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Some podcast episodes hit differently once you know what came after. Join us as we look at podcast episodes that became heartbreaking, haunting, or deeply unsettling due to tragic events that unfolded after their release. Our list includes conversations featuring Robin Williams, Kobe Bryant, Harris Wittels, and more. Which of these episodes affected you most? Let us know in the comments!
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00:00You know what's funny? I wound up, so before Gigi got into basketball, I hardly watched it.
00:05Welcome to WatchMojo, and today we're looking at podcast episodes that,
00:08due to events that occurred after their initial release, are difficult to listen to.
00:12You know, in Nick's case, I think both his mother and I overreacted the first time when we heard of,
00:19you know, the problems, and I think we just way, way overreacted.
00:24Duncan Trussell Family Hour, episode My Mom.
00:26What's it like having me as a son?
00:34It is a joy having you as a son.
00:36For comedian and podcaster Duncan Trussell, this episode is a raw, beautiful,
00:40and now incredibly bittersweet testament to a foundational bond.
00:43Recorded with his mother, Deneen, this conversation is less an interview
00:46and more an intimate, meandering journey through their shared life, spirituality,
00:50and the tender complexities of their connection.
00:52The reason I look better now than I ever have is because I am more fully living.
00:58Right.
00:59Because I'm living and dying, consciously.
01:03Simultaneously, I'm holding both.
01:05They speak with an open-hearted vulnerability that's both disarmingly funny and deeply profound,
01:09discussing everything from their family dynamics to cosmic philosophies.
01:13What makes this particular episode so gut-wrenching on repeat listening is the tragic knowledge that Deneen passed away from
01:19cancer in 2013.
01:20In 2020, Trussell repurposed the audio for the Netflix series, The Midnight Gospel, breaking listeners' hearts all over again.
01:27I have no idea what lies on the other side of physical death, but that there is so much aliveness
01:35that's building in me
01:36that I can't help but think there is some connection between that and the movement toward physical death.
01:44Dopey. Episode Dopey 100.
01:46It is the 100th episode of Dopey. How do you feel?
01:50Good. I didn't think we'd make it.
01:52You look horrible, and you act even worse.
01:55You should hear him.
01:56Um, Dave, if you move your head when we record this...
02:01Do you know how bad our show has been? Do you think it matters if I'm over here, over here?
02:06Dopey was created by Dave Manheim and Chris O'Connor, two friends in recovery who told darkly funny stories about
02:12substance use disorder
02:13and the chaos of their past lives.
02:15The tone was often irreverent.
02:16They intentionally avoided preachy recovery talk and focused on absurd, sometimes horrifying stories.
02:21You know what I'll be?
02:22I'll be probably dead.
02:25No.
02:25You think you'll be a doctor.
02:27I'll be a licensed clinical psychologist.
02:29You could be in the street.
02:31Ugh.
02:32You know, we got some message this morning.
02:34You could be dead. You know, like, statistics say I'd probably be dead, right?
02:38Yeah.
02:39During episode 100, the two joked about how the podcast might eventually end.
02:42At one point, Chris speculated that one of them might get injured, receive painkillers, relapse, and derail the show.
02:47Not long after that episode, he relapsed and died in July 2018.
02:51When listeners later revisited episode 100, Chris's tossed-off joke sounded almost prophetic.
02:57You know what? If one of us ever gets injured,
02:59and we have to take pain meds, like, we have to.
03:02To be accountable, we should only take our pain meds while we record Dopey.
03:07We wouldn't need to take them, then.
03:09You'll never believe this, but episode Octopus Hat.
03:12I had to sleep on the couch the other night because my back was really sore,
03:14and Kipper woke up and found a golf ball of Chris's, because Chris loves a golf ball.
03:19Right.
03:20He loves golf.
03:21Not just a ball.
03:22He just loves a golf ball.
03:24And he's got eight arms, which is...
03:27Amidst laughter and light banter, this podcast's final episode features a moment that, in retrospect,
03:33sends a chilling ripple through the listener.
03:35Co-host Cal Wilson offhandedly mentions dealing with a sore back and sleeping on the couch.
