on her Instagram account. (@gloriavanderbilt)

Breaking at noon for a peanut butter and jelly sandwich Gloria returns to work at her easel where a bust of the father she never knew over sees her progress in acrylic, pencil or collage.

Before ending the tour of this living legend’s home we returned up-stairs to the living room upholstered in earth and jewel tones. Mr. Madkour pointed out a fireplace hand-painted by Ms. Vanderbilt that includes the quote “Be kind for everyone is fighting a battle you may not see.” The simplicity of the sentiment focused the greater meaning of the extensive art collection, the book and the HBO documentary.  Together they are an unambiguous running-dialogue of Gloria Vanderbilt’s 95 years. With Anderson Cooper’s help each piece can be seen as part of their puzzling life of privilege and pain.

Gloria’s uniquely American story is a reminder of life’s fragility and an inspiration to leave loved ones with “Nothing Left Unsaid”.

Nothing Left Unsaid is available on demand on HBO.

Diane Kilgore is a journalist in the Greater Boston Area. She is a Cultural Contributor for NewBostonPost and creator of the lifestyle blog ‘To Di For.’