Today on the show, I'm joined by Dane Cook to talk about the new documentary about his life and career, Funny Money: The Dane Cook Story. Directed by Brett Harvey hits digital platforms on September 29th.
Back in the mid-2000s, Dane Cook wasn't just big, he was everywhere. He was filling arenas, breaking records, and completely altering the footprint of modern stand-up comedy. But right at the peak of all that, everything blew up behind the scenes. The person he trusted most stole millions of dollars from him, turning his world upside down and kicking off a years-long nightmare. The doc dives into all of it: the insane rise, the brutal family betrayal, and what it actually takes to survive that level of chaos when the dust settles. It's a wildly honest look at fame, money, and the darker side of trust.
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Alright, let's get into it. Here is my conversation with Dane Cook.
Dane Cook: ...this is like the one little area of my life where I get to keep all the crazy shit in my imagination. I'm a grown-up outside of this room, I promise.
Host: I swear it's the exact same thing. It's all contained in this room—all the records, the toys, and all that kind of stuff, it all lives in here. So, the rest of the house: normal 50-year-old adult house, I can...
Dane Cook: We might have to part two this conversation just to talk about the cool shit that we have behind us, and I mean that.
Host: I have questions, but yeah, I want to get into your film.
Producer: We're recording. Go ahead, Tim.
Host: Yeah, yeah, yeah. We're good to go. So, the film. It does this beautiful combination of a true crime story and a comedy. And that's something I don't know that I've ever seen before, and I was so excited for it. I expected it to be kind of one or the other, but not to really toe the line between them. And you slowly build up to the true crime element, and there's this wonderful moment where you call it out, and you're like, "You know this shit's fascinating, right?" because you're like eating popcorn watching your own life to some degree.
Dane Cook: I do say that in there, yeah.
Host: And it's just a perfect reflection of the film, because as an audience, you're kind of giving us a voice to—we're given permission to enjoy the story as it's going on, if that makes sense.
Dane Cook: That's right! Oh man. Okay, so first of all, you know, you have to realize this is my first day today that I'm sort of like really getting an assessment. And when I—when it happened to me, in the first notion—and I'll go into it a little deeper, but just speed-dating it—when it happened toAssertion, and then many years later, after therapy and sort of rebuilding myself, and then even up until like making the doc, all I ever thought from the moment I heard that first answering machine message that my brother left me that I was like, "I have to save this." And I knew I had to save it because I knew it was entertaining. Even in my heartbreak. I swear to you, even though I was literally falling apart at the seams when I heard that message three days after he was on the run, it was like I was like, "My life is already so funny and so interesting because I did this thing," that all I could ever hope is someday somebody would say to me, "That was like true crime and entertaining or funny."
And so, thank you for that. I'm glad that—I'm glad that—I wouldn't have been able to do it. Brett Harvey did that, our director. He blew me away with his work before he even signed on, and once I saw the finished product, I was like, I hope that people receive this the way I'm feeling it, because that's—that moment where I go, "It's kind of exciting," like when he put that in there, and I saw, it gave me permission to actually revel in it a little bit more. Like where I was like, "Wait, shit, I'm okay! I'm okay! We can—this can be that. This can both be like, what the fuck, and still like, that's Dane! I'm—I'm..." And so, the fact that you're acknowledging that really means a lot to me. Thank you.
Host: Well, it's—I think you'll probably as you go through this find out that the story is a little bit more approachable and universal than you might anticipate, where we often have relatives who have fucked up financial things that impact our lives. You know, when my dad passed, there was a lot of financial stuff that had to be sorted out, that we started finding out a lot of truths about him that maybe we didn't fully understand before. And so those things happen, and it's something that I think that there's actually a common moral lesson at this film, in this film, that you can—this sort of financial responsibility that we have to own, and how it impacts and creates a wake around all those people that we love. And it's just—it's a very approachable film, and very relatable, which I was not anticipating because you and I, not a lot in common, but actually when you boil it down, there were—there were actually some pretty common threads there.
Dane Cook: Oh man, that—beautiful, thank you. I think that I have had a lot of conversations with people even just by way of the trailer. And, you know, DMs and now the luxury of voice texts and people can—we can correspond in, you know, more meaningful ways at a distance. But it's like, for me, being able to share this and then receiving not only stories where people say, "This thing happened to me and I don't really know how to get past it or get through it, or I'm still dealing with it," but—but—but the additional element of a couple of people have written me who are—who are the doers of it. Who are the people that that reached out and said, "I got—I found myself in a situation where I put my family through..." And I'm like, I did not expect that people would find this could be somewhat of a hub, my story, to where they want to also confess, in a sense.
So that's new and unusual. But getting back to like the sharing of it and sort of the compassionate empathy that I realized, it was like people are already saying to me like it makes me want to share the thing that happened to me. And I'm writing them back and I'm saying, "I'm—I'm the living example—and I don't know—I don't know if the documentary's going to be a success, but it feels like it, right? I don't know what's going to happen in terms of like what numbers mean and what you know, once it's out of my hands. But I know how I feel today, and I know how I feel just the trailer being out there, and I'm saying to people, imagine taking that worst moment of your life, like I have, and putting it on display, and then potentially like walking into a room with it where it's like the movie 48 Hrs., but you're partnered up with the worst fucking partner ever, because it's the harbinger of of failure, and and an end.
