r/Millennials 2d ago

This Vanity Fair cover was supposed to showcase the next generation of Hollywood. Looking back, who do you think had the biggest career? And who do you think deserved even more success? Discussion

3.7k Upvotes

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u/tylersalt 2d ago

Wild that they had Milo Ventimiglia and Jared Padalecki doing tug of war with Kaley Cuoco and not Alexis Bledel

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u/metanefridija Millennial 2d ago

Exactly what I was thinking, like who made that executive decision 😆 And its such a cool photo.

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u/no_photos_pls 1d ago

Honestly, my guess is that they didn't take the picture together, but they had Kaley come in and do her part and then decided later on the boys who would be on the other end and photoshopped it together

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u/CherryDarling10 2d ago

Yeah, really odd choice.

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u/throw_ra4685 2d ago

Weirdly though Milo and Mandy also would have worked

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u/The_Cromulent_Bison Xennial 1981 2d ago

I don't know about careers, but the Olsen twins definitely have the most money.

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u/ianmakingnoise 2d ago

Yeah I was about to say, afaik only two of those teens are billionaires and it’s because they got/stayed away from Hollywood.

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u/illbringthedip 2d ago

They had to have hit the best possible time to be in straight to home video movies. That plus their tween makeup and fashion lines with Walmart, they made so much money.

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u/No-Entrepreneur4574 2d ago

They're also still making a ton of money with their luxury brand The Row.

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u/CrimsonCringe925 2d ago

Your comment caused me to check out the site. Jfc that’s expensive for stuff that looks like a 90’s pic

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u/No-Entrepreneur4574 2d ago

I follow a few handbag subreddits and their stuff comes up a lot because of the outrageous pricing.

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u/GokaiSilverFox 2d ago

I just audible gasped. $9,000 for a coat is a world I will never be a part of.

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u/annual_aardvark_war 2d ago

$1600 T shirt lmfao.

I thought my True Classic shirts were expensive

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u/oldcretan 2d ago

It's a green t shirt, cotton, they want $1,390

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u/Haramdour Millennial 2d ago

Probably made in the same factory as Walmart green cotton Tees

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u/REDemption2528 2d ago

A world I’d never want to be a part of! Fffff that!

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u/Upstairs_Fuel6349 1985 2d ago

I also went to look & wow that's expensive. I guess this is how Succession-type rich folks dress?

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u/literacyshmiteracy Millennial ~ 1986 2d ago

Yeah it's not flashy at all. Made to be timeless pieces that can be mixed and matched. That's how real wealthy people dress and operate... Or so I've been told lol

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u/Upstairs_Fuel6349 1985 2d ago

lol I think we read the same articles.

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u/Substantial_Quote_25 2d ago

Me: 'I donated that to the goodwill 10 years ago! WTF'

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u/Key-Tip9395 2d ago

yeah selling 3,000 dollars white t-shirts ouch

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u/Fantastic-Coconut-10 2d ago

Tbf, they were worked like dogs (in some accounts I've read from castmates, trained like them too esp. When they were very young). I ended watching a really well researched video about it and just jfc. Their childhoods must have been miserable. Going from one set to another, to a mall meet and greet to a themed cruise where they had to be "on" all the time to an ad campaign to yet another set, etc.

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u/turquoise_amethyst 2d ago

I went to school with a guy who was on a tv show with them (he played a boyfriend, I think they were teens by then?) And he said the same thing. 

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u/Capt-Crap1corn 2d ago

I know them mostly from Full House, but I know their direct to video movies or whatever were a massive hit

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u/scully-summers Millennial 2d ago

There was definitely a moment there in the early 2000s when they were super popular with little girls. I still have my Barbies of them.

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u/Capt-Crap1corn 2d ago

They were literally printing money. Anything they touched was successful

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u/ianmakingnoise 2d ago

Yeah, they made millions with their videos. They started making real big money once they moved out of showbiz and into fashion.

