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Chelsea Handler Jokes Reese Witherspoon and Her Look-alike Son Could Pass for a 'Couple'

Split image of Chelsea Handler and Deacon Phillippe with Reese Witherspoon.
Source: MEGA;@REESEWITHERSPOON/INSTAGRAM

Chelsea Handler teased Reese Witherspoon about a photo with son Deacon Phillippe.

Oct. 25 2026, Published 5:05 p.m. ET

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Chelsea Handler left an unexpected comment on Reese Witherspoon's birthday post for her son, Deacon Phillippe, after the actress shared a series of photos marking his 23rd birthday.

"You two look like a couple in the first slide," Handler wrote beneath the Instagram carousel, after first wishing Phillippe a happy birthday.

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Witherspoon Shared Special Moments With Phillippe

Image of Reese Witherspoon and Deacon Phillippe.
Source: @REESEWITHERSPOON/INSTAGRAM

Reese Witherspoon shared a series of family photos for Deacon Phillippe's 23rd birthday, including a seaside snapshot of the mother and son posing together.

The comedian was responding to a picture of Witherspoon and Phillippe posing together beside the ocean. The actress, 50, leaned against her son's shoulder as they stood side by side, with the image appearing first in the collection.

The post also featured other family snapshots, including pictures from earlier years. Handler singled out the opening image in her comment.

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Witherspoon Shared a Personal Message for Her Son

Split image of Reese Witherspoon and Deacon Phillippe.
Source: MEGA

Reese Witherspoon shared an emotional tribute to son Deacon Phillippe.

The Legally Blonde star marked the occasion with a tribute reflecting on her son's birth and the person he has become.

"Happy Birthday to my son Deacon, who is turning 23 today," the Academy Award-winning actress wrote in the caption. "The year you were born, there was a fire in LA. Raging all around us. Somehow that fire forged you."

She gushed about the qualities she admires in her son. "You were born into the light, you carry it inside you, and you help us see it in ourselves," stated the 50-year-old Hollywood A-lister.

"I love you so much, so lucky to be your mom. 🩵," she concluded.

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The Post Attracted More Birthday Tributes

Image of Reese Witherspoon and Deacon Phillippe.
Source: MEGA

Gwyneth Paltrow and other fans joined Reese Witherspoon's birthday tribute to Deacon Phillippe, sharing warm wishes and affectionate comments about her son.

Celebrities and fans took to the comments section to point out the resemblance between Witherspoon and her son.

"He is your 'mini me'! ❤️," one commenter wrote.

"The same person 😍😍," another added.

"Happy birthday to Deacon," one person wrote, while another commented, "He is a doll! Happy Birthday, Deacon!"

Gwyneth Paltrow also joined the well-wishers, writing, "Happy Birthday, you gorgeous boy! 23. Wow."

Another commenter added, "Oh I forgot to say happy birthday Deacon!😊."

Others kept their messages brief, posting "cutie pie" and "happy birthday."

Phillippe Is Building a Career in Music and Acting

Image of Deacon Phillippe.
Source: MEGA

Deacon Phillippe is pursuing music and acting.

Phillippe is Witherspoon's son she shares with her ex-husband actor Ryan Phillippe. The former couple also shares daughter Ava Phillippe, 27. Reese has another son, Tennessee Toth, 14, with her ex-husband Jim Toth.

Unlike his famous parents, Deacon has focused much of his early career on music. He has released two albums and several singles, including "Slow Down," a track he recorded with Magnus Ferrell, the son of Will Ferrell, for the soundtrack of the 2025 comedy You're Cordially Invited.

He has also pursued acting, making his screen debut in Netflix's Never Have I Ever in 2022. In 2025, he appeared in Prime Video's Motorheads, which also featured his father.

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