03:39At the time, it was an innocuous detail, a relatable complaint woven into casual conversation.
03:44Things happened fast towards the end.
03:46The meeting room at ICU turned into a green room, and we were all celebrating Cal.
03:52Adam Hills paid tribute to one of life's best people, saying Wilson made everyone happy, offstage and on.
04:00However, the profound tragedy that now overshadows this otherwise delightful episode
04:04is the shocking news of Cal Wilson's sudden and unexpected death in October 2023.
04:08Just weeks after this episode aired, she passed away from an aggressive form of cancer,
04:13the very existence of which was unknown to her and her loved ones during the podcast's recording.
04:18Cal Wilson leaves behind her husband Chris, son Digby, and a legacy of laughter and generosity.
04:25You made it weird with Pete Holmes.
04:27Episode Harris Whittles returns.
04:29Well, what's interesting is, so...
04:33I don't think you know that I went to rehab again.
04:35Here, host Pete Holmes speaks with writer and comedian Harris Whittles,
04:39known for his work on Parks and Recreation.
04:41Whittles talks candidly about his long struggle with substance use disorder and his attempts at recovery.
04:46He reflects on cycles of relapse, the shame that came with concealing his affliction,
04:50and the exhausting effort required to stay sober.
04:53I don't know what words to say.
04:55It's... I mean, it's not a huge deal, but...
05:01Um...
05:02Yeah, it's still fresh. Like, I still haven't figured it all out.
05:06I'm not, like, this guy that's like, sobriety's awesome and...
05:09Despite the heavy subject matter, the conversation also contains Whittles' trademark humor and honesty,
05:14giving the episode an unusually raw confessional tone.
05:17What makes the episode particularly difficult to revisit is what happened afterward.
05:21In February 2015, Whittles died of an overdose at age 30.
05:24In hindsight, the interview feels like a stark snapshot of someone fighting a battle he understood all too well.
05:29And then I proceeded to do it, uh, too much, and...
05:34Borderline over-deed. Over-over-dosed.
05:36Over-deed.
05:38I think I overdosed.
05:39You owe-dosed.
05:40All the smoke with Matt Barnes and Steven Jackson.
05:43Episode, Kobe Bryant breaks down 2010 No Flinch, Shaq Fallout, and Michael Jordan.
05:47Kobe, we appreciate you, man.
05:49What's up, man?
05:49Thank you for your time. Uh, we've been looking forward to this, man.
05:52The fans have been asking, you need to get Kobe, you need to get Kobe.
05:55So we finally got Kobe, man.
05:56Alright.
05:57We appreciate you, man.
05:58You got it, man.
05:58So let's get into it, man.
06:00What is the difference between Kobe Bryant post-career and the Mamba, the killer we saw on the court?
06:07On January 26th, 2020, NBA legend Kobe Bryant, 41, was killed in a helicopter crash in Calabasas, California,
06:14along with his 13-year-old daughter Gianna and seven others while traveling to a youth basketball tournament.
06:19The sudden tragedy shocked the sports world.
06:21In the weeks before the crash, Bryant had appeared on the podcast All the Smoke where he reflected on life
06:26after the NBA.
06:27The novel writing really started just with the kids.
06:30The kids can't keep reading stories that have no relation to them whatsoever.
06:34And I don't mean just from, like, you know, diversity, like a color standpoint.
06:38Not only just that, but from the fact that they're athletes and there's no story that kind of speaks to
06:43athletes.
06:43Recorded just two weeks earlier, the interview finds him discussing his transition from superstar athlete to storyteller, entrepreneur, and mentor.
06:50Most poignant are the moments when Bryant speaks proudly about coaching Gianna's youth basketball team.
06:55The knowledge that both father and daughter would soon lose their lives in the same accident makes the conversation especially
07:01difficult to hear.
07:02Well, coaching the kids is fun.
07:03It just kind of came out of nowhere because my daughter just decided she wanted to play about two and
07:07a half years ago.
07:08You know, so I started coaching a little bit and then she made a local all-star team.
07:15And that's where we met the rest of the girls that are now on the team.