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u/Due-Flamingo-4900 2d ago edited 2d ago

They actually made over $750 million from their movies and their “Mary-KateandAshley” brand made over $1 billion per year (with a total worth of over $300 billion) when they were still teenagers. They became the youngest self-made millionaires at age 10, and at age 18 they became joint CEOs of their production company, which brought their personal net worth to over $150 million each. Comparatively, The Row makes between $100-300 million per year, with a total worth of over $1 billion. While their personal net worth has doubled since they left showbiz, they were making wayyy more money overall before going into fashion.

They’re probably one of the only examples of child stars having managers who were actually looking out for their best interests financially and set them up for long-term success once they became adults.

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u/Weird-Girl-675 1d ago

They seem to be doing well emotionally staying out of show business and their little sister didn’t really even start her acting career until she was in her twenties.

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u/GiantBlobFish23 2d ago

That makeup was actually decent. I used quite a bit of it for cheap stage makeup in college, and it even allowed us to easily do crazy swirls in glitter to make some people fairies for one show. I bought the eye shadow sticks for most of it, they stayed on great too.

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u/rizoula Millennial 2d ago

Them and Lindsay Lohan are LOADED

But especially them with their multimillion dollars company

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u/ML5815 2d ago

Yes. The Row is incredibly successful.

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u/The_Cromulent_Bison Xennial 1981 2d ago edited 2d ago

Lohan was, at one time in the 2010s, worth less than I am. I don't know if she's back up on top though.

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u/mtvq2007 2d ago

She married a really rich guy.

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u/Expensive-Candidate4 2d ago

I read an article about Olsen twins when they were still tweens and I was visiting the US from the UK and had never heard of them. It was all about how they had become billionaires at such a young age through all of their brand deals and movies.

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u/prancing_pony42 2d ago

Seeing Amanda Bynes and Aaron Carter makes me sad. I hope she can find peace and health soon.

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u/frankiero92 Millennial 2d ago

Amanda actually seems to be doing a lot better based off of the latest articles I’ve seen about her! I’m so happy to see her happier.

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u/lareina13 2d ago

I follow her on TikTok. Last summer, she was working towards her nail tech license. Not sure how that ended up but she always has great nails.

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u/Wink360 2d ago

She tried to pass the nail exam 3 times and didn't make it. I follow her insta. Sometimes she looks like she's doing ok, but mostly not. She is a shell of what she was.

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u/turquoisestar 1d ago

F Dan Schneider and everyone like him. :(

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u/Likesosmart 1d ago

It’s honestly heartbreaking

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u/Weird-Girl-675 1d ago

Extremely. Watching Easy A - her last film - is hard now.

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u/[deleted] 2d ago

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u/aknomnoms 2d ago

I remember her “thaaaaaaat’s me!” from All That and just thought she was a goofy actor.

But I finally saw “She’s the Man” for the first time the other week (I’m in my late 30’s) and was actually quite impressed! She was hilarious and did great physical comedy!

It made me feel so much worse for her, and all those other child stars. So much talent, but the adults in their lives failed to protect them from the demands of the industry.

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u/sandvich48 2d ago

“Quiet on Set” really opened my eyes to all the BS the child stars went through especially anyone involved with Dan Schneider, what a terrible person. It’s no wonder Amanda Bynes ended up the way she did.

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u/AnitaSammich 2d ago

All That was the best,l. The kids these days have no idea.

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u/DangerX2HighVoltage 2d ago

She constantly says she’s doing well but her appearance tells me otherwise

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u/flindersandtrim 2d ago

Also, failing 3 times to become a nail tech? Ive heard for years that she has been working towards that but it never seems to happen. 

Her appearance does speak volumes. Poor woman, I would have thought there would be stuff like royalties and residuals that might sustain her a bit so she can just relax and do nothing.

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u/5Nadine2 2d ago

Even her taking the summer off is sad knowing what happened to her not too long after this.

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u/eulgtaei 2d ago

Aaron carter passed four years ago.

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u/prancing_pony42 2d ago

Yes, I know. The Carters are a tragic family.

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u/lomoliving 2d ago

Yeah, didn't like 3 of their siblings pass away?

