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Dane Cook is stand-up comedian and film actor. He’s released five comedy albums, including one of the highest charting comedy releases of all time. He’s been called the “first internet-made stand-up comedy star” who grew a massive fanbase online which slingshot his career to Rockstar status, becoming one of the most prolific and popular comedians of the past few decades, selling out arenas and stadiums, while appearing in a number of movies over that time. He’s also known for his use of observational, storytelling humor with a dynamic on-stage personality. We talked to Dane about his life, his incredible career, some highlights, what he’s doing now, and the following:

  •  Why I Got Into Comedy
  • Inspired By “Fearless” Comedians
  • The Influence Of George Carlin
  • The “First Internet-Made Stand-Up Comedy Star”
  • How To Create A “Fan For Life”
  • The “Slingshot” Moment
  • Rockstar” Status
  • The Power Of “Self-Actualization”
  • The Changes That Come With Success At A Young Age
  • The Importance Of Mentorship
  • The Success Of “Retaliation”
  • How Stand-Up Compares To Acting
  • Hosting SNL
  • Time Is Precious
  • Advice For Young Comedians
  • My Best Work Yet
  • What I Do For Fun
  • Dinner Guests
  • What “Legacy Means To Me

Every week, the RUN GPG Podcast aims to provide inspirational stories from people who made a mark in entrepreneurship, business, entertainment, the arts, personal development, and the real estate industry. It is produced by the GREATER PROPERTY GROUP with the intent to help our audience grow and scale their business and their life.

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Dane Cook is a standup comedian and film actor. He’s released five comedy albs, including one of the highest charting comedy releases of all time. He’s been called the first internet-made standup comedy star who grow a massive fan base online. Which Slingshot his career to rockstar status becoming one of the most prolific and popular comedians of the past few decades, selling out arenas and stadiums while appearing in a number of movies over that time, he’s also known for his use of observational storytelling hor with a dynamic onstage personality.

We’re excited to talk to Dane Cook about his life, his incredible career, some highlights what he is doing now, and a lot more Dane it’s an honor. Welcome to the RUN GPG Podcast. Appreciate it, man. Thank you for having me. Yeah, excited to have you, but, we made it happen, which I’m excited about. You know you are, as I was saying in, the introduction, there you are one of the most iconic comedians of the past few decades.

We can say, you know, my generation, our generation, you know, grew up with your comedy, your albs, your movies. So it’s gonna be good to hear a little bit more about your story and talk about. Your life and as mentioned some career-high highlights, but before we get into the meat of it, I want to unpack your actual comedy career.

If that’s cool. And I wanna briefly set the stage and ask the question. Sure. Who is Dane Cook? Where are you from? Where did you grow up? And maybe tell us what the young, Dane was like. so I was born in Cambridge, Massachusetts, right outside of Boston. Grew up, one town over Arlington, Massachusetts.

And, I was, I was a quiet kid. I was, I was the opposite of the class clown. I was an introvert. I had a lot of social anxiety and, yeah, all the, all the things that, you know, you, I think you need to catapult you into the, very, very stressful world of, of standup comedy. But even though I had a lot of, you know, barriers early on in life, there was always this.

Deep need to create and share those ideas. So I knew from a very early age that when I was in my comfort zone, when I could get away from fear and anxiety, that I was pretty much laser-focused on the skits or the, whatever it was that I was putting together in, in our household. I was gonna create the best show to entertain my family.

So there was a little bit of that early knowledge that I had some showmanship, but I just had to unpack a lot of, BS to get from, you know, doing it in the comfort of my home to a stage somewhere. You, you know, what’s really interesting about that is I I’ve heard you, say that you grew up an introvert and somewhat shy.

‘ve heard you say that. so what made you get into comedy? It’s probably, I, you know, this is where it’s like, I should be laying down it’s like therapy, but it’s that thing of like, you know, comedy is it’s, it’s an escape from, from fear. comedy is a great way to circumvent. Pain that you may feel is coming towards you, whether it’s, through bullying or perceived ideas that you project that other people might feel about you, comedy is a great kind of safe Haven.

It’s an escape, it’s a safe Haven. It’s, it’s armor. so for a lot of those, you know, reasons early in my life, I found that I relied on comedy to probably distract. From stillness and, and, and, and quiet, and the ability to be really present with people. Comedy was a great put on a facade if you may, to, to, to buy me some time with the people that I was with.

So they didn’t see me as how I felt, which was lesser. I, I think we do need that coach. I think we do need that coach to slide down on, but you know, it, it, I I’ve heard creatives say that quite often. Right. It’s, it’s somewhat of an escape. So, at that time you get into comedy and I’ve asked you this before and, and I I’d like to hear it again.

So what comedians were you influenced by the most when you actually got into comedy? Like who did you grow up? Listening to and watching? I mean, there was a lot of standups that I wanted to. But it was the ones that were, what I felt was, fearless. I mean, I learned later in my career that, you know, anybody who gets up on a stage has to have some, some fearlessness, but the ones that really would command a crowd and, and kind of take over, I felt like, they were the bravest people that.