07:18And, you know, they all started at the real kind of ground level.
07:21But they enjoy playing so much, it just kind of grew into what it is now.
07:25WTF with Mark Maron.
07:27Episode, Robin Williams.
07:28When, before you had the heart problem, I mean, you don't seem to be someone who's, like, morbidly fascinated or
07:35hung up on death.
07:37No, I mean, that's weird.
07:38I mean, when I was drinking, there was only one time, even for a moment, where I thought, oh, f***
07:43life.
07:44And then I went like, then even my conscious brain went, did you honestly just say f*** life?
07:50Comedian Mark Maron's WTF was renowned for its ability to excavate the innermost workings of his guests,
07:55often revealing vulnerabilities and struggles beneath the public persona.
07:59His interview with the legendary Robin Williams is no exception.
08:02A conversation that, in retrospect, becomes agonizingly poignant.
08:06Can I ask you what you're doing right now?
08:07You're sitting naked in a hotel room with a bottle of Jack Daniels?
08:11Yes.
08:12Is this maybe influencing your decision?
08:14Possibly.
08:15Okay, we're going to put that over here and tomorrow morning.
08:17And who's that in the bed there?
08:18I don't know.
08:19Okay, well, don't discuss this with her because she may tweet it.
08:23Okay, this may not be good.
08:25The tragic layer is, of course, the knowledge that Williams took his own life a few short years after this
08:30interview.
08:30Knowing about the profound depression and battle with Lewy body dementia he was secretly enduring
08:35transforms the interview into a haunting, almost unbearable portrait of a man grappling with unseen demons.
08:41Okay, so have you ever thought about it since then?
08:45No.
08:46During the surgery, were you thinking about death?
08:49No.
08:50Why?
08:51Because you just were thinking everything's going to be fine.
08:53Man, was that your mother talking?
08:54Maybe.
08:55She was a Christian scientist who had plastic surgery.
08:58Wow.
08:59Is that a mixed message?
09:00Yeah, that is.
09:01Inside Out with Paul Mercurio.
09:03Episode Rob Reiner and Nick Reiner.
09:05You said you both learned what you were going through in a deeper way.
09:09Oh, he's right here.
09:10You can ask him.
09:11No, that's your son.
09:12You can ask him.
09:12That's Nick.
09:12Wow, I guess I should have known that at the beginning.
09:15Come in here.
09:15Come in here, man.
09:16He wants to know what you took away.
09:18Here, I'm going to get you one of these.
09:19Yeah, yeah.
09:21Nice to meet you.
09:22This podcast once featured a deeply personal 2015 conversation between filmmaker Rob Reiner
09:27and his son Nick, who spoke candidly about his struggles with substance use, treatment,
09:31and the ongoing challenge of staying sober.
09:33When he was saying before, like, how I was scared to get in trouble if I were to tell them
09:38the truth, because they always say, be honest, be honest, be honest, and that's the best
09:41policy.
09:42But it's kind of not the best policy when you're honest and you get in more trouble than you
09:46were if you were lying.
09:47That's exactly what my son said.
09:48The episode has since taken on a far darker resonance.
09:51In December 2025, Rob and his wife, Michelle Singer Reiner, were found fatally stabbed in
09:55their Brentwood home.
09:56Nick was arrested hours later and charged with two counts of first-degree murder.
10:00He has pleaded not guilty.
10:01Reports also noted that he had previously been prescribed medication for schizophrenia.
10:05What was once a hopeful conversation about recovery now stands as a tragic and unsettling
10:10record in light of the events that followed.
10:12Did you feel guilt?
10:13I don't know if somebody at that age feels guilt.
10:15Did you feel guilt?
10:15I did honestly feel guilt.
10:17I'm not just saying that for sympathy points, but I, you know, you feel bad when you lie
10:20to your parents.
10:21Yeah.
10:21But it's designed for you to lie, I guess you could say.
10:24If you or someone you know is struggling with mental illness or substance use disorder,
10:29please don't hesitate to call the Substance Use and Mental Health Services Administration
10:33hotline at 1-800-662-4357.
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