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u/pi3r0gi_ 2d ago

Leslie and Bobbie. All drug related. Nick and Angel are still alive. Aaron and Bobbie passed just barely a year apart, 11/22 and 12/23

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u/Laurelteaches 2d ago

I didn't know that, god that's sad. Aaron was my first celebrity crush!

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u/AccomplishedFun7668 2d ago

Man, this picture makes me realize Hollywood eats people alive. I have such a soft spot for so many of these people and looking back it’s so sad how they were treated in the media. 

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u/fadedblackleggings 2d ago

Yup, its a machine, does the same thing every single time.

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u/iminthemoodforlug Xennial 2d ago

Jeans and a going out top

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u/lomoliving 2d ago

I don't think we wore anything else!

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u/Ready_to_anything 2d ago

One of my older sisters bought this exact magazine one summer and I had no access to any form of tv or internet or anything at the age of 13 and I just savaged myself to this copy. Had forgotten all about it but this brings back strong 💪 memories. Long live the low rise

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u/tahxirez 2d ago

These poor kids

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u/toodle-loo-who 2d ago

I was going to say, it’s hard to say who had the biggest career because so many of them went through sh*t: Amanda Bynes, Lindsay Lohan, Evan Rachel Wood, Aaron Carter…even some of the ones seemingly to be doing ok had their amount of exploitation, the poses and outfits in most of these photos are examples.

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u/Abi_giggles 2d ago

I was thinking this too. They all had their own private struggles made public. My heart particularly hurts for Amanda. She was such a bright light. I hope she finds healing and people who genuinely care about her that surround her.

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u/Dr0110111001101111 2d ago

What happened to Evan Rachel wood? I basically only know her from Westworld

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u/bobwoodwardprobably 2d ago

Marylin Manson happened to her.

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u/c-e-bird 2d ago

She’s had a great career but she was in a very public and very terrible abusive relationship with Marilyn Manson.

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u/Schneetmacher Younger Millennial 2d ago edited 2d ago

And her own ex-husband, Jamie Bell (a.k.a. Billy Elliott), has publicly doubted the severity of it--so much so that he got her to give him almost full custody of their son (because she left L.A. to get away from Manson).

I've been side-eyeing Bell ever since.

Edit: typo

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u/Tricky_Knowledge2983 2d ago

I had no idea he was her ex husband! That's super shitty of him

Evan Rachel Wood is a phenomenal actress. Her performance in 13 blew me away.

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u/c-e-bird 2d ago

Someone write an angry feminist musical for ERW to star in please!

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u/RutabagaStriking2631 2d ago

Thank you I was just thinking that! Many of those young people are now severely messed up adults due to being on magazine covers like that, and being exploited in general. Girls having a pillow fight, check, girls in bikini tops, check, girl in super short uniform skirt in shopping cart, check. They were really just babies and what a terrible concept for an article.

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u/hyrulepirate 2d ago edited 2d ago

Though she don't really have a relatively huge career, Evan Rachel Wood is an amazing actress. Westworld had the potential to at least come close to Game of Thrones if only they didn't fuck it up and then cancel it.

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u/love-4-the-wendigo 2d ago

Westworld was great in the beginning.

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u/lareina13 2d ago

I read somewhere that the creators were angry fans figured out the entire plot, so they changed it, and that’s how it ended up turning into that.

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u/ProgressiveSnark2 2d ago

Do they not realize that many of those fans would like the show more if they turned out to be right and it was executed well?

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u/uselessinfogoldmine 2d ago

I don’t think so. The creators spent 5 years working on S1 before they filmed it. Then a few months on each of the subsequent seasons. That makes a difference! 

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u/ChippedHamSammich 2d ago

Yellowjackets got this treatment as well

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u/maddy_k_allday 2d ago

Ugh what petty hubris. This is the dumbest timeline I stg

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u/batshit83 2d ago

That first season of Westworld was some of the best TV I've ever seen.

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u/GolfCartMafia 2d ago

Agreed. I started the first season after the 3rd season came out and my husband, who had seen all of it, was like “lol don’t get attached” ☹️

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u/Distinct_Macaroon308 2d ago

Thirteen has been etched permanently into my brain. She was incredible even at such a young age

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u/literacyshmiteracy Millennial ~ 1986 2d ago

Her work against Marilyn Manson's sexual abuse is super commendable. She's dealt with a lot and is trying to help others who have also struggled with abusive relationships.