That I had witnessed, usually on television or maybe old comedy albs that I got a hold of. George Carlin certainly was such a great, he was moving the needle throughout my young adult life. He was going through his own, metamorphosis as an artist. And I kind of watched him go from these early ideas of being the hippie dippy weatherman to then kind of killing that, character and letting his true process bleed into the comedy.

But he was still outrageous. He could still do things that were so, you know, not conventional, he could be political and then a minute later he could be doing something really irreverent and. You know, somewhat, even childish. and I loved that. I loved that. He allowed himself to be all of the things that he had experienced in that one hour of, of comedy.

And, and I’m sure we’ll get to it. But later in my life in career, 20 years later, his early work definitely influenced the people that I worked with and how I started creating and in cultivating my brand in presenting it to my audience and hopefully new audiences that were checking. Yeah, it’s crazy.

When you, when you look at George Carlin, like he was, he, he was cerebral too, you know, looking back, he was very, you know, profound in a lot of ways, you know, emotional in some ways. Right. So, now here’s, what’s interesting. you’ve been called the first internet-made standup comedy star. Did you know that people have lived?

I think I think I said it. Yeah. Okay. Well, maybe you okay. You labeled yourself. That’s good. because you’re one of the first comedians to use a personal webpage in my. To build a large fan base, which I find fascinating, really entrepreneurial at the time. In fact, you were described as now, check this out.

You were described as alarmingly, popular alarmingly. Like it shocked people right. Nobody more shocked than me. Yeah. Alarmingly popular during that era. and to this day, people still reference that. Right. So can you tell us how you did that? Like how did you grow your brand and ultimately your career on one of the first social sites ever.

Yeah, it, it was well kind of like going backwards when I was about two years into realizing that social media was at that time, a new portal that wasn’t the, the obvious kind of benign choice today that everybody is, hopped up on and participating in back then, it was still very, it was like there was a new generation that was understanding the internet and logging into.

Various websites. And then there was like a whole lot of people that had no clue really what, the digital realm was or was, was going to, become. But I, I was, I was into it. I was hip to the idea that this, internet age was going to change well, commerce. I realized really quickly because. Even on the early, early versions of my space when I had just maybe 10,000 followers before I hit several, several million, you know, people would say, can I buy your item?

Will you send it to me? And so I’d be a one-man fulfillment center and shipping out and people would like, sometimes just send me, send me the money or send me a check or, you know, like the honor system. But I was making. I was paying the rent. I was paying, you know, for my little, you know, dinky apartment out here in LA by, corresponding with people through the early version of my space.

And then as it built and it grew to several million, it was like, oh, I’m, I’m writing my own. My own narrative. I’m, I’m punching my own ticket and I’m not waiting for the industry or somebody else to say, you know, you are next. I was putting myself on the map and when I kind of half joking, half truthfully say, yeah, I was the one to break through and do that.

I was, I was realizing in real time, nobody’s doing this. I’m not even hiding it. I’m I’m sharing the, the, the blueprint I’m telling other comics I’m going on. Morning radio. I’m. This is how you’re going to become whatever you are meant to be without waiting for the, the machine to pick you up. So, yeah, it was like, I was the first one to the, the finish line in a lot of ways.

And to this very day, it, it influences how I correspond, how I choose to kind of take that narrative. And where do I wanna go with it next? And how do I wanna evolve 30 plus years into standup comedy? And it was from those early, You know, trials and tribulations with social media. Yeah. It, I, I think it’s a case study in that, you know, like to this day, people talk about Y you know, replying to fans responding, being approachable, consistent.

That was something you did. I think that moved the needle probably on your, on your career quite a bit, because you were approachable and you were engaging. That’s what people talk about in social media all the time. Like, how do you engage. One of my tricks was an trick, but one of the realities, that I, I, you know, just realized pretty quickly was because of feeling so isolated as a, as a kid, and now having this popularity and finding ways to interact with people in my comfort zone, because I was home.

A lot of that. It wasn’t like I was at a meet and greet or doing this at a, at a seminar. I was able to very comfortably like we’re chatting now be, be in a place. You know, very present very down to earth and I could be funny, but I could be mindful. I could be a lot of things because I felt a real trust.

Why would anybody be engaging with me through this portal? If they didn’t wanna be here? This is pre-hater side, like haters versus like this was when it was kind of like way more jovial and exciting to, to be a fan of somebody. Fandom was at an all time high and it was less about. People coming in a rabble-rousing and wanting to just, you know, dr up some attention by being the opposing, which is, you know, par for the course.

Now that’s part of the industry as well. If you don’t have opposing and you don’t have naysayers and rubber necks that don’t like, you’re, you’re not doing it right. In a lot of ways in that era, somebody could come in, get to know me and I. Realizing in real time. Oh, it’s about we, this isn’t look what I did.

Look what I’m accomplishing. I, I, I could say those things, but the reality was it was the people that I was finding through here that I would, my, all my updates were about. We, I, everybody that was in that, digital space, I made sure they felt a part of the street team, a part of the producing team. A part of the reason I, I was raising that flag up the banner because it was a we experience.

