Let's Be Friends with an Ex...with Rob Weiss (Part 2)

Published Apr 18, 2024, 4:00 AM

In part two we find out how Rob proposed to Shannen, or at least TRIED to propose. The ring he couldn't afford at the time, asking her parents for their blessing, and why they broke up and got back together. Plus, we dive into the 'Entourage' character inspired by Rob and why he didn't play that role in the Emmy-winning show.

This is let's be clear with Shannon Drny.

I think for someone like you, it must be extremely hard because you write, to sit there for two years and write a show and write out you know what would happen over the seasons, and then go out and pitch and like you're saying, if somebody doesn't like it, it doesn't get bald.

It's two years of your life.

Yeah.

Well, the only the MBGA wars if you did it and you didn't get paid for it. So fortunately on the project we're out with now, Skydance bought it from us, so you know, at least where compensated for the grind. You know, I think that, But when.

You were younger and you were writing, you weren't.

Yeah, listen, I still I work on for the The way that I ensure that I will not spiral and spin off the planet is I have to work on ten things in once. The reality like as long as I am you know, spread thin, and I'm focusing here, focusing there, throwing a little time at this, and they're kind of all rising up like in terms of you know how substantial they're be coming and how you know how they're getting worked. Then I'm happy if I spent two years working on one project and then took it out. You know, yeah, I probably I would not fare that well.

With the rection the draft board, you know.

No, because you know television.

I mean back in the day when I was writing, I was writing movies, right, you know, and I was trying to figure that out, and I was still a young writer.

I've now been a part of I mean.

One hundred and probably like one hundred and fifty hundred and sixty episodes of television. Right, So my brain I ballers how to make in America. But like my brain for sitting in a room and looking at story in the way I see it, and story and beats and how to drive it in the characters.

It's a different kind of muscle for me now.

So I'll still have like beat sheets and I'll still put things up, but not I don't.

Rely on that like that, you know what I mean.

It's like it's become like a little more of a model in my brain, or a little more format at least the kind of shows that I named.

Even though they're all different, they have.

Similarities that they're slightly tonally different, and they're different settings, different characters, different experiences, this one.

I'm out. It's a little bit different. It's a little bit longer.

It's a little more of a drama with comedy as opposed to comedy that's dramatic. So I mean, it's still dramedy. But I'm it's fucking dope. We'll see, We'll see what happens, you know what I mean. I mean, I don't cont trouble with the university, you know, so unfortunately.

Sorry, I'm going back to our relationship. Do you remember the birthday party I had? What was it like, I can't remember what bar, but it was off of Klinger Oh, the fight thing and the fighting.

Yeah.

He rolled in with what was his name, Danny.

Boy, Danny Boy from the House Openion.

Yeah, Danny Boy, and a bunch of other dudes.

Eddie Donaldson.

Well that was kind of crazy because first off, we were only dating like ten days?

Was it only ten days?

We were only dating because it was your birthday party. We had started dating on April Fool's Day. I was at the bar.

It was against the Clemishes.

No, they were surrounding that guy, Greg Vance. Yeah, he was surrounded by a bunch of guys and I just remember him looking over me like with this weird look, and I'm like, what's up?

You know.

So I walked it and I'm like, yo, what's the problem. And then I heard a voice from my behind my right, which, by the way, I wouldn't have a walk into that scenario now, like and the way I did them, but again as a kid, and I just heard some guy going like, oh, now he's got a problem. And I turned my head and I just got blasted with a head butt on my nose. But then it turned into just some melee that was like on the globe, and then Danny Boy came in and it was crazy.

I mean, it's filled out onto the street.

Yeah. Well, we were a lot of guys. They were like ten of us.

Yeah, you rolled in. You always used to roll around with like a lot.

I don't do that anymore, man.

That just cost me a lot of invitations to a lot of like really cool things, you know, because they beg on Rob'son, were coming like twelve dudes, you.

Know, right, Yeah, I don't really do that anymore.