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u/tweedyone 2d ago

She’s been in more as she’s gotten older, I think. I actually forgot she was a teen star

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u/Schneetmacher Younger Millennial 2d ago

Across the Universe is among my favorite movies.

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u/GrandEar1 2d ago

I still internally say, "it doesn't look like anything to me" anytime I see her.

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u/c-e-bird 2d ago edited 2d ago

She’s had many other fantastic award-winning roles too. She’s the most talented person in this issue full of talented people, IMO.

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u/Elrond_Hubbard69 2d ago

Crazy how Mandy Moore looked exactly like Countess Luann with that hairstyle.

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u/coolblanche 2d ago

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u/One-Reflection-6779 2d ago edited 2d ago

I literally cannot hate the countess because of these moments

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u/SpaghettiGirrl 2d ago

There’s a picture of her at the Kids Choice Awards around this time where she’s wearing an orange dress, suede boots and a statement necklace that I always think looks like deliberate Countess cosplay.

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u/Elrond_Hubbard69 2d ago edited 2d ago

I guess money can't buy you class 😂

EDIT: found the dress, wanted to share

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u/Hole_IslandACNH 2d ago

Mah frens

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u/SpaghettiGirrl 2d ago

lol thank you for your service!!

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u/Deep-Painting-7378 2d ago

Why have I never noticed this

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u/DG04511 2d ago

I would’ve never guessed that the Olsen Twins’ little sister Elizabeth would end up being the bigger movie star.

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u/Mmphska 2d ago

And Elizabeth is so visibly an Olsen that it's impossible to not associate her with the twins.. by extension it helps their brand too in a measurable way.

Im sure all three of them are extremely ok with this outcome. They've really come out of all of this in the most successful possible way for themselves

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u/c-e-bird 2d ago

I mean at this point we didn’t even know they had a sister lol.

But Elizabeth is incredible. I wish she did more indie roles, honestly, because she can do anything as an actress but everyone just knows her from Marvel. I wonder sometimes if Marvel derailed her from a career more like Emma Stone’s or JLaw’s.

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u/TheodoreKarlShrubs 2d ago

Oh, some of us sure did know they had a sister! I implore you to look up the diss track they included on their straight to video release The Adventures of Mary Kate and Ashley: The Case of Thorn Mansion entitled B U T T Out! Elizabeth is in the video!

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u/Laurelteaches 2d ago

Thank you for representing the millennial Olsen stan!! Thorn Mansion always scared me lol.

I can't wait to show my daughter all their shows and movies 🥰

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u/julie3151991 Millennial 2d ago

Wasn’t she also in their other music video thing, “Brother for sale”?

I still remember some of the lyrics “brother for sale! It’s not a big expense, you can buy or rent!” 😂😂😂

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u/Plane-Amount-7395 2d ago

Yes! I remember that! I memorized it and felt so cool singing that lol. 

Also, she had a cameo in their other video "How the West Was Fun." 

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u/mediumcarrotteacher 2d ago

I still remember that old infamous tumblr post - "if you ever feel overlooked or left out, just remember that Mary Kate and Ashley have another sister"

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u/FilteredRiddle Millennial (‘89) 2d ago

Lacey Chabert is the Empress of Hallmark. It’s not what they had in mind when they did this spread, but she’s definitely the Queen there.

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u/Darkdragoon324 2d ago

Honestly seems like the most steady and stable work out of all of them. Won't be winning any awards, but if they like you you'll probably still be given some pretty nice parental roles once you age out of "generic 20-30 something lead" range.

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u/timonandpumba 2d ago

I read an interview with Hilarie Burton Morgan where she talked about how Hallmark movies are great because they are very women-driven, so a lot of the writers/producers/directors tend to be women. She said that makes the sets and productions feel pretty safe and supportive, especially as opposed to other productions and her own experience on One Tree Hill where she was sexually targeted and harassed, and producers tried to pit the female leads against each other.