I think it’s a mistake. A lot of people make, even to this day, they don’t create a we environment. They create a look at me environment. And when you create a look at me environment, somebody’s gonna look, but they may not linger. They may not look too long, but if you create an experience where people feel emboldened and important to your journey, you might have a fan for.

Oh, that’s a mic drop moment. I hope everyone’s paying attention to that. Cause that was some science. that was really smart. Now. I, I, no, I’m serious. That was really good takeaway. Unbelievable. now I know you put the work in, I know this, I know your career. I know you put the work in, but it seemed like.

Almost overnight you blew up. And the next thing you know, you were selling out stadis and arenas. Like what was the pivotal moment that did it for you? Like, can you pinpoint at the moment, the Slingshot that, you know, when the rocket ship happened, can you pinpoint it? Well, it was, I, I wish I could say it was a Slingshot moment because the reality was there was probably about, I mean, forget about the fact that I started in 1990 and I pretty quickly was laying the ground.

In Boston, in new England for, at least regional success. What, what does that mean? Do a great show and hopefully they hire you back in the next, you know, semester and lo low totem pole. I make a living locally doing local standup comedy. Okay. so I was really just patting my, local regional tour map.

And yet the more I was doing these shows and putting my best effort into these shows. People were starting to call me from further away and saying, are you for hire to come to Vermont? Are you for hire to come over the border and come into, you know, somewhere in Canada? And so then I, in the mid nineties adopted this philosophy as I’m not gonna try to go anywhere until I’m invited, I’m gonna stay in one place and I’m gonna grow.

So, good at my craft in that place, that the spillover, the word of. Will allow somebody to travel to another place and go, we should get that guy that I saw back in Boston here. And I did that for New York city. I did that for LA. Some people go too soon. They go to New York too soon. They’re not ready.

They go to LA too soon. They just languish out here. And I try to really enforce in, in young artists or out of comedy, be your best, where you are until it’s under. And once you become undeniable at what you do at a high level locally, people will recognize that and want to bring you to their region, to their platform, to their stages.

It works like that. Right? So I, again, not a, not a, not a singular moment, but just growing locally and then getting some local recognition that, but if I, if, if I had to if I had to honestly pin it, it was probably building, building. And then I did Penn. I happened to be documenting it for an HBO series called togas that I was on and Penn state was supposed to be a 5,000-seat show.

And about two weeks before the show, we got a call from the head of, you know, entertainment, marketing there. And they said, can we move this show to the field house? Because too many people wanna come to the theater. And I said, how big’s the field house? And they were like, like 14,000. I was like, how many more than the 5,000 are we at?

And I think at that point it was like 7,800 when we got to Penn State. And that that episode is on there. You can see, you can see me arriving in my moment in real-time. Cause when I walk on the stage, it was like 12,500 people. And then more people continued to come in during the show. So it was Penn State.

And when I left that stage that night and left that show. I recognized that the wave was at its, you know, largest and I could pretty much take it wherever I wanted to, if I could stay, as enthusiastic I, as I had been. That’s really cool. I, I didn’t know that, as I was saying though, like, you know, you became a rockstar, like you became a rockstar personality, like of my generation anyway, or certain generation.

Right. But I never trashed a hotel. I, I, I don’t believe it. I do not believe that actually, you don’t receive rockstar, status until you trash a hotel room. Now here’s fucked up thing. My mom growing up was, a housekeeper and she also just loved keeping a clean house. So I was probably the only rockstar that cleaned my room for the housekeeper before they came it.

Wow. a respectful rock star. but you, you know, like that’s the way I remember you from, from then when you were doing the, you know, the Madison square garden, like you, you were this bigger, larger than life personality as a comedian. And the question I wanted to ask is, and I talked to creatives and, and, you know, successful people about, you know, manifesting vision, whatever did have you always had a big picture outlook, like, did you know you were gonna become a rock star?

Did you have that? Well, I dunno if. Thought of it as a rockstar, but I, I knew that I was in it for the long haul and I, and I had, I had kind of put it out there and shared with people closest to me. Like I’m not doing this to be kind of funny or go halfway. I’m doing it because I wanna be the best at this for my generation.

And I feel like I, I can and could be that if I’m willing to do the work and evolve and grow, I think if I had to kind of put it under, you know, one. Put it on the screen. It’s about self-actualizing. Yep. And you have, you have to, in your writing, in your meditating, in your prayer, in your process, you have to see and believe yourself.

The only way you can do that is if you remove. Your own so that when your meter is picking up everything else in the outside world, it’s not thrown off by the fact that you’ve got a clean house as well. You have to live in your truth. So if you want self-actualizing to come to fruition, then the catch is you can’t be false.

People will sense it. People will detect it and people might hang around for a little. But the truth is the most alluring thing you can put into anything in this world. And if you put your truth into your art, whether they like you kinda like you love you adore you check in with you. The truth will always be alluring to that person.

