Jean Smart arrived at the 2026 Emmy Awards with someone particularly special by her side.
Instead of walking the carpet with a fellow actor or Hollywood date, the 75-year-old Hacks star brought her younger son, Forrest Gilliland, offering fans a rare glimpse of the teenager she largely raised away from the spotlight.
The mother and son posed together ahead of the September 14 ceremony at Los Angeles’ Peacock Theater, where Smart would go on to make Emmy history. Reuters footage from the arrivals confirms Forrest accompanied his mother on the carpet. (Reuters Connect)
And for those who remember him as the little boy Smart and her late husband, actor Richard Gilliland, welcomed into their family years ago, seeing him nearly grown was a striking reminder of how much time has passed.
Forrest Is the Younger of Jean Smart’s Two Sons
Smart and Gilliland raised two children together.
Their eldest son, Connor, was born in October 1989. Nearly two decades later, the couple expanded their family through adoption, welcoming Forrest from China. Contemporary profiles place Forrest’s arrival with the family in 2009, with the adoption publicly announced in January 2010. (People.com)
Smart has recalled the moment Forrest was placed in their arms with enormous affection.
“The second this baby was handed to us, we were just so besotted,” she told Glamour in a comment subsequently quoted in coverage of his 2026 Emmy appearance. She called her youngest child “an amazing person.” (Just Jared)
Now that little boy is a teenager — and increasingly tall enough to stand beside his famous mother as her red-carpet companion.
His Raven-Black Hair Immediately Stood Out
Forrest wore a classic black suit with a white shirt and silver-toned tie for the Emmys, while his dark hair provided a striking contrast to his mother’s blonde locks.
Smart, meanwhile, appeared in a flowing black-and-silver ensemble for one of the biggest nights of her career. (Yahoo News)
The pair smiled together for photographers before entering the ceremony.
Forrest has remained considerably more private than his mother, so appearances like this one remain relatively unusual. He has, however, joined Smart at select events over the years, allowing fans to watch him grow from a child into a young man.
The Evening Became Historic for His Mom
Forrest wasn’t simply attending another awards ceremony.
He was there when his mother achieved a television milestone.
Smart won Outstanding Lead Actress in a Comedy Series for her portrayal of Deborah Vance in Hacks. It was her fifth consecutive win for the role, meaning she won the category for every season of the show’s five-season run. The Television Academy lists Smart as an eight-time Emmy winner overall. (AP News)
But amid the career achievement, Smart made sure her sons were part of the moment.
During her acceptance speech, she thanked both Forrest and Connor, describing her children as her “anchor.” (People.com)
That brief acknowledgment carried additional emotional weight considering what the family has endured together.
Richard Gilliland Died Suddenly in 2021
Smart met actor Richard Gilliland while working on the beloved CBS sitcom Designing Women.
Smart starred as Charlene Frazier Stillfield, while Gilliland appeared on the series as J.D. Shackelford. Their relationship moved beyond the television set, and they married in 1987. (People.com)
Their marriage lasted more than three decades.
Then, in March 2021, Gilliland died at 71 following a brief illness.
Smart was suddenly facing life without the man who had been her husband for 34 years — while Forrest was still young.
She later described becoming a single parent under those circumstances as “unimaginable.” (People.com)
Their Love Story Began on ‘Designing Women’
Long before Hacks introduced Smart to another generation of viewers, Designing Women was one of the projects that defined her early career.
It also changed her personal life forever.
Smart and Gilliland met while working on the series and married in June 1987. Two years later, they welcomed Connor. Nearly 20 years after Connor’s birth, Forrest joined the family. (People.com)
The couple’s marriage became one of Smart’s constants while her acting career moved through sitcoms, dramas, stage work and films.
Gilliland was an actor himself, with credits stretching across television and film, but Smart later acknowledged the compromises he made for her career.
His death therefore changed not only her home life but the partnership that had accompanied most of her adult career.
Connor Stepped Up for His Mom and Younger Brother
Smart wasn’t entirely alone after Gilliland’s death.
Her older son, Connor, was already an adult, and according to People, he moved back home for a period to help his mother and younger brother navigate their new reality. (People.com)
The age difference between the brothers is considerable — almost two decades.
But the unusual family dynamic appears to have provided Smart with an important support system at a time when Forrest was still growing up.
Smart has largely kept both sons outside the celebrity machine, particularly compared with the amount of attention surrounding her own career.
Forrest’s latest appearance therefore offered an uncommon window into that part of her life.
Forrest May Have Caught the Acting Bug
Interestingly, the youngest Gilliland may eventually follow his parents into performing.
Recent reporting says Forrest has shown an interest in acting and participated in a theater production at his high school. (People.com)
With two actors as parents, the connection isn’t exactly surprising.
But Smart hasn’t pushed her son into Hollywood.
Instead, his upbringing has remained relatively private, with occasional awards-show appearances offering only brief glimpses of him.
Whether acting becomes a career or simply something Forrest enjoys remains his story to decide.
For now, he appears content supporting his mother.
Smart’s Career Has Reached New Heights in Her 70s
There is something remarkable about the timing of Forrest’s teenage years and Smart’s career.
Rather than slowing down as she entered her 70s, the actress experienced one of the most celebrated periods of her professional life.
Her performance as comedian Deborah Vance in Hacks earned extraordinary critical recognition. By September 2026, Smart had accumulated 15 Emmy nominations and eight wins across her career. (Television Academy)
Hacks concluded its five-season run in May 2026, making this year’s Emmy ceremony particularly meaningful. (AP News)
And on the night Smart closed that chapter with another trophy, Forrest was sitting nearby.
Five Years After Losing His Dad, Forrest Stood Beside His Mom
That is ultimately what makes the photographs more than another celebrity mother-and-son red-carpet moment.
Five years have passed since Richard Gilliland’s death.
Forrest has gone from being a young boy grieving his father to a teenager standing beside his mother during one of the biggest nights of her career.
Smart has simultaneously navigated grief, single parenthood and an extraordinary professional resurgence.
And when she finally stood on the Emmy stage holding another trophy, she didn’t speak only about Hollywood.
She spoke about her children.
Forrest and Connor, she said, are her “anchor.” (People.com)
The cameras may have been focused on Jean Smart that evening, but the rare photographs of the teenager beside her quietly told another story — one about the family that remained behind the celebrated actress after a devastating loss, and the little boy who is now almost all grown up.
For more incredible transformations, see how Demi Moore Stuns With Dramatic Bob After Decades of Signature Long Hair or check out how “The Breakfast Club” Star Judd Nelson Looks Dramatically Different During Rare Outing 40 Years After Becoming an ’80s Heartthrob. And for a truly heartbreaking story, read about the Third Victim in NewsChopper4 Crash Who Wasn’t Even in the Helicopter.
