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Jon Cryer on ‘Serial’ Obsession, Why He Supports Adnan Syed

Actor hosts weekly “Addendum” episodes for second season of true-crime podcast ‘Undisclosed.’

Jon Cryeron is hosting weekly "Addendum" episodes of the second season of 'Undisclosed' podcast.

Jon Cryer is probably best known for his comedic, scene-stealing role as Ducky – the pompadoured best friend Molly Ringwald should have taken to prom in Pretty In Pink – or for his lucrative, 12-year turn as Alan Harper on the astronomically popular CBS sitcom Two and a Half Men. But earlier this month, the Duckman took on a new role when he was tapped to host the weekly “Addendum” episodes of the second season of the true-crime podcast Undisclosed.

If you’re scratching your head over what appears to be a pretty random career choice for such a successful Hollywood star, don’t worry, you’re not alone. Cryer’s interest in criminal justice issues will likely come as surprise to anyone who doesn’t follow him on Twitter. That’s where Cryer has spent the last year-and-a-half tweeting his support for Serial subject Adnan Syed, who recently had his conviction for first-degree murder overturned. After the podcast ended, his continued interest in the case led him to be an early fan of Undisclosed‘s first season, which excavated the investigation that led to Syed’s arrest in painstaking detail. Cryer’s public support for both Syed and the podcast led to some chummy tweets with Undisclosed hosts Rabia Chaudry, Susan Simpon and Colin Miller, but even he was “mystified” when they approached him about hosting the weekly bonus episodes.

Focused on a whole new case – the conviction of Joey Watkins for the 2000 murder of Isaac Dawkins in Rome, Georgia – the second season kicked off on July 11th, and a new episode is released every Monday. Cryer’s “Addendum” segments – in which he and his guests discuss the Watkins’ case and the broader legal issues – drop every Thursday. Rolling Stone spoke to Cryer about his interest in criminal justice issues, what podcasts offer that traditional journalism does not and how he’ll continue to listen to Undisclosed every week just like any other fan.

A lot of people maybe don’t realize that you’ve been an adamant supporter of Adnan Syed’s. How did that come about?
I’ve always been curious about the criminal justice system and enjoyed a lot of true crime writing. I’m fascinated with how we perceive criminals and the notion of “justice.” The thing that attracted me to Adnan Syed’s case was, of course, Serial – my wife and I used to hunker down in bed every week and each take an earbud and listen to the podcast together. It was great, like a radio show from the 1940s. As a piece of entertainment, Serial was a beautifully produced story, but these aren’t characters – these are real human beings. I’ve served on a couple of juries and I always found that the entertainment industry, in portraying the criminal justice system, did a horrible disservice, because people come into jury rooms with their heads full of mythology. And the reality is so not like what you see in entertainment. Obviously, Serial portrayed Adnan’s case as story, but the reality was much more complicated. 

Undisclosed was willing to go into much greater detail and depth over what was a very complex situation. This is a fascinating new era in journalism. Podcasts offer a way for people to make huge amounts of information about a case available to the public – all the documents associated with a case could be put online concurrently with the discussion. You end up spending 22 hours going through all these details that no journalist could have ever provided for you before.

How did you end up being tapped to host the weekly Addendum episodes of Undisclosed‘s second season?
There’s another podcast called Truth & Justice hosted by a guy named Bob Ruff, who is a former arson investigator. As a hobby, he started looking into Adnan Syed’s case and podcasting about it, and has since done an absolutely remarkable job of investigation not just in that case, but in three other cases down in Tyler, Texas. I enjoyed his podcast, so I contacted him over Twitter, and then he and I started emailing about various theories we had about Adnan’s case. Then I started having Twitter interactions with Rabia Chaudry, Colin Miller and Susan Simpson [who featured some of Ruff’s findings during Undisclosed‘s first season]. I’m just a fan! I think they really do a remarkable job – even though they’re clearly advocates for Adnan, they took great pains to be fair with the information. 

One day, I got a DM from Susan Simpson sending this silly graphic, which said “Hey Ducky, would you be our Chris Hardwick?” It was funny because she sent this red Valentine’s heart with a little ribbon on it, but it was surrounded by these odd curlicues of what looked like pubic hair, and I was like, “OK, these are some odd mixed messages.” Anyway, I’m not a lawyer, I just have an avid interest in this stuff, and the Undisclosed team was hoping that I would host a fan interaction show like The Talking Dead is for The Walking Dead

Adnan Syed had his murder conviction vatated after his case was featured on 'Serial' and 'Undisclosed.'

Were you surprised?
I was mystified! Who wants to hear what the guy from Two and a Half Men has to say about the criminal justice system? That said, I’m really interested in these issues and when they asked me, I wasn’t going to say no. They did “Addendum” episodes the first season, but they ended up being regular episodes for all intents and purposes, so this time around, they wanted to use these episodes to give listeners a way to interact with the case and ask questions, as well as have discussions about the broader issues with some really interesting guests.

I mean, they gave me the opportunity to ask a sitting Congressman [Keith Ellison, D-Minnesota], “How come we can’t federally mandate police de-escalation classes?” I’m not going to refuse that offer!

Did they give you the full debrief on Joey Watkins and the murder of Isaac Dawkins?
Actually, I didn’t know anything about the Joey Watkins case going into it – they asked me whether I wanted to be filled in, but I said, “No, I want to discover it as you guys present it.” All they sent me was a link to an article about his conviction, which contained just the basic facts: that he was convicted of Dawkins’ murder; that the victim was found shot in his truck on the side of the road; and Watkins’ family was insisting that he was not guilty and his conviction was a travesty. That’s all I know about it.

Like the listeners, I don’t know if this guy is wrongfully convicted or not, but I look forward to learning more. It’s fascinating to be a part of how people are going to get information on this case. I think we so misunderstand the criminal justice system as it currently functions. Rabin, Colin and Susan are all attorneys, and Rabia has been fighting for Adnan for quite awhile – everybody is aware that this is a system that is screwed up, but it aspires to be better. I think they all have real hope that these issues will be addressed and repaired. It’s going to be one at a time, in increments – it’s not going to be a sweeping revolution that changes everything overnight, but the hope is to chip away at the justice system’s failings.

You’re probably going to learn a lot by hosting and participating in these conversations, too.
Yes! And I’m also learning how to be an interviewer! The first time I did it [for a special episode of Undisclosed about Syed’s vacated conviction], I was petrified. I realized I didn’t know how to interview people! I sounded like I was having an aneurysm. But I was also overcome with the enormity of the moment, of Adnan’s conviction being overturned. It’s been such an emotional journey for Rabia, and obviously Susan and Colin as well. But yeah, I’m still learning how to be a podcaster!

You’re being paid a fee to host “Addendum” — which you’ve said you plan to donate?
Yeah. I’m going to use it as a way to publicize different organizations who are working on behalf of people who may be wrongfully convicted. [The first organization Cryer donated to is the Jeffrey Deskovic Foundation for Justice, which was started by an exoneree who spent 16 years in prison for a rape and murder he did not commit.] I’m not looking to make money doing this, and you don’t get into podcasting for the money anyway. I’m also cognizant that these are people’s lives – there are real victims and their families who have been really hurt, there are police officers who are really trying to do a good job, there are prosecutors who are doing the best they can. The process is screwed up now, and there are people who do their jobs well and there are people who do their jobs terribly, and people’s lives are hanging in the balance. This seemed like an opportunity to draw attention to some of those organizations that trying to make an impact.

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