But I'm very low key. I don't really go out anymore. I told you i'd stopped drinking like five years ago. Like I'm just like happy, being like an old dad who looks younger than he is. That's it's all I want, you know. What I mean is to feel strong, feel good. And by the way, I say that mostly in relation of being a dad, but like I'm like doing all this stuff with my song. It's so fun, you know, and it's like I try to really embrace like the positive of that energy. You know what I mean that I have one is an example too, you know, like I didn't want my son porto. I love drinking wine. I know you like wine. I love the red wine like Bordeaux.

I love it.

But it was like, you know, those few times where it would be like when he was I think I quit drinking. He was like probably two three, but I remember being like slightly.

Hungover and I went out and I had like.

A babysitter, and then he said, Daddy, I'm hungry, and it's like seven am and you're going hungover, right, yeah, okay, but I got you. I was like, man, I don't want my kid to see me like this, like I want to kill the generational drinking.

You know.

So the example you're setting for him now is a really good one to.

Be in that area. Yes, in that area. I'm sure, like I.

Am looking at a couple hunder grand in therapy at some point over something that I'm gonna be blamed for, and that's just life, and I think that's reparent.

You know.

At some point I remember, at some point in time me with my dad and challenging him on everything and him looking at me like, wait, you think it gets smarter than me. You know, it's like you have that thing. And then you know, by the time my dad got sick and he passed away, like we were cool on every level. I got him, I understood, you know, and I stole, you have my dad all the time. Come into my head and I look at my son and I go, if that's not my dad reincarnated, I don't know what the hell it is. My kid was waking up like last week, he's like five month days to Vegas right first spring break. I go, dude, what's were you in Vegas? You never even been to Vegas? I just want to get there and win some money. I go, you're eight years old, you can't gamble, Like what are you talking about? And he just does things that is so my dad.

Photos that I've seen of him where you know, you have like guys over Yeah, and I guess it's you taking the photo. But there's like a head tilt thing in some of the photos that he does that that.

Really reminds me of your dad.

Really.

Yeah, it's so bizarre.

There's like there's just and it's not all of the photos, there's certain there's certain ones where he's just got like Carl Weising.

Yeah, he really, he really does. I don't.

I don't, you know, it's not like it's I'm oblivious to myself and I'm totally unseelf aware. I don't believe it's things that my dad passed to me that I'm passing him, like there are direct correlations between him and a deceased man that he never met.

Yeah, and you just.

Go like, you know, I mean, I mean, come on, man, we all got to admit, whether we can, it's tangible or not tangible, it's more than meets the eye.

Here.

You are a three time Emmy nominee your work on Entourage.

Well yeah, but that's collectively the show was nominated for Best Comedy.

So your break came in nineteen ninety three, when you wrote and directed the nineteen ninety three film amongst friends.

That's right.

The film was well received at film festivals. Yes, and you were nominated for the Grand Jury Prize at sun Dance.

That's right.

How did I not know that?

Yeah?

Well I was in competition, so but I was also nominated that movie. I nominated some other great festivals like Dautville, Edinburgh. It was like it was well received, you know. Again, like I said, it was just good. It was for like a kid to make a movie. It was it had a lot of heart and it was you know, and that's what it was really driven and fueled by all the people who worked on it were just people that were trying to do something. It would never really done anything, you know, and there's definitely promised them. Maybe we'll capitalize on the promise someday. I don't know, you know, we'll find our path like the things that you know. It's like when you're young, you're like, I wouldn't be the Academy Awards I want to get Like yeah, like I haven't even thought like that in so long, even like we were nominated.

For six years straight for Golden Globes with Entourage.

I'll never be ungrateful for it that it's amazing to have accolades. More it's for me more amazing to have fans, like of a project you work on. There is nothing better to me than like ballers, airing and seeing people live to eat about it, people dming about things they love. That to me is the greatest thing more than other people in the industry, Like recognizing the work you're doing.

And it's cool too, but it's not as important.

So when you're young, you have this vision of what success looks like to you. Right then you get older and your vision changes, right, Like success for me is being able to afford to educate my son, feed them properly, for me to be able to train and eat where I want to eat, well.