And they’ll wanna spend some time you with you from time to time. Authenticity. Trp’s all. now I’ve also heard you say this. I’ve heard you talk about being, a lone Wolf for being isolated in a way, because you hit the stratosphere at 20 years old. Did you feel alone with that happened? And also, can you talk about like maybe, you know, not to get, you know, too, emotional here, but the, the loneliness and hardships that come with like insane success, like you had at a young age?

Well, it’s like, there’s two sides to that. And it’s a tricky question to answer because on one side, yes, it’s very isolating because when you are achieving a pipe dream, people around you. Tend to not know how to communicate certain things, or they think that there there’s a lot of beliefs that people have about the person that’s becoming success.

Oh, you won’t have time for me. I didn’t wanna bother you. I don’t wanna. So for a myriad of reasons, it, it, it can be a, a bit of a lonely journey. On one side, I was prepared for it because I was very good at being alone. I was comfortable at that point in being alone and I had the digital window, so I never.

Really like, desperately alone because I enjoyed my work and my communication with fans through the internet. On the other side, when you’re becoming the bell of the ball, there’s a lot of people that wanna spend time with you. And so there was another entirely new element that nobody gave me the playbook for, which was what is it like to be the.

In that moment, like, you know, what do you have access to? Where do you wanna go? That maybe before you wouldn’t have been invited to, but suddenly every door’s gonna be open to you or there’s certain cool people that you, you like, and now suddenly they’re fans of yours and they’re inviting you into their world.

And so the cross-pollination from reaching a high level is exciting. it’s thrilling and yet it can be a little bit lonely on. Fundamentally down-home basis. Cuz a lot of people are seeing this new version of you that they perceive as a new version. And you kind of have to relearn how to, cohabitate with people.

And a lot of times that’s strictly because of how they perceived you having changed. I don’t feel like I changed a lot. I feel like I was still like a jeans and sneakers guy. I had a couple of things that like I had my eye on that I wanted to, you know, spend a little bit on or, or, you know, Take myself on that shopping spree, but truly I was most enticed by reinvesting back into the work, back into the brand, back into the business of show.

And, and I also, once I had access to that kind of inner circle, then, then it was the quest of how do you stay in, how do you, you know, change your narrative? What is the zeitgeist who’s really in control of what? And. How can you use, continue to use what we’re doing here today to, create your own paths?

You know, whether that’s financially, whether that’s messaging me, whether that’s, therapy, whether that’s, you know, whatever, whatever dynamic that it is that you wanna share here. So it continues to be a fascinating kind of per thrust. The way the industry changes and the way you grow and change in your audience and what do you provide and what do they then get in return that keeps us all wanting to stay on the journey with each other.

Yeah, that’s, that’s incredible. And it’s actually really interesting. You know, you talked about that shy, introverted. You know, kid from Cambridge, right. and then, you know, at 20 years old, you’re, you’re the next Steve Martin, they say, right. So it’s gotta affect your ego at some point. Right. So, or something, you know, it’s gotta affect the way, like you said, you didn’t change, which is really cool, but other people’s perception would change.

Right. So, well, I mean, it does affect the ego. It affects a lot there. There’s certainly a lot of things that, that get kind of triggered. You’re then sometimes, then there’s people that say want access to you and they’re they’re nefarious. You know, they wouldn’t have wanted you when you were a quote, nobody, but they want a piece of you now.

They want to be on your pullout, you know, coattail. They want to be whatever it might be. So you have to then go through the spanking machine of the industry in life because now certain people want you for absolutely the wrong reasons. Some people are wired and programmed to take their takers in this world.

They’re not. Villainous, but sometimes they’re just not thoughtful and mindful people. So you do have to start putting on a more assertive noble mentality, because if you don’t, your boundaries are gonna get trampled. and, and, and when you do that, when you lay those boundaries down and you start becoming the, your own gatekeeper of who really should get caught well, then that can piss.

People that are genuinely there with love and meaning, because now they’re being halted, but it’s part of the process of trust and, and, and letting people, you know, giving people your power and, and so on and so forth. So for all those reasons, yes, you, you. You have to become this other thing to protect yourself, but you still at your core need to get back to the essence of who you are quite simply as a han being and not a performer or not anything else, just a, a kid who grew up and does what they love.

And how do you get back down to. Communicating that message to people. But over that time, did you have a mentor? And if so, did they, like along the way, did you have anybody that helped you with that mentors? Did they help you along the way? What did they teach you? I, I did. I’ve had a few people, man that, you know, really touched my heart and, gently kind of guided me towards a better version of myself.

And I would say more than anybody was my high school drama teacher, Frank Roberts. He sadly passed away some years ago. But that man was the first person outside of my family. That was very honest with me, honest about the world at large, honest about where I was at that point in my abilities to, to entertain people.

He watched me on stage during our class and then in some of the plays that he cast me in. And not only that, but we just created a friendship to where I spent a lot of time during school with him, discussing art, discussing philosophy, discussing, you know, self-actualizing. You. Inwardness all that stuff.

And for, for a lot of reasons, I’m where I am today because of the love and the craft that Frank Roberts had experienced it in his life and then shared with me. Yeah, that’s cool. It’s I important to have, I always like to ask that question of successful people. thank you. Thank you for asking it because I don’t, I get to acknowledge him enough.

