Chelsea Handler found an unexpected angle in Reese Witherspoon’s birthday tribute to her son Deacon Phillippe. While the actress was celebrating a family milestone, the comedian had a teasing observation about one of their photographs together.
Witherspoon, 50, shared the Instagram carousel on Friday, October 23, as Deacon turned 23. The collection brought together three pictures taken at different stages of his life.
Celebrity friends joined the celebration in the comments. Gwyneth Paltrow remarked on how much he had grown, while Mindy Kaling expressed surprise at his age. Nina Dobrev and Kristin Chenoweth also sent birthday wishes.
Deacon is Witherspoon’s younger child with former husband Ryan Phillippe. They also share daughter Ava, 27. Witherspoon has another son, Tennessee, 14, from her marriage to Jim Toth.
Chelsea Handler Singles Out the Beach Photo
View this post on Instagram
The opening photograph shows Witherspoon and Deacon standing in front of the ocean. Wearing a black dress, she places a hand on his shoulder while he poses beside her in a striped shirt and brown trousers.
Handler wished him a happy birthday before adding, “You two look like a couple in the first slide,” according to Entertainment Weekly.
The other photographs reach further back into their family album. One is a close-up selfie with a much younger Deacon. Another shows Witherspoon wearing a wide-brimmed straw hat beside her son, who has on a cap and sunglasses.
Witherspoon Remembers the Year Deacon Was Born
In her caption, Witherspoon recalled a fire in Los Angeles during the year of Deacon’s birth. She used that memory to describe the light she believes he carries within him and helps other people recognize in themselves. She closed by expressing her love for him and how fortunate she feels to be his mother.
Witherspoon has previously spoken about discovering new rewards in parenting as her children grow older. During a June 2021 conversation with Tracee Ellis Ross for Interview, she described how their conversations had begun helping her understand the world differently.
“I never expected the kind of relationship that I have with them,” she said. There was room for less serious parenting moments, too. Witherspoon told Ross she had been dancing around her kitchen to Top 40 songs to make people laugh, carrying on a habit she remembered from her own mother.
Deacon Worked With Will Ferrell’s Son on a Movie Soundtrack
Deacon’s music career has already intersected with his mother’s acting work. He featured on Magnus Ferrell’s “Slow Down,” released for the 2025 comedy You’re Cordially Invited, which starred Witherspoon and Magnus’ father, Will Ferrell.
Magnus explained how the track reached the movie in an interview with PEOPLE. He and his USC roommate had experimented with an unusual, fast-paced song before setting it aside. After Magnus sent it to his father, Will shared it with the filmmakers, who needed music for a party scene.
His Family Recently Supported His Film Premiere
Witherspoon also supported another of Deacon’s projects last month. She joined Ava and her mother, Betty, at the September 26 Nashville Film Festival premiere of Brother Save Us.
Deacon stars in and executive produces the film, written and directed by Jesse Behrenwald. The story follows brothers trying to keep their family’s farm operating in a dystopian Midwest, where their father introduces an AI-powered robot to help with the harvest.
His screen work also includes Never Have I Ever and Motorheads, the latter alongside his father. Next, he is set to play Michael Young in Netflix’s Better Than the Movies adaptation. Julia Hart is directing the film based on Lynn Painter’s novel.