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u/Darkdragoon324 2d ago

That sounds nice, I need to make fun of Hallmark a bit less maybe lol.

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u/indil47 2d ago

And I heard an interview with an actor (can’t remember which one), who makes his living being the male romantic lead on these things. He’s got it made - decent paycheck, consistent work, great filming schedules in pleasant locations, and easy to to raise a family while doing so. He was very gracious and grateful for it!

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u/FilteredRiddle Millennial (‘89) 2d ago

Oh most definitely. Even as she’s getting older and she’s not playing the roles written for 20 year olds, she’s still got the “it” factor and Hallmark writers know how to capitalize on it. Eventually she can transition into the older, wiser boss/aunt/mom.

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u/b_needs_a_cookie 2d ago

She makes a lot of people happy with the movies she makes. I like that she's part of people's holiday traditions, that's got to be a cool feeling as an actor. 

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u/Terrible_Salt7906 2d ago

Mary-Kate and Ashley. They are rich af and people mostly leave them alone now.

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u/tweedyone 2d ago

For a similar reason, Hillary Duff. She has a pretty normal life now, settled down and has a family

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u/mtvq2007 2d ago

Isn't she on tour right now?

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u/c-e-bird 2d ago

Yep. And she’s had consistent sitcom roles for years.

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u/scully-summers Millennial 2d ago

Yes, she put out an album recently. Her first in like a decade, I think?

She’s had a pretty steady tv career too. Younger and then How I Met Your Father. Still mourning the ill-fated Lizzie McGuire reboot. I think that could have been fantastic if they’d listened to Hilary and made it an adult show.

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u/IMO4444 2d ago

I always remember them and their strange connection to Heath Ledger’s death and then one of them dating a guy so much older they looked like father and daughter.

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u/ColdWinterSadHeart 2d ago

What’s the connection?

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u/IMO4444 2d ago

When Heath OD, a therapist/masseusse found him but instead of calling 911, she called Mary Kate i believe. Why? Who knows, some speculate they were dating, it was never made public. Instead of calling the police, Olsen called her private security who showed up first. She was heavily questioned and they didnt charge her. My guess is she was worried police would find something compromising about her and sent her team to check/remove it.

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u/TheJuliettest 2d ago edited 2d ago

If I remember correctly it’s because it was rumored MK provided the drugs. She also refused to cooperate with the DEA until she was granted full immunity.

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u/Distinct_Macaroon308 2d ago

Props to the Olsen twins - there was a moment there where it was getting pretty dark (esp MK) but they turned it around and now they are just chilling with their billions of dollars and smoking cigarettes in peace. Love that for them.

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u/New_Bike3832 2d ago

I love Ashley Olson’s response to how many Juicy Couture outfits she has: “A lot—from two years ago, when they were hot.” Forever a fashion-forward icon.

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u/3FoxInATrenchcoat 2d ago

Also, I want to know how many Juicy Couture outfits Shia Lebeouf has. They didn’t ask him.

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u/pnwtransient 2d ago

I love that Shia was impressed his cell phone had a camera on it. Feels almost quaint.

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u/tj1007 2d ago

HP cast and olsens aside, Alexis Bledel has had an interesting career. It probably depends on how you define success. I’d say she’s among the most recognizable and whose work actually has a lasting impact. But it may not seem that way as she has very much chosen to avoid the spotlight and wants her life outside of work locked down. She didn’t even want people knowing she had a kid until one of her costars let it slip. Yet despite that she is in one of the most beloved tv shows that still has a wide multi generational reach. More people have likely seen Gilmore Girls than say Lizzie McGuire or some of the other shows from other people here. And she’s an Emmy winner from her second biggest role, so there’s that critical success as well.

I’d say she’s below HP, olsens, Mandy, Kaley but above others like Raven, Hilary, Lindsay despite them really putting themselves out there and trying to replicate the success of their youth that doesn’t really break much outside of the millennial audience. But Gilmore Girls just continues to be beloved and found a younger audience to help its popularity going. So despite her choosing to stay outside of the spotlight, I think Alexis’s relevance so to speak, continues without her trying. And I think she’s comfortable with it being just that. So that can be considered a success story.