So. Frank Roberts. Thank you. Shout out to Frank Roberts.

Over that time you released five comedy albs, including retaliation, which debuted at nber four. On the billboard 200, which was the most successful comedy alb debut. Since Steve Martin’s a wild and crazy guy in 1978, it went gold six days after its initial release and eventually went double platin.

That time I feel like it was the golden age of comedy albs. that’s the way I feel. I, you know, I could be wrong, but what are your thoughts on why your albs were so popular and what does it mean to, to have that distinction is one of the greatest comedy alb releases of all time. It’s it’s amazing.

It’s it’s an honor. It still speaks to the kid inside me that listen to a lot of comedy albs and, and just, you know, imbibed on all things stand up. So it’s exciting to have my name, you know, in those conversations and, and recognized in that way. I think that what, well, first of all, they’re, they’re, they’re funny.

they, they work. They, they, they make people laugh into this. People can put on any of those albs and they have a timelessness, which I wanted at the time. I didn’t do a lot of news of the day stuff. I don’t want really to do too many things that I felt like, cemented it at a time, as opposed to what I thought great storytelling could be, you know, something 20 years from now, or, or whenever that, you know, real han emotion mixed into.

Narrative is, appealing regardless of when somebody listens to it. But I think that if I got down to like the, what I saw was missing, and again, I love talking about kind of the, the, the business PR the talking shop side was the comedy alb was considered dead because the comedy alb was not being given any real care.

They were, cheap. They, they looked cheap, they were packaged cheap. They, there was no art. On the cover. It was like kinda like a silver disc and a jewel case. And, and they were boring. And I, I grew up with big alb vinyl alb covers that made you wanna stare at it. And like, there was a story being told there.

So that was a lot of what I thought helped kind of resuscitate the comedy alb that not only was the content great, but it was something you wanted to have. You wanted to hold onto it. You wanted to read. Liner notes and see what I hid on the alb art. And maybe I drew the, the back of it, like on harmful and I, that was during the edit that I sketched the whole track listing.

And I think the care that I put into the product made it more valuable to people and more people wanted it for that reason. Yeah, it was, it was an interesting time with comedy albs. I, I, I mean, everybody had your, your CD, everybody had it. yeah, it was a fun time, but it was, yeah, but it was also cuz we were coming outta that strange era where in the nineties comedy had, it was so oversaturated and poorly presented from.

Comedy central and some of the other places weren’t giving it the same deep dive cultivation. And it just got a little lazy. I think that it, that the comedy got a little lazy, the era because the nineties was coming off this eighties, boom, where everybody wanted to be a major superstar now because of Roseanne and Robin Williams and Seinfeld.

And it just, it was, what like a glut. It was, it, it just, it was too much all the time with not enough exceptional. Performers being kind of set apart from the Flom and jet some. And so for all those reasons, and, and by the way, it’s gonna happen again. And it always happens with, with every form of entertainment, it just was, it needed a jolt, it needed somebody new, it needed, young, you know, that next generation of people to come in and give it a spin for my generation growing up.

And I think I hit all the right, you know, connected the right dots at that time. Yeah, the ti I think the timing was perfect. you showed up at the right time for a lot of us, besides your insane success as a comedian performer, you have a successful movie career. you, you became an actor, early on, right?

, you did. How did that happen? Like how did you get into acting and how does the experience as an actor to compare, to stand up? Common actor is compared to standup comedy. It’s a, it’s a great question. And it, and it’s very different because standup is such a solo mission and stage or television film is it’s a collaboration.

And also you’re, you’re playing a part for a director’s vision. So for a nber of reasons, I love it equally, but it uses a whole different side of your, abilities. And also comedy is. Real-time. No, take two. I feel like a lot of my early movie career was just based on fans. You know, directors that had grown up with my standup, Kevin Costner saw me do standup comedy at the laugh factory in LA.

So by the time I sent my tape to Kevin, he was a fan of my standup. And then he was his words, you know, he was like, oh, I was impressed that you put. That kind of effort and, and passion that I’ve seen in your standup. He was familiar with my work ethic and when he saw that I shifted it into something that was, you know, more, layered.

He very quickly was like, you got the job let’s, let’s get to work. So a lot of that just came from the, when you hit the zeitgeist and your, the talk of the town, you get a lot of incoming calls. Some of them are interesting and a little weird. And then a few of them are exactly what you wanna put that, that try into next.

I’m surprised you never had a show. Like your guy, like to me, you need, you need your own show. Like, I, I, we try, man. I, that was one of the areas where it’s like, I had a lot of collapsing you know, it, for all the things that we could talk about here is like high watermarks. We, we tried, man. I tried. Two pilots with Sony.

Thanks to the great Russ Krasnoff who was producing over there. He, after the first one, just wasn’t very good. He’s like, let’s give it another try. He brought in another, you know, production team. So Sony and Russ were great. Just didn’t work. NBC and myself. We tried something, I think in hindsight, my standup at that time, which was really.

