What really happened to Drama from Entourage

HBO series Entourage focused on actor Vincent Chase (Adrian Grenier) with glimpses at his inner circle, but his brother, Johnny “Drama” Chase, stole the show plenty of times throughout the years. The irony is Johnny Drama’s real-life counterpart, Kevin Dillon, knows a thing or two about being an actor who has an arguably more famous brother. After all, his brother is Matt Dillon. 

Despite being the lesser-known Dillon (no offense, Kev!) he has scored consistent work since Entourage ended in 2011. He played Bert Lansing on the series How to Be a Gentleman from 2011 to 2012, and he voiced a couple of different characters on the animated series, TripTank, from 2015 to 2016. In 2017 and 2018, he played Jimmy O’Shea on Blue Bloods and starred in the 2018 movie, Dirt. Dillon also appeared in the 2019 movie, Buddy Games.

As for Dillon’s latest gig? In March 2020, Deadline reported that Dillon and Busta Rhymes are going to star as detectives in a thriller called Red Money, which was supposed to begin production in June 2020 in New York City. As of this writing, it doesn’t appear that the movie has started shooting yet, perhaps due to concerns related to the coronavirus pandemic. 

Although Dillon’s been busy professionally, his personal life post-Entourage made some headlines because of his messy divorce from Jane Stuart in 2019. Interestingly enough, Entourage was mentioned in some of those legal documents. Want to know more? Keep reading to find out the messy details and what else Dillon has been up to post-show.

Kevin Dillon's divorce was messy and expensive

Kevin Dillon’s ex, Jane Stuart, noted their separation date as May 29, 2016, just 10 years after their 2006 wedding, according to court docs obtained by TMZ. However, Dillon — who shares daughter Ava Dillon with Stuart — claimed the marriage ended on Oct. 10, 2008. That’s a notable lapse in time, which just so happens to include some presumably hefty Entourage paychecks. 

To clarify the situation, Stuart admitted she did move out of their family home in 2008. However, she said they remained intimate and continued to have meals and attend events together. Stuart even claimed that she and Dillon talked about having more kids in 2015. Hmm.

In March 2018, it appeared Dillon moved on, posting about celebrating his second anniversary with girlfriend Shannon Lewis. At this point, it is unclear if he and Lewis are still together, but their most recent photo together was posted in October 2019. Since then, Lewis gave a March 2020 shoutout to his daughter from a previous relationship, Amy Dillon, for giving her a face mask. 

In June 2019, The Blast reported that Stuart accused Dillon of “making more money than he admitted,” even though he insisted he was making significantly less per month since Entourage had ended. At that point, the judge ordered Dillon to pay his ex $1 million. In November 2019, TMZ confirmed that Dillon and Stuart’s divorce was finally official after years of public disagreements, with the pair sharing legal and physical custody of Ava. Dillon also pays spousal and child support.

Kevin Dillon is still close with the 'Entourage' crew

In December 2017, Kevin Dillon defended his former Entourage co-star Jeremy Piven in response to claims that Piven had sexually assaulted Arianne Bellamar on the show’s set. Kevin told TMZ, “I’ve never seen him do anything like that,” and he described Piven as “nothing but a gentleman.” In response, Bellamar told TMZ that the Entourage set “had a culture of sexual harassment” and claimed that Dillon had made “lewd comments.”

In addition to speaking out on Piven’s behalf, Dillon continually makes efforts to spend time with his fellow Entourage alums in person, posting a photo with Kevin Connolly, Adrian Grenier, and Emmanuelle Chriqui in November 2019. In June 2020, he began hosting Victory The Podcast with Entourage creator, Doug Ellin. The podcast, whose title takes inspiration from an iconic Johnny Drama moment, recaps Entourage episodes with additional commentary. Connolly produces the podcast, and he pops in from time to time with his takes. Although there is much more to Dillon than playing Johnny Drama on Entourage, it’s clear he has embraced the fandom’s love for the character throughout the years. 

Now that we’ve caught up with “Drama,” let’s find out what “E” has been up to since Entourage ended.

If you or someone you know has been the victim of sexual assault, you can call the National Sexual Assault Hotline at 1-800-656-HOPE (4673) or visit RAINN.org for additional resources.

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