What actress did Leonardo Dicaprio film masturbating in front of a crowd at a party while he whispered in her ear in the 90s?

Candace Bergen

Estelle Winwood.

I'd bet anything it was Annie Potts.

Faye

Dicaprio is an unsavory sort, I wouldn't want to know him.

Tracey Gold

Sharon Stone

Candace Cameron Bure

Roseanne Barr

Gloria Stuart??

Teensy and Weensy

Jennifer Love Hewlit

It would have to be someone close in age range to those lil pussies. So I guess the dominant ones would Leo, Tobey, Ethan and Jay R Ferguson.

If it’s someone still popular today, that boots the Growing Pains crowd. I don’t think anyone on Evening Shade would do it, but Marilu Henner was always full of surprises.

Tracy Gold

She was masturbating because she found it so hot 🥵 watching Leonardo DeCaprio get fucked by a muscular well hung top.

It was her party trick.

Mindy Cohn

Barbara Bel Geddes

[quote] What actress did Leonardo Dicaprio film masturbating in front of a crowd at a party while he whispered in her ear in the 90s?

Good Lord, John Madden would need a whole wall to diagram that mess of a sentence.

R19 being a substitute 4th grade English teacher in 1963 was highpoint of your life. We get it.

It was supposed to be Lucy, but Gary talked her out of it.

R20 - It's sad that you have such a limited imagination.

R22 we can happily imagine you gran.

This was bra-less Bonnie Franklin's standard party trick.

Ellen Pompeo I think...not sure

Estelle Getty

One of the Friends gals.

Claire Danes?

Heather Locklear.

It was Olivia de Havilland

Bea Arthur

She was almost raped later that night after the party r17

I can’t open OP’s YouTube link.

[R32], she was prepared and was able fight off her attacker with her car keys and lollipop sticks.

The only actress Leo was rumored to have fucked around with in the 90s (he's pretty much exclusively gone for models since the beginning) would be Claire Danes at the start of filming for Romeo + Juliet. She began to hate him by the end of their time together, but I remember a ton of rumors that they were briefly dating behind the scenes back then. She was also a TV star and is still a household name.

So my bet is if the rumor is true, its Claire.

I can’t picture Claire Danes masturbating.

Tara Reid

Paris Hilton

[quote] was one of the biggest TV actresses at the time and still a household name.

Tara Reid and Paris Hilton? I don’t think so.

Dame Judi Dench……or as Leo called her Judi DRENCHED!!!!!!

They always exaggerate when it comes to things like this. Paris Hilton had a TV show and she's a whore. Gotta be her

It want in the 90s.

^wasn’t

Tina Yothers!

Tobey and Leo seem nasty, I know it's wishful thinking but wish they could go down with Diddy

It's Claire Danes

[quote]I can’t picture Claire Danes masturbating.

Perhaps that's why they felt they needed to capture it on film. Of course, she would have been about 17 at the time--would that constitute child pornography in the 90s?

Yup r47

That may constitute why Leo is trying to stray WAY away from all this Diddley shtuff. Claire was under-aged at that time and very well-known for her "My So-Called Life."

Apparently, they briefly dated during the filming and broke up shortly (either within the filming or shortly thereafter).

She sounds like the likely candidate for this.

Also why Ethan Suplee said he'd destroy any vids/pics he took before handing them over (I was able to listen to the vid upthread). '

Ethan didn't want to be implicated in child porn charges.

Why do people refer to celebs as “dating” when all they’re usually doing is fucking until the novelty wears off?

r50 detracting who the actress is...

Meghan Markle!

Americans are so obsessed with sex and view it as sacred and dangerous. It’s ridiculous.

Tyne Daly in the Library with a can of Crisco.

losers offering fake names

I can't imagine DeCaprio fucking anyone. He is totally asexual looking. 90's Leo was childlike and elfin and then, boom, everything went gelatinous like his bones melted. So blah.

Leo was probably molested. That will fuck up anyone’s sexuality. And he does have sex but the report back from women is that he just lies there - like he has to do it, not wants to. He probably like to cuddle with other men mostly.

[quote] Leo was probably molested.

Was it Kirk Cameron just before he found Jesus?

R23 - Thank you for proving my point. And not just a limited imagination, but clearly also a neurotic disdain for basic grammar. Sad.

Since it was someone he wanted to humiliate and not fuck, I assume she was either older or not that attractive. This is actually juicy gossip. Of course, 90% of the “guesses” on here are troll jokes.

[quote] Since it was someone he wanted to humiliate and not fuck, I assume she was either older or not that attractive.

Or simply female.

R36- Are you a FRAU?

Leonardo DeCaprio is a homosexual. There were no relationships with any women.

Gabrielle Carteris. And she wasn’t masturbating, she was clearing out the cobwebs.

The only dame with the guts to do this is Helen Lawson, baby! Yeah, I "pressed the flesh" in front of those boys. That pipsqueak Toby couldn't even get it up to plow Leo. I don't blame him. Leo was so fast and flabby, Toby'd've done better to fuck a nice piece of veal.

When I was finished I rubbed Leo's face in the Lawson snatch and he started whimpering. What a wuss!