Performance-based with writing. It was like, it was so it broad that we couldn’t quite figure out how do you shrink that down to TV? And, and, and quite frankly, I look back now and I’m like, I’m glad it didn’t work, or I’m glad it didn’t take because I, I was still not ready and had not grown up enough to be able to really tap into the kinds of stories that I wanna be able to share, which is heart and hor.

At that point, there was a lot of hor and I, I wanted people to know, that other side of me and I wanted to be able to have that be a part of, the story. And at that point, it was just really all like, what’s funny, what’s funny. What’s funny. And I think maybe the reason why a lot of things didn’t connect is they needed more heart.

Yeah, it’s totally different thing. I could totally see it. I mean, if you’re, if you’re doing a show, I mean, you’re, you’re in this space like this big, right. Typically, you know, and if you’re a performer like you were just, you were crazy, you were jumping on the stage and doing this and that it’s a different right.

Completely different, you know, dynamic. now what’s interesting though, is you hosted SNL, you hosted Saturday night, live your two-time guest. Correct. Two-time guests on that. Yep. Not, not a lot of people on that list. So I, I need to ask you, what was that like? What was the experience like hosting SNL?

Well, we talked earlier about like, okay, what was the breakthrough moment? And then what was the validating moment? You know, hosting Saturday night live getting a call from Lauren Michaels. It was about a week after retaliation. Charted. It was like Jay-Z and me in that top four or five. And I remember thinking to myself like, oh my goodness, you know this, now this is really gonna, you know, go into some territory that I, I, you know, maybe wasn’t quite anticipating what happened so soon.

And I was in Vegas. I was in at the Vegas comedy festival and Lauren Michaels got my number and called me in the hotel room and said, you’re hosting. I remember I was. I am when, and he gave me the date standing on the stage at, at Saturday night live having watched, you know, Martin short and Billy crystal and prior Carlin, Steve Martin, everybody went through that, turn style.

And for me standing out there and, and, reaching that, you know, what I thought was the pinnacle really, It gives me chills it. I, when I think of it right now, I, I feel like I’m still there in it. I, I, I can recognize the feeling of, this is where hard work can take you. Your hard work can take you to the, to the door and then into the place that you’ve dreamed of arriving at.

So damn cool. Is there anything, you know, now that you wish you knew before you started your career, like maybe, mistakes lessons learned, anything you can think of off the top of your head? Well, you know, I, I live my life feeling like nothing is falling apart. Things are always falling together. And even in some of my worst, you know, dire, capsizing moments and I, you know, I’ve had my share, you know, even, even as.

A kid and growing up with, you know, alcoholism and, and kind of, dealing with early childhood trauma. I choose to look at even some of the, you know, missteps as well. I, I needed to step in it to become, you know, more empathetic or more, you know, understanding, mindful, whatever it might. I think that more than anything, it’s such a great question, cuz I’ll tell you what comes into my heart.

When you, when you ask it, it’s always about time spent with people. I love it’s always. Oh, I wish there was a way that I could have realized sooner people like Frank, you know, obviously, my mom and dad who, who both succumbed to cancer right around that time. Right around that time. When I, I had been riding on this enormous, you know, wave, I think it always comes back to, I wish I had the ability to, to recognize how precious that time is and share more of it with those people.

That’s all. But you know, that’s again. That’s why day to day in life. You have to say your, I love yous and recognize that, it’s as important as working out or proper nutrition or storyboarding. Your ideas is telling people that you care about them, that you need them, that you, desire them to let more people in and to be able to share your wisdom.

I share my failures. I share my success. So that it’ll, it’ll hopefully inform somebody who is going to have their capsizing moment. It’s not preventable, but then will they have the equation to realize it’s for the best that I learned, this, this lesson it’s for the best that I faltered so that I could find something that maybe wouldn’t have been apparent to me.

Man. I love that. And I hope everybody’s paying attention to what, Dane said there it’s profound. I mean, when you get older and you look back that just comes with, with age and maturity, you think about how precious time is in the sand and the hourglass. Right. And as we get long in the tooth, as I say, Dane, we think about the stuff we spending time with, right.

Forever. Yeah. It’s true. so I appreciate that. I know you got, we’re gonna talk about, what you’re doing now. You got some crazy stuff going on, big, special, which I, I wanna unpack. but so far. I know you’re in the middle of it, but so far, do you have a favorite career highlight? Ooh, a favorite career highlight.

Yikes. well, you know, I directed troublemaker. That was my last special that we released in 16, 17, and it was so fun to, you know, prepare it, write it, finance it, produce it, and then direct. To get into that edit bay and to see this thing, completed with everything from the first inception of my ideas, to how it’s going to be presented the, the color, the sound mix, the, the font for the opening titles, getting Weezer, who I was a big fan of to, you know, provide a, so like every element of that is, The larger truest, most organic version of what standup is, which is I thought of something funny.

I wanna share it. I did. You laughed and that’s all you wanna do on any given night as a comedian. So especially usually gets away from you. Sometimes there’s other, you know, people in that, you know, production team or maybe a network owns it, or somebody else is gonna have some say or that’s too. We wanna cut that.