Would I want?

You know what I mean, Like a little bit of freedom, Like that's what's important. Like the award thing. The nomination is cool, but it's cool, but it's not but it doesn't drive like I'm not like making projects going like, oh, how's this gonna be received?

But I don't think anybody thinks like that anymore.

I don't think anymore.

Used to like that was a very big deal if you were nominated for something. I remember when like nine to two zero was nominated and we all went and then like Jason Luke and I presented.

At uh it was it the Emmys that we presented, and it was so exciting.

It's like, oh my god, you know we we we made it.

Yeah.

You know, there were a bunch of those moments back then being on the cover Rolling Stone magazine, like those are all those funny moments, whereas now I remember.

That I was hanging in the TV room in your house. Yeah. Yeah, it was cool man.

Yeah.

And I think also the more successful people BECOLM, the bigger the targets they are, you know what I mean.

And I think people are just like.

Light down to quietly make dough and live a good life.

You know. I think like we.

Live in like I'm saying, we as just society, Yeah, society live in this just era of constantly just taking people down. And I'm not saying who deserves it, who doesn't deserve it, But you're just inundated with negativity all them.

Constantly, man, and it doesn't really matter what build them up to take them apart.

And you're just like holy shit, you know, and you're like.

You gotta wonder for some of these people, Like obviously there's some pretty serious offenders out there that deserved it.

But you gotta wonder about somebod these other people that are just like, oh man, what the that I get into this for? Like what you know?

Well, I mean there's just there's that.

There's there's the bullying that just because you're the public eye in any way shape.

For this one like that they didn't lose weight the real and she just like.

It's nobody's business.

It's crazy, like, let this person live their life the way that they want to as long.

As they're not hurting.

Trolling is insane.

Yeah, by the way, Okay, So for people that don't know, Rob is from Long.

Island, originally Brooklyn then Long Island.

Uh, I didn't know that you actually went to school with Doug Allen.

Yeah, we went to Woodmare Academy together for a year. I was a year older. But then he went back to I think JFK and.

Merrick and he said that, uh, you were the inspiration for the character Billy Walsh on.

T that's right.

I was, yeah, well it's kind of honestly like the real the real truth story was that in season.

One he asked you to play the part.

So but So basically what Doug wanted to do is he goes, why don't we make the director Rob Weiss and he hasn't made a movie in a decade and he wants fins for the movie. And I swear to God, the whole time I was working on this show season one, I'm like, like, this is this is over. This is over. Any hope I had for careers over. The show is gonna be horrible. Who's gonna watch this? Like this is a disaster And it's crazy because we were actually enjoying the process of writing it and I was super excited to do it. But for some reason I could not connect to how an audience was going to connect to the show. I did not foresee it. Doug always had an amazing ability in when we're crafting story or even dialogue and knowing how people are going to receive what is being said. I didn't have that skill set when it started. I was more of the stream of consciousness guy, like I could definitely construct a good scene, and I and I always have like good dialogue even amongst friends, that sharp dialogue, but you know, in flashy. But I didn't have his insights, so I really didn't believe that the show was going to be anything. So I was like, no, Bro, I don't want to play Billy walsh Man. I don't play rob Boy. I don't want it to be Rob Weise, and I don't want to play you know, a character. But it was it was kind of like a mashup of me and the indie guys from the nineties that kind of will like consider to be overly precious and nuts, like me Vincent Gallo, Like there were a handful of guys that they would reference that they'd be like, oh, that guy was a lunatic, or that guy refused to do this, you know.

But what's really interesting is that I didn't know that Doug wanted you to play the part.

So this is crazy.

You were you.

Do all these things about that's what happens, But you were my favorite and amongst friends, like your thing is.

Having it over here, is helping it over there, remember that whole thing like you were.

I just remember watching it being like that guy's hot, Like you were the one that I that I liked, and I thought that your acting was really good.

Nice welcome.