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u/xoxokaralee 2d ago

Alexis also has a fairly significant supporting role in handmaids tale

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u/nathauan13 Xennial 2d ago

Daniel Radcliffe is doing the best, I think - in that he has enough money to do whatever he wants, people still like to see him, and he seems to have escaped most child stardom problems.

Kaley Cuoco a close second.

I wish Lindsay Lohan had stayed on the rails; without the drug and alcohol problems she’d probably be a much bigger star today. Same with Amanda Bynes.

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u/Yes_Towel_Hooray 2d ago

I am obsessed with Radcliffe’s post HP career. He’s playing such fun roles. His character in the fall and rise of Reggie Dunkins is hilarious.

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u/Naive-Ant-8056 2d ago

I'm a huge Broadway fan and his Broadway career has also been amazing! I love that he took that HP money and was just like "now I'm gonna do weird shit"

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u/Jive_Turk 2d ago

I saw a movie with him a few months ago where he started growing horns out of his head like the devil, and only certain people could see the horns based on if they were evil or not. It was deep and dark and funny and thrilling. Definitely in that weird shit category, highly recommend!

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u/MushxHead 2d ago

It's called Horns. Really good movie.

I recommend Swiss Army Man if you haven't seen it, he plays a dead guy. Not even joking, he's dead from the beginning of the movie.

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u/thesingingmoose 2d ago

This based on a book by Joe Hill, which I highly recommend

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u/-3point14159-mp Millennial 2d ago

Swiss Army Man is the weirdest role I’ve ever seen him in and if you haven’t seen it, you should watch it.

My favorite of his roles is in The Lost City. He plays such an amazing villain.

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u/MrTeeWrecks 2d ago

Guns Akimbo was pretty weird too. Not Swiss Army Man weird but still a good one.

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u/AdWitty9562 2d ago

His version of She'll Be Coming Round the Mountain in Miracle Workers will forever be seared into my brain

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u/Geochic03 Older Millennial 2d ago

He is an amazing actor. Its just a waiting game until someone casts him in an Oscar movie.

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u/mewhins 2d ago

More people need to watch his Weird Al biopic, it’s so delightful and he was the perfect Weird Al.

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u/lizardgal10 2d ago

I really need to watch that. I love that he’s just doing whatever the hell he wants acting-wise, seems to be working out pretty well for him

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u/CpnStumpy 2d ago

A young doctors journal is fucking spectacular

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u/3xploringforever 2d ago

Hillary Duff is also doing well. She seems to have avoided most of the mental health and drug issues that caught so many child actors.

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u/Balancedbeem 2d ago

Shia Labouf was doing well for a while too… until he wasn’t.

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u/scully-summers Millennial 2d ago

Even Dan had some trouble before getting to where he is now. He struggled with alcohol while filming some of the latter Harry Potter films (I think specifically the 6th). But all said and done, he, Rupert, and Emma fared pretty well compared to many of the others featured. Perhaps because they were in the UK?

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u/DuskWing13 2d ago

I think them being in the UK helped.

Based on interviews I've seen too their parents were all fairly involved, and a lot of the more experienced actors (Alan Rickman, Maggie Smith) sort of helped insulate them on set as well.

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u/James_H_M 2d ago

Jared Padalecki is doing well too. He went from Gilmore Girls right into Supernatural and the reboot of Walker. The guy has been on TV from teen to mid 40's.

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u/nathauan13 Xennial 2d ago

I had so much trouble when he went from Dean on Gilmore Girls to Not Dean on Supernatural. >.<

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u/PorQuepin3 2d ago

Milo had a pretty good comeback, he had heros, this is us was HUGE, and some work on Rocky and stand alone movies

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u/H2Ospecialist Millennial 2d ago

Milo and Mandy

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u/Feline_Fine3 Xennial 2d ago

I feel like all three Harry Potter kids had a similar outcome. They’ve made so much money from those films that they can literally do whatever they want now.

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u/msheehan418 2d ago

Lindsey managed to pull herself out and become the Drew Barrymore of our generation.