That was seeing something all the way through it, you know, 28 years into my career, that when I watched that, I’m like, this is exactly how I wanted this presented. And I’m, I’m deeply proud of that. And I, and I look forward to directing not only more of my own stuff, I didn’t direct the one that I just finished, but I definitely will be directing more of my own stuff in the future.

And, and even now directing outside of standup has been, some of my most exciting mornings waking up realizing, oh, I’m at, I’m at the helm of storytelling, but now on a greater scale, Yeah, well, the way you describe it, like, if you are a creative, it would be rewarding, right. To go through that process.

Right. Of, of kind of like picking the elements that you want. Right. So as a true creative, I could see that. I’ve heard you talk about this too. I think it’d be good to get your perspective, any advice you have for up-and-coming comedians off the top of your head. You gotta keep your integrity. You have to trust your gut.

Your gut is gold. You have to be willing to weather. The storms of the closing door is loud. It echoes and you gotta stay there and you have to be ready because the next time you pound on that door and it opens you better have something to present. That’s well crafted and dynamic and speaks to your truth.

So that starts with keeping your, I. When you keep your integrity and you don’t try to give the audience what you think they want or give the manager in the back of the room or the producer or whoever that might be when you bring people into what it is that you are passionate about, you are setting yourself up for wins.

If you are. Bending your integrity, trying to be malleable to something else that isn’t quite where you wanna be or how you wanna be positioned or, or seen. But you’re, you’re gonna give up a little bit of that integrity for the possibility of popularity. Then you’re setting yourself up for forward moment in the wrong direction.

You may win. But you might look back down the line and say, man, I’m, my authenticity is murky. And the worst thing is when you try to get back to that authenticity, and now people know you as something that you’ve presented entirely different and you wanna change the narrative to know, but this is who I really am.

So to all the comedians that are taking that mic out for the first time, or first several times, keep that integrity, speak from the heart, cultivate your ideas. And always, always, always end that show on a real hard, real great lap or something that you feel like is it, they call it like working out an impact rep the last rep is the most important because muscle memory always end leave them wanting more with your strongest desire in your messaging that you want to.

That’s awesome.

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Okay. So I’m gonna ask you to unpack what you’re working on now with the exciting, special you’re working on in one minute. But first I do wanna ask you about, but you know, you’ve gone through a lot of different, you know, incarnations of career, you know, acting and in stand up comedy in the albs.

And, and I know you’ve been, you know, retrospective in introspective lately. what do you enjoy most about where you are right now? You know, professionally and personally, I think that. I’m most excited at, at, in year 31 that I’m as curious and as I feel like I’m as new as I felt then, because I’m always allowing myself to try something new and to hopefully add new, elements to my performance, whatever it may be.

So I still wake up just as kind of, it says glamorous the world of standup comedy as it was when I started. But now being the old bull on the hill, I feel like I can speak from a place of greater understanding. I feel like I can share more. I could talk about wins in the wind coln, but I could also with great confidence, tell you about where I was at my lowest.

Or made the wrong move entirely or was misinformed. And the fact that, I can share my power in that way. And I’m okay with however you receive it. That makes me feel, the most enthused, because I remember that kid who was so scared of his truth and who I was and how I look to people and how do people like me?

And do I even like me, I remember how convoluted that all felt as a kid. So to still have the same fantastical imagination. Coupled with the confidence to not only love myself, but then to share with you the things that are important to me, highs or lows, that’s not a bad way to start the day I like it.

That’s interesting. okay. So tell us about the special, tell us about the new, special what’s going on. When can we expect it? What are you working on? Cuz I, I know you that you put a lot of time and, work into this. This is, I cleared the room a little bit, but we were watching on the, the screen here, a version of the rough assembly of the edit.

I know it’s my best work to date. I think it hearkens back to the size of Vicious Circle or Rough Around the Edges, but I think it has that same breakthrough. Element to it is as Harmful. And yet it has all the things that I, I wanted to add the maturity, the introspection, that’s something I wanted in there.

I wanted the LPMs with introspection. What does that mean? Laughs per minute with still allowing people into the, the deepest parts of both winning and losing or failing and succeeding. And so for all those reason, Aesthetically it’s gorgeous. The team that I still don’t wanna say who directed it, but the people that I worked with are top caliber people.

And I know it’s the most beautiful, standup special that anybody is gonna see maybe in the last 15 years. So for all those reasons, I’m excited to finally put it out there in the world. Wow. And when can we expect. Well, what we’re gonna do is we’re gonna have a screening out here at my agency in a couple of weeks.

We’ve got, most of it done. There’s a couple things that we’re, toying around with, but, then we’ll bring everybody in buyers. And another thing talking to Y like young artists, you know, you wanna own your IP more than ever your, your intellectual property. If you can make something yourself, you can pay for it yourself and then copyright it yourself.

And it’s more than ever an. To create it and then share as opposed to like somebody’s gonna come in and pay for it for you and be your partner. But that means in perpetuity, you might not even have control of your own image or your own content. That’s very tricky. It’s a slippery slope. So I did it all in house and nobody has seen it except for a couple of people, obviously the crowd that was there and my production crew, but I cannot, I’m chopping at the bit to finally start showing.