I wish you told me this twenty five years ago, and I had back then there might have been another revenue stream for me. You know, I would to throw myself at something like improv classes.

You can do that.

Now, I think that moment's passed me.

Rick has just started acting.

Well, he jumped in Danny A's movie right Who I love also, and Rick is a natural. I think like you could cast me to play a version of me. I'm happy to do it. Me like getting ready for headshots and submitting it's not happening, man, it's not happening. I just want to get my shows made in the movie I'm writing, and that's like it, you know, just focus on.

That path, all right, I'm going to bang out a bunch of these. What was your first impression? Was it attraction at first sight.

Of who Me?

Yeah?

Well, like I said, you were already you were already a star.

So I was watching you at home, I'm on my TV and I was like, yo, that's like my dream girl, you know what I mean. And I met you and I was like crushy crush, and then you know, then the hell yeah, man, I was like in you know, and you were fun man, you I mean you were spiciest, but you know you were fun with like like I loved hanging out with you. You know, back then you were a cigarette smokers be like man's girl, smoke cigarettes like a fighter pilot.

You got in between what's up?

Yeah, you were very gangster and swagger. Gangster but sexy. Great, great style, great aesthetic. Even your home is beautiful, you know, like amazing cook.

You know you would like you know he's a solid.

You know you'll bounce back.

From mis divorce. I faith.

I'm only teasing you know, you one hundred percent will if you want to, you know, I mean I'm.

Over it, like oh no, like I'm over it, like.

You're over the divorce. Yeah, like you're not over like relationship.

No, I definitely want another relationship, right, I just don't want married again, but I definitely want another relationship. I like, I enjoy having that best friend you know, and yes, I have best friends, but it's different when.

You're in relationship. I told you it for me.

That's why I'm saying I'm like fifty to fifty because I do like that. But I also know I do better in life, Like on some nights when I fucking take a bubble bath and I go to bed and I get up at like five point thirty and I just get at what I need to get at and I don't have to have any conversations anyway.

And I love that too, But why can't you You can still be in a relationship but have off nights. You know, that's why you keep your house. The girl keeps her house. You don't move in together.

I feel like negotiating this is like you keep your house.

You if you want to come out to Malbu, come.

Out right, like it's times a week.

I think that feels like.

I think it only itoks like relationship in the sixties.

Yeah, that might be true too.

Maybe you're too young.

I don't I don't comment don't, but I don't really date that young anymore.

That's I also don't date that old either, So I'm probably I definitely think men should be older than the women they do.

You know what that what that age difference is? I don't know.

Like and again I'm not even like tripping on dudes that are dating women twenty years older than them, Like, and there's some super famous eyes out there that have wives that are like twenty five years older. Everything is to somebody's preference. You just want to be inspired to have energy. Yeah, that's it.

I don't give it.

If it's like a seventyear old woman with energy or a thirty five forty year old woman with energy.

You want good positive energy.

The idea for me that I'm going to be in a companion relationship and it's like, oh, you know, we're going to cruises together like I'm half dead, you know what I mean?

Like I'm not looking for that fuck vibe.

Like I just I'm not there yet, you know where it's like, yeah, we see each other like you know every other someday and we dinner at four thirty in the after.

It's just it just I'm not ready to age out like that.

You know, Well that takes me out.

Now.

That doesn't mean I want a data twenty six year old either, you know what I mean. It just means I need like vibrancy.

Man. I need to keep moving like it's just the way I am.

You know, how long did we date before we got engaged?

I don't know. That's a good question. That was like.

Was it like two years? Then three years?

Then?

Maybe do you remember how you proposed and where we were?

I don't think you let me propose. I think I just give me a ring. Let's go, let's go, let's go. That was not like the most fun process, Like first off, I could.

Really say that.

Yeah, like I'll like, I'll go down the rabbit hole now because certain memories of popping into my head.

One I think it was on the trip where we were in Italy.

We also wound up in the south of France and this kid like walks past me and like a speedow and.

He's like, hey, Robin.