That's who I walk into the room with, and I'm telling other people, if you can do that, you're preparing yourself for a a a beautiful conversation that's being had, because there's nothing to hide. And and by the way, it allows you—it gives you the power to ask questions, because now people know like, "Oh, you're not coming from a bad place, because you're showing me your shit. You're showing—you're showing me your the weakest thing that's—so I know when you ask me the question, you're not trying to coerce me, because you're showing me like, you know, hey, you know my thing." And so for that, very grateful. I'll be able to now entertain people and have an even more of a through line, and a speed-dating, I guess, version of how people know me and how I get to know people.
Host: Well, it's—the thing that's really incredible about this, you're talking about the vulnerability of it, of showing your worst moment and living in this for a couple hours, and everybody has this insight to it. But that's how we move through things. You know, when we have tragedy in our lives, we—at least for me—I've never been to a funeral for somebody that I deeply cared about that I didn't laugh at some point during it. You know, we find comedy in those darkest moments. You can—you see the absurdity in life, it's just part of how we deal with things. And to open yourself up like that, it's got to be cathartic. And I'm just wondering if this is more vulnerable and scary than going on stage, or going on SNL, or that kind of vulnerability, or is this just more raw than that?
Dane Cook: Um, you know, the stage has always been a place where I feel complete. The stage was always a place that made me feel fortified. It's kind of weird. Maybe a longer story for another day, but like, from day one, the moment I got up there, I was more—I was more scared of who I was and I was afraid of the world offstage, but onstage I always felt like a sense of purpose, even if it was not a set that was necessarily good, it was like, "I'm up here. I'm doing this."
And so, no, you know, SNL, yeah, the jitters, and like when you're backstage waiting for Don Pardo to say, "Ladies and gentlemen, Dane Cook!" Um, yeah, you're—you're sort of like, "Ooh, here we go." But nothing prepared me for sort of like the rattling in my chest as I approached the chair for Brett, the director, every day and sat down and really realized like, I'm—there's a camera, and people are going to see this in some capacity, someday. Like, phew. They're going to see me in a way that I'm not prepared necessarily to see me. I'm prepared to share. Um, and I hope that's okay. I actually, to be very honest, I was like sort of scared of that, like, I hope it's okay that people see me this vulnerable, because you've seen me like, I'm the guy at the—and I'm pointing at the rat, like, that's all I ever wanted to be seen as.
And then I understood later like, "Oh no, wait, I do want to be seen in other ways because I want to tell other kinds of stories." So, uh, you know, happenstance, and, um, the way things sort of just like happen in sort of in that Kismet kind of magical way, you know, brought me to sitting there and being like, "Oh my goodness, now I'm going to like show people a a side of this life that, you know, I wouldn't change it now because of where I am, but when it happened, and who I was for the few years after it, was like, um—like humil—the humiliation was, I used to walk through an airport and people would say, "I love your stuff," and now people would say, "I'm sorry."
(Laughter)
Dane Cook: Oof, like, ugh. And it was—it wasn't—there was no next movie coming out, I was not like on the—on top. I was already like past what that first—you know what I mean? I was—I was just—I was a regular human being again, and that was okay with me. I was ready to build the the better rocket. But no, the rocket parts weren't there, the industry sort of like was like, "Yeah, been there, done that." Uh, I didn't know me, I didn't know how to communicate the pain, and I think that even like the plot was lost on me because I had fans, but I had a lot of polarizing people that sort of pulled the narrative over here as well. So dude, like for a number of reasons, there I was finally, you know, before the doc even started, uh, soul searching and being like, "Yeah, really, what am I—what am I putting into the arts? What do I have to offer and share that, um, can move people and move the needle just for my my business, my—to get me back to work to where it's like, 'Oh, that's the story that we needed to hear. It just reminds us that you're a regular person and not just this or that.'" So, you know, here we are, and I'm having the time of my life sitting here talking about the worst time of my life.
Host: Well, I know where we're at time right now, but I just got to say, I—I went by way too quick, I could talk to you about this for hours, but I just wanted to say, I—I heard the story about the stalker, now pairing that with this together, I really hope that you don't have to go through this shit for your next story, because I love the storyteller that you're growing into, um, but I don't—I don't wish that on you, you've had enough, so let's just—hopefully the next story...
Dane Cook: Thanks, man. Thank you, I have great—I have great people, great people around me, great life, great wife, and and new collaborators that feel like they're there for the right reasons. Uh, so for all those—all those reasons, I, you know, I hope that we're talking next time about, I don't know, memorabilia or something else that's out in the world that's entertaining people.
Host: 100%, I hope that's where we are, man. Very cool, and hey, Dane, congrats on the film, man, it's a hell of a show, so great job, man.
Dane Cook: Thank you so much, appreciate it. Thank you very, very much, appreciate your time.
Host: Thank you, thanks guys. All right, bye-bye.
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