To all the streamers and some of the, the, the people that have been, calling and asking to be a part of the screening, man, I can’t wait. I can’t wait. I can’t wait to see. I’m excited about it, man. Thank you honestly lot. Appreciate it, debt serious. and you know, when, when that happens, we’ll make sure we, we, we re-edit the show notes and put the link in there, something to get it.

Cool. I’m excited about that. okay, so here’s a question. what do you do for fun? What do I do for fun? Oh my gosh. Fun. We’re in the personal development, section here. Well, I have a, Rhodesian Ridgeback puppy and she’s about a year and a half my girlfriend. And I probably spend more time.

Well, I have, I have another dog chopper who I’ve had for about six years and we’re real homebodies, man. My girl and I, we like to, we’re like, you know, we’ll binge watch. We just went all the way through. Oza. We’re about to start Yellowstone mm-hmm we’re watching, open range with Josh Brolin. You know, I think that the one thing that has remained since I was a kid all the way till now having just turned 50 is I love entertaining the masses.

And then I love that meditation of not needing anything more than just home. I don’t chase anything. There’s no, there’s no party over there that I wanna be at. You know, my girl and I love to create cultivate. And then we like to enjoy that. in other words, we’re boring. we are, we have our game nights.

We have a few people over for game night, but we like to keep things pretty, you know, pretty mellow. And I, I like that dichotomy of being able to go out and do extravagant large scale shows. And then, nothing makes me happier than couch surfing and, having a Sunday fun with my girl. Sounds fantastic.

I like it. we’re roughly the same age. The, what’d you think of Boba Fett? I like it. I like it. Yeah. I, you know, I, personal preference, I always loved the tone of empire strikes back and I wish that these shows could even be a little bit. darker. I wish that they would allow some of the storylines to dip into things that are right.

A little couldn’t couldn’t agree more. I mean, empire strikes back was the best one because it was dark, you know, mental, but the show looks incredible. The, the, the people working on the show and the, the effects and the way they, they make these show. It’s like, they’re gorgeous. They’re they’re, they’re awesome.

They really are amazing. Okay. That’s right. Here’s a question, Dane. Last two questions. If you could have dinner with any three people in history, pastor present, who would they be and why Elvis Presley? why not? Right. It’s like, are you kidding me? It’s. You know, what he experienced and how he experienced it.

You know? Yeah. So that’s an easy one. pastor present, you know, I, I wish I could have a dinner with my, my mentor, Frank. I wish he could have seen me. Finally come to a full realization. You know, he saw me as that kid who was still had a lot of fear in him. So I missed Frank and I wish that I could, break bread with Frank one more time and then probably have to be like, I don’t know, maybe somebody who’s like, you know, I wanna have another dinner with Steve Martin.

Yeah. he’s so he’s so busy these days, but it’s like, come on, Steve hit me up. Let’s go out. Wow. So what, what a dinner table that would be, I forces you to think. I like that question. you know, it’s, it’s a fun one. now the word legacy, we’ve been hearing from a lot of influencers, creative celebrities, successful entrepreneurs.

Now, what is your legacy like when all said and done, what does the Dean Cook legacy look like to you? Wow, man. I mean, I definitely feel like a big part of that is. Going to be the comedy, right? The comedy that hopefully people will enjoy for, I don’t know, for however long, a nber one, it would be comedy, but I definitely am, grateful, very grateful that you know, whether it’s clubhouse or TikTok or Twitter spaces or whatever it might be.

I can appreciate that people come to me and they come to me all the time and, and say like, how does this work for me? How, what is the thing that I’m missing here? That I have this tool, but something’s lacking. And I love that. people look at me as a person that came through that early incarnation of, this digital age as, as one of the kind of early pioneers of what worked, what didn’t work and where it’s come to.

It’s great to, and it’s great to be bringing the next incarnation of my standup and using now all of. Yeah, I love that, day and my man, what an awesome interview. I really appreciate you, taking time with us today. I did. With two minutes to spare. I did it I’m a master, I’m a professional podcaster.

I gotten to know you a little bit, you know, just on the social channels and, and whatnot. That’s right. I think you’re one of the most passionate, articulate, intelligent, funny dudes. I’ve ever had a conversation with for real. so I really appreciate, you and all you do, I’m really looking forward to, what’s next.

I’ll be paying close attention, and to get your perspective. On, your career and what’s happening, where do you want the people to connect with you? What do you want us to? You want them to follow you on social, et cetera? First of all, I appreciate that man. And I would love to make sure that once the special’s out there, then we can kind of sit down and talk about the house and whys, because I, I think that it’s gonna move the needle in terms of what in a standup comedy special should be.

So I look forward to talking more about that with you. Once it’s out in the world, all my socials are, are the handle, Dane. I’ve been doing a lot more on TikTok, cuz I like the live feature on there. So I would say primarily find me on TikTok. If you wanna back channel chat with me, that’s still Instagram.


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