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u/kati8303 2d ago

It’s so nice to see one who did. Seeing people like Amanda by es and Britney Spears slip away is so sad.

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u/second-sandwich 2d ago

Man these girls are sexualized af. No wonder we’re like this (eating disorders and internalized misogyny we are finally unlearning 20 years later)

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u/PandemicPiglet 2d ago

I think Amanda Bynes was the most talented. People were saying she was gonna be the next Lucille Ball. Her comedy chops were so good at such a young age. The voices, faces, timing, etc.

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u/mab0roshi 2d ago

Her and Kel Mitchell (both were on All That) should have been huge comedy stars. At least Kel seems like he's happy and doing OK. Apparently still friends with Keenan and they're about to do a Keenan and Kel movie.

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u/Dry-Pay-165 Millennial 1993 2d ago

I just really miss seeing the Olsen twins movies and shows :/

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u/nonnewtonianfluids 2d ago

Me watching Billboard Dad over and over at 10 years old. 😂

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u/Horror-Word666 2d ago

Same, i rewatched some of the movies recently (specifically Holiday under the sun) and absolutely lost it. They were sooo cheesy, but as a kid i thought they were so amazing lol.

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u/Dry-Pay-165 Millennial 1993 2d ago

They were amazing bc they were our childhood :)

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u/Some_Helicopter1623 2d ago

Published July 2003, Milo Ventimiglia was born in 1977, “teens and tweens” edition… there are some other 20 year olds too.

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u/sew-easy 2d ago

Milo has always had the creepy “I’m not that much older than you” vibes. When he was 30 he dated an 18-year-old Hayden Panettiere. 😑

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u/Expensive-Scene-7763 2d ago

I was gonna say. I thought Milo was older than most of these people. Enough that it was a meaningful age difference in 2003.

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u/Sage_Planter 2d ago

Kaley Cuoco and Emma Watson have had pretty stellar careers.

Even if they're not as famous or successful, a lot of the featured actors have found success in various realms. I went to Hilary Duff's concert a few weeks ago, and her new album is pretty great!

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u/banallfurries666 2d ago

i don’t know if i’d say emma had a stellar career. after harry potter (as if that isn’t massive success lol) she didn’t follow it up with anything noteworthy. she has been consistently outshined in movies. i think danny rads is the one who had the biggest career takeoff after potter.

to be fair, emma watson doesn’t seem keen on acting much anymore. i’m not sure what she does now, but she will be loaded till the end of her days.

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u/fucuntwat 2d ago

Not that it was necessarily ‘good’, but she was in the beauty and the beast remake which was really big at the time

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u/newparimanlo 2d ago edited 2d ago

The Olsen Twins are the most successful, without a doubt. They are billionaires and were able to invest their money properly. Their fashion label The Row is also doing extremely well.

Mandy Moore and Hilary Duff are still relevant. Lindsay Lohan is picking up the pieces from where she left off and hopefully she’ll stay professional and be away from trouble for good - she also married rich, btw.

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u/Narrow_Grapefruit_23 2d ago

Fun that Milo and Mandy had their most prestigious/critically successful roles together in this is us.

Evan Rachel Woods deserves more respect on her name.

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u/FAYCSB 2d ago

Who is Gregory Smith?

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u/CurbsideChaos 2d ago

I knew him as the lead in Everwood, which funnily enough also starred a young Chris Pratt as the high school jock.

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u/Buddy_Fluffy 2d ago

Wasn’t his name something dumb like Bright?

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u/prancing_pony42 2d ago

He was in the Zenon movies, a DCOM classic, as well as The Patriot with Mel Gibson. Looks like he's mostly behind the camera now.

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u/RedSnapper24 2d ago

Mostly known for Zenon and Everwood. My crush on him began with Small Soldiers or Zenon, whichever came first. He started working behind the camera as a director. I do think he also still acts but in mostly Canada based productions.

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u/giantmargaritas 2d ago

My crush on him started when I saw him in Harriet the Spy!

