DIDDY, KUTCHER, AND HOLLYWOOD FRIENDSHIPS: A TIMELINE

BY SNN.BZ STAFF

This article examines the friendships among Sean “Diddy” Combs, Ashton Kutcher, Jamie Foxx, Danny Masterson, and Wilmer Valderrama, their shared Hollywood history, and recent legal developments involving Combs and Masterson.

Background Context

Sean “Diddy” Combs was arrested in September 2024 on charges of racketeering, sex trafficking, and transportation to engage in prostitution. He is detained without bail at the Metropolitan Detention Center in Brooklyn, with a trial scheduled for May 2025. Ashton Kutcher, a friend of Combs from the early 2000s, has faced public attention due to their past association. Separately, Kutcher and his wife, Mila Kunis, received criticism in 2023 for writing character reference letters for Danny Masterson, their former That ’70s Show co-star, who was convicted of rape.

Kutcher and Masterson’s Legal Controversy

In 2023, Danny Masterson was convicted of raping two women between 2001 and 2003 and sentenced to 30 years in prison. Kutcher and Kunis wrote letters to the court describing Masterson’s positive character, which became public and sparked backlash due to Masterson’s crimes.

The couple later apologized, stating their intent was to support a friend, not to undermine the victims. Masterson, a member of the Church of Scientology, faced allegations from accusers that the Church attempted to suppress their claims, though these claims are part of ongoing legal proceedings and not fully substantiated here.

Combs and Kutcher’s Friendship

Ashton Kutcher and Sean Combs developed a friendship in the early 2000s, notably during Combs’ time hosting Making the Band on MTV and Kutcher’s rise with That ’70s Show and Punk’d. The two collaborated on projects, including Combs’ appearance on Punk’d in 2003, and were photographed together at events like Combs’ White Parties.

In a 2019 Hot Ones interview, Kutcher referenced attending Combs’ parties but did not provide details. Sources close to Kutcher have stated he has had minimal contact with Combs in recent years and has no involvement in Combs’ legal issues.

The “New Rat Pack” Context

In a 2003 New York Times article, Combs, Kutcher, and Jamie Foxx were described as likening themselves to a modern version of the original Rat Pack (Frank Sinatra, Dean Martin, Sammy Davis Jr.) due to their friendship and social prominence in Hollywood. No formal group named “The New Rat Pack” was officially documented, but Kutcher, Combs, Foxx, Masterson, and Wilmer Valderrama, who were friends and frequent collaborators, socialized together during the early 2000s. Their gatherings included high-profile events like Combs’ White Parties and charity functions. Below is a timeline of their interactions based on available records.

Timeline of Key Events

Early 2003: Kutcher, Combs, and Foxx, already friends through Hollywood circles, socialize frequently. Masterson and Valderrama, Kutcher’s That ’70s Show co-stars, join them at events, including parties at Combs’ Los Angeles home. In 2003, Kutcher and Valderrama attended a Christmas fundraiser at the Scientology Celebrity Centre, where Masterson, a Scientologist, is involved.

2004–2006: The group’s social circle gains attention, with Combs hosting White Parties attended by celebrities like Jay-Z and Mariah Carey. Kutcher, Foxx, Masterson, and Valderrama are seen together at various Hollywood events. Kutcher credits Combs for cultural insights during their collaboration on the 2005 film Guess Who.

2007–2010: As That ’70s Show ends, the group’s interactions decrease. Kutcher focuses on producing and marries Demi Moore. Combs faces a 2007 assault allegation, which is settled out of court. The friends still connect occasionally, with Kutcher and Combs promoting Twitter’s growth in 2009, and Combs praising Kutcher in Time’s 2010 Most Influential list.

2011–2016: The group drifts apart professionally. Kutcher stars in Two and a Half Men, Foxx earns acclaim for Django Unchained, and Valderrama appears in From Dusk Till Dawn. Combs focuses on his business ventures, while Masterson’s career continues with The Ranch, co-starring Kutcher. The friends reunite sporadically, including at a 2014 Combs event.

2017–2020: Masterson’s 2017 rape investigation shifts group dynamics. Kutcher and Valderrama limit public association with him. Combs faces separate lawsuits, including a 2018 claim from a former employee, which is resolved privately. Foxx focuses on his career, avoiding controversy.

2021–2023: Masterson’s 2023 conviction and sentencing strain ties further. Kutcher and Kunis’ letters for Masterson prompt public criticism, and they step back from public statements. Combs faces lawsuits from former partners, including Cassie Ventura, and is photographed with Kutcher at a 2023 charity event.

2024–May 2025: Combs’ March 2024 home raids and September 2024 arrest mark a significant legal escalation. Kutcher, Foxx, and Valderrama make no public statements about Combs. Masterson, in prison, files a 2024 appeal, citing trial errors. The group’s social connections from the early 2000s are no longer active.

Current State

As of May 2025, Combs awaits trial, with no public support from Kutcher, Foxx, or Valderrama. Kutcher continues his work with his nonprofit Thorn and other projects. Foxx promotes new films, Valderrama stars in NCIS, and Masterson’s appeal is ongoing. The friendships that once connected these individuals, prominent in the early 2000s, have largely dissolved amid personal and legal developments.

Sources

This article draws from verified public records, including court documents, news reports (e.g., New York Times, 2003), and interviews (e.g., Kutcher’s 2019 Hot Ones appearance).