I'm like, holy, it's like a kid I went to high school with and his girlfriend's family with diamond dealers in New York. And you're like, yeah, we're gonna get engaged. I'm gonna be in New York next week, like doing let them in or something. We're gonna stop in and.

See the stones.

And you're sitting at a que and I'm standing behind you and your fingers are like this and they're dropping like five characters.

And I'm standing behind you literally looking. I mean, I'm like a broke ass kid and I'll stand behind you go like this to the girl. You look back.

So we got that guy to make a really nice ring. I remember I had to go out to dinner with your parents to ask for that blessing.

Which was really sweet that you did that.

It was really it was really sweet.

But I've been going out with you for three years or whatever, and we spent a lot of time with your parents.

You're very very close with your parents, Yes.

Extremely, like they're involved in everything kind of shit. Right, There's a couple of things that I like, I'll flag that, I'll highlight. One was like the parents were always around, which is cool, but I remember so I went to the palm with them and I'm like, well, you know, so we want to get married, and like they just started keeping concerns.

Me and I'm like, whoa, whoa, whoa. I'm like, holy shit, I'm like, what do you sir? I'm like a bedatia for three years? Where's this all coming from? Now? You know?

Did I give you the ring back?

Yeah? I'm sure. In fact, I've been waiting all these years to slide it back.

On the hand.

Yeah. No, I'm sure you did. You know you were good with me?

I was like, I mean, first of all, I can't say like I've ever felt one hundred percent financially stable and safe. Obviously, I've had some really great successes and I own a home, and you know, and there have been certain things I'm about to do. But you know, it was definitely a period of ups and downs financially, especially in my twenties thirties.

You know, It's just it was for me too.

I mean I got fired off nine from Now, I got fired off Charms. It was like, well that's.

Yeah, that was really the length of our relationship because I was with you right after you left nine or two and zero, and I think I was with you until the around time you left Charm.

You know you for sure were, because I remember.

And it's funny because she her her questions are actually like, right after you guys got engaged, you broke up, but then you got back together again, So what made you want to try it again? But one of the interesting points is that at some point I stopped living with you and I got the house on Marmont. Do you remember the Chateau Marmont. I lived in that house for you for a little bit. Yeah, No, I stayed in that. Yeah, that was the one right over Depp's house.

Right. I was a for like a year with.

You, and then we had those two English masters English Masters.

Yeah, yeah, so we were definitely together after I got fired from Charmed as well, because I remember, like a little show got offered to me, and but I had to move to New York for it, and I didn't want to move to New York. Really yeah, I mean you listen at that point in time, I'm in my twenties, it was like.

Special Victims Unit, man, because you'd be like you'd be on in sports teams.

Now, now, let me tell you I was an idiot for saying no. But I yeah, like I was young.

I was in my twenties.

I was in love. I you know, my whole life is an ulla. My parents were here. It was like I didn't want to leave you. I didn't want to leave.

Oh I don't remember that, that's crazy. Yeah, we dissed it.

Yeah at them.

I just remember you had like a lot of conflict, like your producers asking why we would go back together. It was like, well, there's the obvious, right, which is we had the connection.

But again, you have to put it in the context of that time period.

You knew the people you knew and where you went and what you coveted. We were connected, we knew each other. You could go out and date people and have you alliances. I could do the same thing and they're like, oh I miss Shannon. You're like, I miss Rob And then we're all still going to the same handful of places.

We're going to cross paths and we're going to link back up.

Now I think people like are just like, hey, this was great peace out and they're.

Like, we don't see them ever again.

Yeah, that and they've already laid groundwork with like three hundred of the people and crabs like I'm gonna go on this and like, I mean, we could go down. Like just the insane differences in the world of the way dating is now and how obviously transactional and everything has beclm me like and again it could just be very like an la thing, but like the stories and like the way it is is just not at all the way it was when when we were young and dating.

