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A complete timeline of Ashton Kutcher's friendship with 'That '70s Show' costar and convicted rapist Danny Masterson

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Ashton Kutcher, Mila Kunis, and Danny Masterson in 2000Chris Weeks/Getty Images
  • Ashton Kutcher was criticized for writing a letter of support for Danny Masterson after Masterson was convicted of rape.

  • Kutcher called Masterson an "excellent role model" in a letter to the sentencing judge.

  • Here's a timeline of their friendship, which spans over two decades and two sitcoms.

Ashton Kutcher and Danny Masterson played friends on Fox's hit late '90s sitcom "That '70s Show."

But the actors appear to have forged an even closer bond in real life when the cameras weren't rolling.

Earlier this year, Masterson was convicted of raping two women, but Kutcher and his wife Mila Kunis have seemingly stood by their old costar. The pair came under fire after it was revealed they'd written letters of support for Masterson in advance of his sentencing. Here's a timeline of Kutcher and Masterson's 25-year friendship.

1998: Kutcher and Masterson met and bonded over an inappropriate bet involving Kutcher's now-wife Mila Kunis

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Ashton Kutcher, Mila Kunis, and Danny Masterson in 2000Chris Weeks/Getty Images

Masterson and Kutcher met in 1998 while filming the pilot episode of the hit Fox sitcom "That '70s Show" with Kutcher's now-wife Mila Kunis. Masterson was 22, Kutcher was 19, and Kunis was 14.

In the wake of the couple sending individual letters of support for Masterson prior to his rape sentence, a clip from "The Rosie O'Donnell Show" resurfaced online in which Kunis and Kutcher —who played love interests on-screen — told O'Donnell that Masterson dared Kutcher to French kiss Kunis during their first onscreen kiss, and that he'd give him $10 to do it.

The costars disagreed about whether Kutcher followed through with the bet. "I didn't let him, I think he tried," Kunis said.

Kutcher admitted to O'Donnell that even scripted kisses between the characters were "slightly illegal" at the time, presumably considering Kunis's age.

2002-2003: Masterson and Kutcher could often be found partying together

Danny Masterson, Ashton Kutcher, and Joe Francis.
Danny Masterson, Ashton Kutcher, and "Girls Gone Wild" founder Joe Francis in 2003.Michael Caulfield Archive/Wireimage

In 2002, they traveled to Costa Rica together to attend the opening of a new casino and resort (replete with performances from the Pussycat Dolls and Carmen Electra).

Masterson and Kutcher were often each other's plus-ones to movie premieres when they were unattached, and Masterson supported Kutcher's burgeoning film career by attending the premiere of his 2002 film "Just Married."

The pair competed in the 2003 NBA All-Star game together, and as recently as 2016, they hung out together at the Wynn Casino with Masterson's brother Jordan and some of their "The Ranch" castmates.

2003: Masterson and Kutcher invested in a now-defunct restaurant together

Ashton Kutcher talking to Puff Daddy and Danny Masterson at Dolce
Ashton Kutcher talking to Puff Daddy and Danny Masterson during the 2003 MTV Movie Awards afterparty at Dolce.Chris Weeks / Getty Images

In 2003, both Masterson and Kutcher invested in the Italian eatery Dolce, alongside their "That '70s Show" costar Wilmer Valderrama.

The restaurant, developed by "Big Brother" winner Mike "Boogie" Malin, was a West Hollywood hotspot when it first opened, but closed in 2009.

2003 and 2004: Kutcher supported his costars, including Masterson, at a Church of Scientology holiday event

Kutcher and Masterson at Scientology's Celebrity Centre on December 4, 2004 in Hollywood, California.
Kutcher and Masterson at Scientology's Celebrity Center on December 4, 2004, in Hollywood, California.Getty Images for COS

Both Masterson and his "That '70s Show" costar Laura Prepon were members of the Church of Scientology in the early 2000s.

Kutcher's personal ties to the organization are unclear. Although he has never publicly identified as a Scientologist, there is photographic evidence of the "Dude, Where's My Car?" star performing on stage at the Church's annual "Christmas Stories" event to benefit the Hollywood Police Activities League in 2003 and 2004.

Kunis, Prepon, and Valderrama also attended the event for two consecutive years.

Prepon revealed that she was no longer a Scientologist in a 2021 interview with People. Masterson is believed to be still involved in the Church; during his rape trial, his victims accused Scientology of trying to silence them, an accusation the Church has denied.

2005: Masterson appeared on Kutcher's hit prank show 'Punk'd.'

Danny Masterson on "Punk'd."
MTV/Paramount Media Networks

Kutcher co-created and hosted MTV's hit show "Punk'd" from 2003 to 2007.

On a season six episode of the show, Kutcher got Masterson involved in a tricky situation involving stereo equipment falling from a moving truck.

Kutcher planted actors to be the truck driver and strangers on the street who steal the speakers. He was operating under the assumption that Masterson would be too good a person to drive away from the fallen equipment or steal it. Instead, Kutcher thought his friend might stick around to clean up and discourage the strangers from stealing.

