Inside Ashton Kutcher's Close-Knit Circle: Diddy, Danny Masterson, and Beyond

Ashton Kutcher s Inner Circle Diddy Danny Masterson and More

Ashton Kutcher and Danny Masterson. Todd Oren/WireImage

Some of Ashton Kutcher’s friendships have caused controversy.

Kutcher and Sean “Diddy” Combs have been friends since the early 2000s after meeting on the set of Punk’d.

Ashton Kutcher shared on "Hot Ones" in 2019 that his friendship with Diddy started over a challenge on Punk'd. Diddy initially thought he couldn't be pranked, but Kutcher proved him wrong, leading to a conversation that sparked their fast friendship.

Diddy faced controversy in March 2024 when Homeland Security raided his homes in Los Angeles and Miami. The raid was reportedly related to federal sex trafficking allegations. Diddy has faced previous accusations of sexual assault from multiple individuals, including an allegation from ex-girlfriend Cassie in November 2023. Despite the allegations, Diddy has maintained his innocence and denied all claims.

Kutcher is reportedly expected to be subpoenaed as part of the sex trafficking investigation, per the Daily Mail.

Keep scrolling to see more of Kutcher’s inner circle:

Diddy

Ashton Kutcher s Inner Circle Diddy Danny Masterson and More

Ashton Kutcher and Sean Combs. Stefanie Keenan/Getty Images for WeWork

Kutcher and Diddy met on the set of Punk’d in the early 2000s and have been friends ever since.

“I’ve got a lot I can’t tell,” Kutcher said in a “Hot Ones” interview in 2019 after being asked about Diddy’s parties. “I can’t tell that one either.”

Danny Masterson

Kutcher and his wife, Mila Kunis, befriended Masterson during the filming of That ‘70s Show from 1998 to 2006. They later worked together on the Netflix series The Ranch until Masterson was removed from the show in 2017 due to allegations of sexual assault by multiple women. In June 2020, Masterson was arrested and charged with three counts of rape, to which he pleaded not guilty. After a mistrial in November 2022, Masterson was ultimately found guilty of two counts of forcible rape and sentenced to 30 years in prison in September 2023.

In September 2023, it was revealed that Kutcher and Kunis had written a letter of support to Judge Charlaine F. Olmedo before Masterson's sentencing.

Kutcher wrote in a letter obtained by The Underground Bunker that Danny has always been a positive influence on him. Over their 25-year friendship, Kutcher never remembers Danny lying to him. Danny taught Kutcher about facing problems directly, resolving them, and moving forward in life and relationships.

After receiving criticism for their supportive letters, Kunis and Kutcher went on Instagram to clarify why they wrote them.

"We understand the pain caused by the character letters we wrote for Danny Masterson," he mentioned in the video. "A few months back, Danny and his family requested us to write character letters to show the person we have known for 25 years, for the judge to consider during sentencing."

Kutcher clarified that the letters were solely meant for the judge to review and were not intended to discredit the victims' testimonies or cause them further trauma.

Reese Witherspoon

Ashton Kutcher s Inner Circle Diddy Danny Masterson and More

Reese Witherspoon and Ashton Kutcher became good friends while working together on the romantic comedy Your Place or Mine, which premiered on Netflix in February 2023.

Michael Kutcher

Reese Witherspoon praised Michael Kutcher in a January 2023 interview with Esquire, highlighting his deep love for his family and his dedication as a dad. She mentioned that Michael shows up every day for his kids without any pretense, exuding comfort in his own skin. Witherspoon also noted that Michael is hysterically funny.

Ashton Kutcher s Inner Circle Diddy Danny Masterson and More

Michael Kutcher and Ashton Kutcher. Adam Bettcher/Getty Images for Starkey Hearing Foundation

Ashton and his twin brother, Michael, had grown apart for several years, but they have now developed a stronger bond.

During an episode of The Checkup With Dr. David Agnus in December 2022, Ashton shared a key moment that changed their relationship. When Ashton was gaining success in his career in New York, Michael visited him and expressed, “Every time you feel sorry for me, you make me less.” Michael continued, “This is the only life I’ve ever known, so stop feeling sorry for the only thing I have.” This conversation led to a shift in their relationship, bringing them to a place where they see each other as equals.

Thomas Rhett

Ashton Kutcher s Inner Circle Diddy Danny Masterson and More

Ashton Kutcher and Thomas Rhett. Denise Truscello/ACMA2018/Getty Images for ACM

Kutcher, a longtime country fan, connected with Rhett during a country music festival.

Rhett shared in a blog post to his record label, Big Machine Records, in March 2019 that he was surprised to learn that Ashton Kutcher was a fan of his music. They ended up forming a relationship, and Rhett and his wife were invited to dinner by Kutcher and his wife, Mila Kunis, in Los Angeles.

During dinner, Rhett and his wife were amazed at the idea of dining with the celebrity couple. They hit it off immediately and have since become "decently close" friends with Kutcher and Kunis.

He added that he never would have imagined that one of his favorite actors would be a fan of his without ever meeting before.

In May 2022, Kutcher even joined Rhett on stage during his Stagecoach set.

Dax Shepard

Kutcher and Shepard met on the set of Punk’d and reunited several years later when both their wives, Kunis and Kristen Bell, costarred in the 2016 comedy, Bad Moms.

"Dax and I showed up and brought them flowers. It was funny because it sort of reignited our friendship. We had worked together on Punk'd many years ago, and after spending time together on the show, we realized how much we enjoyed each other's company," Kutcher shared during a December 2018 interview on The Ellen DeGeneres Show. He mentioned that he then asked Shepard to join him on The Ranch, and now they spend time together every day.

Editor's P/S:

Ashton Kutcher's friendships have drawn attention due to controversies surrounding some of his associates. His close ties with Sean "Diddy" Combs,