My So Called Life was a ratings bomb in its initial run. It gained a big audience later and I am still not sure Claire Danes is a “household name”. I don’t think Gen Z knows her.

Sara Gilbert

Ann B. Davis

R66 that would track…except Sara must have been masturbating over female models that were there.

Oddly, I thought of Hilbert too knowing she was part of that group. But she’s obviously still friends with Jay R Ferguson.

Actress, R44. The article clearly states “actress”.

[R68] I read the book and it was a young actress who was head over heels for Leo, so probably not Sarah Gilbert.

R65 well it’s someone this 50 year old guy considers a household name so someone millennials and gen x probably know. Clair Danes is a good guess..

Claire Danes is a good guess. There was a lot of buzz surrounding his treatment of her when filming RaJ. She was hurt and she spoke about it in interviews. It was reported that he called her ugly and degraded her, which tracks with what [R60] hypothesized.

Sorry, but I do not buy Claire Danes masturbating in front of a crowd at a house party. This never happened.

He's a dirtball. Whoever it was, was probably on that 90's MDMA.

Katie’s Holmes, Felicity, Sarah Michelle Geller, Tori Spelling.

Spelling

R65 Of course Gen Z knows her. Romeo + Juliet had a huge Gen Z resurgence in popularity, as did My So Called Life. And Homeland made her a household name for the Olds. Millenials always loved her for MSCL, R + J, and Little Women. Plus Brokedown Palace introduced them to Moby. She's a household name. Trust me.

And since Leo always goes for infants, even in his elder years, I can absolutely see him messing with a (plain looking, relative to his usual supermodel fare) teenager six years his junior who he can tell has a schoolgirl crush on him, and degrading her just because he can.

Maybe it was Jared Leto. Gay or straight, who wouldn't want to see that!

R79 Nice try Jared..

Isn't Jared like 60 years old? His dick must look like a gray curtain pull by this point. His "Portrait of Dorian Gray" isn't in the attic, it's in his pants.

Susan Dey

Lorna Luft

[quote]Leonardo DeCaprio is a homosexual.

Are you Karen Walker?

Roseanne

R85 made my asshole pucker 🤢

Sandy Duncan

R87 - Was she fingering her eye socket?

"Nepo-baby"

George Clooney

Anna Magnani

Angel Lansbury

Blythe Danner!

Christina Applegate

Ruth Gordon

Christina Applegate is a great guess.

I'm surprised at least one of his model girlfriends hasn't gone the press and spilled every weird detail about him. I'm not a lawyer but I heard sexual NDAs are basically worthless. Maybe they get a check every year for staying silent.

Whoopi Goldberg

Why does anyone care? She got her rocks off. Good for her.

Christina Applegate didn’t hang out with that crowd. She was a Viper Room gal.

Keri Russell

R97 Many have. The consensus between them all seems to be that he's terrible at sex and kissing--lazy, awkward, selfish, and weird. He wears headphones during sex so he doesn't have to hear his partners. Basically, he pops the headphones on and listens to music, telling the confused girl to "just keep going", while he lays back and vapes.

He, by all accounts, does seem to fall in love (or whatever his version of love is) with each of his fetal girlfriends and is kind and thoughtful during this time, but the moment they turn 25, he loses all attraction and dumps them within a few months.

Olivia de Haviland

Links R102? This is fascinating! I had no idea.

Ann Miller

That fag loving whore, Jodie Sweetin.

One of my best friends is besties with Jodie Sweetin, R 106. So I've hung out with Jodie Sweetin, been to her house. She's got a thing for bad boys, and has substance issues. So who knows what she's done in her life. Her daughters were begging me for attention when I was at her house. I mean, jazz hands, sharing their homework, dolls, everything with me. I like kids so they could tell they could get juice from me, and they were literally draining me dry of any and all juice. I shudder to think why. I know their own dads both suck so I guess that's a good guess why. They would not leave my side.

Who cares? Ethan Slurpee looks very good nowadays.

Applegate was before Leo and his pussy posse. It was probably that Punkie Brewster chick.

OR Juliette Lewis? CHRIST, I hope not.

Esther Rolle?

Spelling makes a lot of sense IMO. 90210 was huge and she is still well known, if not for anything good. She also seems insecure enough to do it.

R102 he's gay. He's not having sex with these girls

R104 If you just Google "Leo DiCaprio bad at sex" you'll find PLENTY. Seriously, his exes sing like birds.

That's good gossip, R107! I like Jodie, and that's sad that her kids are seemingly attention starved. You sound like a good human, listening to them and giving them your time.

R115 many more parents than you would think pay no attention to their kids other than to meet their basic needs. All the attention goes to their phones.

R107 - isn't she on record saying she had drug and meth problems and has been clean now for years?

R73- She was so attractive in The Family Stone but remember she was only 25 years old in that movie. Her looks are gone.

I think I saw this scene in the Guys Gone Wild 46 DVD.

R113 You've been screaming that from the rooftops for AT LEAST two decades, right? At this point, you don't even believe it.

[quote]He also insinuates that Leo/Toby were more than a little close in this book and also in past tweets.

I think that Toby's mother also talked about this...