While introducing the scenario, Kutcher called Masterson a "very moral man" and predicted that he wasn't going to steal the equipment because he was "not gonna be the one to pull the crooked move, he's a straight and narrow guy."

Masterson did, in fact, discourage Kutcher's plants from stealing boxes of speakers and tried to break up a fight on the scene when the fake truck driver came back angry about his stolen goods.

2006: 'That '70s Show' aired its series finale

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Cast members of 'That '70's Show' celebrate the show's 100th episode in April 2002 in Los Angeles.Getty Images

The series finale of "That '70s Show" aired on Fox on May 18, 2006.

"I've actually never cried so much in my life," Masterson told Access Hollywood at the wrap party, as he recalled filming the episode.

2016: A decade after 'That '70s Show' ended, Masterson and Kutcher reunited on Netflix's 'The Ranch'

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Ashton Kutcher and Danny Masterson on Netflix's "The Ranch."Netflix

Kutcher and Masterson played brothers Colt Bennett and Jameson "Rooster" Bennett, respectively, on Netflix's sitcom "The Ranch" from 2016 to 2017.

In a joint interview promoting the show in 2016, Kutcher told On Demand Entertainment that they'd been looking for a project to work on together since "That '70s Show" wrapped and spent a year developing their characters.

While promoting the show on "The Late Late Show with James Corden" that same year, Masterson jokingly told Corden that he had naked pictures of Kutcher from the old days partying together while they worked on "That '70s Show."

2017: Masterson was written off of 'The Ranch' amid sexual assault allegations against him

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Masterson was accused of sexual assault in 2017. Getty Images

After accusations of rape emerged against Masterson in 2017, his character Rooster was written off of "The Ranch" in an episode during the second half of season three.

"As a result of ongoing discussions, Netflix and the producers have written Danny Masterson out of 'The Ranch,'" Netflix said in a statement to Insider at the time. "Yesterday [Monday] was his last day on the show, and production will resume in early 2018 without him."

In his own statement at the time, Masterson told HuffPost he was "disappointed" with the streamer's decision.

"I have never been charged with a crime, let alone convicted of one," his statement continued.

Kutcher didn't speak on the allegations at the time.

On Materson's final episode of "The Ranch," released on June 15, 2018, Rooster flees town after he's threatened by his girlfriend's ex at gunpoint.

January 2023: Kutcher speaks out about Masterson's charges for the first time

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Ashton Kutcher at the 2023 Milken Institute Global Conference.Jerod Harris via Getty Images

Kutcher spoke about the charges against Masterson for the first time in an Esquire interview published in January.

At the time, Kutcher said he wanted his friend and mentor, who had kept him away from drugs during his early years of fame, "to be found innocent of the charges brought against him."

"I'm not the judge. I'm not the jury. I'm not the DA. I'm not the victim. And I'm not the accused. And so, in that case, I don't have a space to comment," he continued.

Kutcher said he felt bad that Masterson's 9-year-old daughter, Fianna Francis Masterson, whom he shares with wife Bijou Phillips, was going to have to read about her dad's case online eventually.

Kutcher also revealed that he still talked to Masterson and his brother.

He also expressed support for Masterson's accusers. "I wholesale feel for anybody who feels like they were violated in any way," he said.

September 8, 2023: Kutcher and his wife Mila Kunis write letters of support for Masterson prior to his rape sentencing.

Ashton Kutcher and Mila Kunis at the 2022 Oscars.
Ashton Kutcher and Mila Kunis at the 2022 Oscars.Kevin Mazur / Contributor / Getty Images

Masterson was convicted of raping two women in May 2023 and sentenced to 30 years in prison on Thursday, September 7.

On September 8, legal affairs journalist Meghann Cuniff was the first to publish individual letters of support that Kutcher and Kunis, who married in 2015, wrote Los Angeles Superior Court Judge Charlaine F. Olmedo in support of Masterson's character.

In his letter, Kutcher wrote of Masterson: "We have spent countless hours together with our kids and he is among few people that I would trust to be alone with my son and daughter."

He also called his former co-star a role model and credited Masterson with keeping him away from drugs.

In the letter, Kutcher said he knew Masterson had been found guilty of two counts of rape and that "the victims have a great desire for justice," but asked the judge to consider his daughter and character in sentencing.

September 9, 2023: Kutcher and Kunis issue a public apology for their letters supporting Masterson

After a public outcry, Kutcher and Kunis posted a video to Instagram apologizing to Masterson's victims and explaining their actions one day after their letters were published online.

In the video, Kutcher explained that Masterson's family had reached out to them and asked for character letters describing the man they had known for 25 years.

"They were intended for the judge to read and not to undermine the testimony of the victims or retraumatize them in any way. We would never want to do that and we're sorry if that has taken place," Kutcher said of the letters in the video.

Read the original article on Insider