Yeah, there was something a little bit more pure about dating back then. Comparents Now, I love that you said it was very It's very it's become very transactional because I've noticed that I won't do names, but someone who you know is pretty much a serial cheater. But it's only with people obvious transactional. It's only with people who can help that person at certain times in their career. I mean, I'm sure there are people who obviously married and dated for money or for a job or for whatever. But for the most part, back then, it didn't feel so transactional. It did feel much more pure now, and maybe it's one of the reasons why we very scared dating.

People to some degree.

Except for you, I wasn't famous, but but like people, I understand there are certain things that are you know.

Like whether they're I don't.

I don't call it transactional as much as I call that opportunistic, where you're just trying to use it to continue building and leveraging. So that definitely existed back then. But there was a purity to the point where like if you met somebody, you met somebody you didn't meet somebody that has posted a thousand pictures of themselves that look nothing like who they are.

That's a complete avatar.

You've developed this like fantasy relationationship in your head with this other person. Then you meet and you're so confused as to who's showing up. But yeah, you have this thing and I just look around them just like it was basic and it was simple back then, But it was good for that, you know what I mean?

Like it also like it also felt like a.

Community, right, Like dating back then in Hollywood felt like.

You knew the people. They all kind of went to the same places. I felt like like there was a.

Sense of community, and you're kind of dating in the community. I don't know if that's the case anymore. I feel like the community is more global now, you know, yeah, the global dating community.

I agree.

How has Rob been supportive during the difficult past few years?

He hasn't.

That's I never heard from him.

Yeah, but like, what do you mean what happened when I miss No, that's not true.

You definitely I've been there.

You've definitely sent me text messages, you called, like when.

My kids came out my dad's funeral.

Oh yeah, but I remember the cancer diagnosis. But you were married, so I assumed then. You know, one, I like to respect everybody's space, Like you don't need likeing X hitting you up.

When when you're married.

Right, He's like, oh, like, and that guy didn't seem like particularly like all loose and cool. You seemed a little stiff. So I mean, I'm like going to what's he writing for?

You know. That's number one.

Number two is you know, like people going through these life changing events of such significance, which are scary obviously, Like I think I wrote you like, hey, Senning, you love. If you haven't need anything, just know, like you know I'm here because I'm not walking in your shoes, and like I don't know your experience and I'm not going to make your experience about me. That that experience is just to say to you, like I'm here for you. You know, if you should need me, if your husband should let you down, hit me.

Hit me up, I got you. I got you girl. But you know, like, but so I think, like there were a couple of.

Times I did that, you know, and then there were all the things I learned at the same time other people did, like when your cancer came back, and I remember being devastated by that when the whole thing happened with the fire and watching you have to go on one of the morning shows which I watch, you know, the Today Show I think is on Chound four, This one I watched. But I saw you on a show where you felt like you had to share this new chapter in your battle with cancer because it was going to come out in this insurance case, and that was an awful thing to see. First off, anybody have to do right, but somebody that you still feel connected to, you care about, you know, like you don't want to watch somebody you have to go out there and put themselves out like that, and you know, and it was uncomfortable for you.

It was sonder because I hadn't. I hadn't like I hadn't really faced it yet, so I was still coming to terms and grappling with it. So then to actually talk about it with a stranger, it was very, very, very very emotional for me. I mean it's I can't even watch that interview. I think I saw, you know, a clip of it, and I I wanted to climb in a hole. It was really uncomfortable.

You know, you've been through a lot, man.

There's nothing I'm going to say that's going to take that away or make it better. It's your experience, you know, and it's a it's not been an easy one and an easy path, you know, and it's not.

Yeah, I mean, it's much respect props.

To you, you know, for for and I said this to you before the started, how important you are for other not just women, but people, particularly people that you know were part of that same generation watching nine or two and zero, and we're going through similar experiences and how they relate to you, and how you're leading people through by sharing your experience.

You know. That's a thank you. And you're pretty spry. Man. You got you got like a lot of like.

No, I got so much life left in man.

Good. Yeah, it's pretty clear, you know.

So I'm not going anywhere.

Yeah. I don't think so either.

Thank you, Thanks you guys for listening to it.

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