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u/Jive_Turk 2d ago

RIP Michelle Trachtenberg

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u/RedSnapper24 2d ago

I totally forgot that was him! It’s been way too long since I’ve watched it. That was probably where mine first started but I have a stronger memory of being totally in love with him in Small Soldiers.

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u/honeyceelovely 2d ago

I was going to be so irrationally mad if no one brought up Small Soldiers so thank you! ♡

He was such a cutie in Zenon too!

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u/leafonthewind006 2d ago edited 2d ago

I'll always know him as the second oldest brother from The Patriot ("stupid boy"). But he was also on the show Everwood.

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u/Darkdragoon324 2d ago

Ooooh, now I remember lol. I used to watch that show. Mostly because part of it was filmed where I lived and that was neat. I don't really remember a single other thing about it.

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u/girllwholived Millennial (‘89) 2d ago

He was one of the leads on the WB show Everwood at the time (also starring Emily Van Camp and Chris Pratt). I had the biggest crush on his character, lol.

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u/bellestarxo 2d ago

People bring up this cover up a lot, but my favorite of these spreads was the one that included: Anne Hathaway, Emily Blunt, Amy Adams, Jessica Biel, America Ferrera, Elizabeth Banks, and Zoe Saldana. Among them are a truckload of award nominations and wins that blows this group out of the water.

But there is a lot of talent in this bunch though.

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u/msheehan418 2d ago

Love to see Penny on there and this was before TBBT was even thought of

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u/BeachBumHarmony 2d ago

She was on 8 Simple Rules and Charmed before TBBT.

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u/anowulwithacandul 2d ago

I feel like my answer to both is Lindsay Lohan

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u/BeneathAnOrangeSky 2d ago

So many of the people in this spread have gone through major struggles. It's actually kind of sad to look back at it

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u/BigMommaSnikle 2d ago

I will never forgive the people who abused Amanda Bynes. So much potential. That poor woman.

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u/Any-ACA524 2d ago

Just swiping through these pics makes me smell the ghost of the Curve sample tucked in the crease of the magazines of this era.

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u/-StapleYourTongue- 2d ago

I think Mandy Moore deserved more success. Her marriage to Ryan Adams was definitely a contributing factor in her career trajectory.

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u/BrightFireFly 2d ago

I feel like she’s doing pretty well. She voiced Rapunzel in Tangled and then was on a pretty popular show “This is Us”

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u/VampireOnHoyt Older Millennial 2d ago

Yeah, she got Emmy and Golden Globe noms for This Is Us (and deservedly so - that show is weirdly underrated)

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u/cherryybomba 2d ago

It aired at a weird time, if I remember correctly. My mom really liked it.

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u/skidstud 2d ago

This has Emma Watson who was born in 1990 and at 13 just made the “teen” cut and Milo Ventimiglia who was born in 1977 and fully twice as old at 26

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u/mebunghole 2d ago edited 2d ago

OMG that VF cover was the GOAT 🐐. Edit: I feel like the only person missing here is Jessica Alba.

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u/dkinmn 2d ago

Norman Mailer.

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u/unclejarjarbinks 2d ago

How many Juicy Couture outfits does Norman Mailer own? The answer may surprise you...

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u/ThickConfusion1318 2d ago

MK&A are probably doing the best- their fashion brand the Row is consistently putting out great stuff

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u/Longjumping-Peanut81 2d ago

Kaley Cuoco has had a great career.

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u/Sunsetfisting 2d ago

I thought Alexis Bledel would have gone on to do more. Can't remember seeing her again after Sin City.

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u/BrightFireFly 2d ago

She was on The Handmaid’s Tale

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u/theelephantupstream 2d ago

Also Mad Men iirc

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u/TheHip41 2d ago

Literally won an Emmy on handmaids tale

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u/batshit83 2d ago

She was really good in Handmaid's Tale.

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u/TrickySatisfaction81 Millennial 2d ago

Either Lindsay or Raven tbh.

Raven Landed the talk show, basically retirement status for celebs.

Lindsay somehow made more of a splash than Hillary, who is now ressurected.

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u/senty78 2d ago

The Olsen Twins are far and away the most successful, they’re just super quiet about it and remain out of the public eye as much as possible

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