Image Credit: Getty Images

These Celeb Moments From The 2000s Keep Me Up At Night

There are moments that define us. To some, this might be walking across a stage in your cap and gown and swinging your tassel proudly, waving over to Grandma Jean, and rolling your eyes as your mom sobs into a hanky. To me, it’s knowing exactly where I was when I heard the news about Jennifer Aniston and Brad Pitt. That divorce has caused me more emotional damage than any of my own breakups.

It’s just one of the many celeb moments from the 2000s that will keep me awake at night. Instead of dozing off to sleep, I’ll see a montage of glossy magazine headlines and worst-dressed lists. I’ll recall the sexual awakening of that one MTV kiss, and the fear that ran through me when Tyra dropped to the ground.

Here are the life-changing Y2K celeb moments that I can’t forget, no matter how hard I try or how much valium I take.

1. Tom Cruise Being Outed As A Scientologist

Image Credit: Getty Images

I didn’t even know what a Scientologist was, and I’ll be honest, I’m still not really sure. It sounds like they’d be rational and prioritize science over other things, but I’m guessing that is FAR from the truth.

I can clearly recall the shock of discovering that Tom Cruise was this mysterious thing. This was before the time of the Illuminati, so it was the closest to secret conspiracy groups that we had going for us. 

This also coincided with his deteriorating marriage to Katie Holmes, whom I adored. Their daughter, Suri, was also always dragged into things, and I lapped up any info I could find with gusto. I remember papers being appalled at the expensive clothing Suri was dressed in, but they were like millionaires, I’m guessing, so what are they going to put her in? Forever21? Let’s be real, guys.

2. Mr. And Mrs. Aniston Smith

Image Credit: Getty Images

It wasn’t my parent’s divorce that broke my belief in true love, it was discovering that Brad Pitt had cheated on Jennifer Aniston. I was a total Jennifer girl, and before you ask, yes, I’d be a Rachel, not a Monica.

How could Brad cheat on someone as perfect as Rachel? It truly showed me that no matter how incredible you are, men can still be pigs. 

Angelina Jolie and Brad Pitt got together while filming Mr. and Mrs. Smith, and it was news that rocked the nation.

Unfortunately, we did the awful thing of blaming the other woman, and Angelina became a punching bag for everyone’s fury. She was seen as a seductress compared to Jennifer’s Girl Next Door. Angelina, I’d like to apologize on behalf of all of us for fueling too much blame at you, and not enough to that scumbag who was actually married. 

3. When Piers And Paris Got Married

Speaking of marriages, I feel like we’ve all collectively blocked out the fact that Piers Morgan and Paris Hilton casually got married.

In 2010, the duo got married in Vegas for a TV show, with Frank Sinatra, Elvis and Marilyn Monroe in attendance. She wore a gown and veil, brought one of her infinite little dogs, they exchanged rings, and Piers even got a little smooch out of it. Following the nuptials, the pair celebrated at Planet Hollywood, which likely beats some of the wedding buffets I’ve had this summer.

Both of them are now remarried, so it seems like it wasn’t a legally binding wedding, but I’m still so confused. Namely, just… why? Also, Queen Paris should not be associated with Piers Morgan in any way and I hate him knowing he’s kissed her. UGH.

4. The Beyoncé Stampede

Image Credit: Getty Images

This feels like a weird fever dream, and I had to do a lot of searching to discover if I had actually just made this up. But no, it’s true, there was a literal Beyoncé stampede.

In 2003, Beyoncé posed with 50 lookalikes in Vegas. It literally looks like someone copy and pasted a dozen times. I feel like I’m staring at some kind of optical illusion.

Why did they do this? Did they buy everyone that outfit to ensure they’d all be matching? Why the little yellow kitten heels? I need to know more. 

5. Orange Is The New Martha Stewart

Image Credit: Getty Images

Way before Orange is the New Black graced our screens with sapphic sex scenes and prison riots galore, we were introduced to the prison system when Martha Stewart got sentenced to five months in prison on charges of conspiracy, obstruction of justice, and securities fraud. Big words that basically mean she did some insider trading when she was tipped off to sell shares before they’d lose value. Kind of girlboss, I guess?

Until then, Martha had been known as the ultimate homemaker and baker, so this was confusing, to say the least. Martha did her time peacefully and even earned the nickname of M. Diddy from fellow inmates. She was released in 2005, and then placed in home confinement for five months, and another year and a half of supervised release. She made quite the comeback, returning to her company, Martha Stewart Living, and even appearing in an adapted version of The Apprentice. Also she is now besties with Snoop Dogg??

6. That MTV Kiss

It was 2003 and I was watching the MTV Video Music Awards. Madonna, Christina Aguilera, and Britney Spears performed a medley together, and finished it off by kissing one another. I couldn’t tear my eyes away, I felt all the breath leave my body, and I levitated to a new plain of sexual awakening. When I stood up to switch off the TV, having been called to set the table for dinner, I was no longer a girl, but a woman now.

This kiss has been discussed, deconstructed, and debated by scholars and girlies alike. It was a kiss that changed lives. Apparently, it was a last-minute decision to add the kiss, and thank god that Madonna had this epiphany. This moment was a true win for the girlies.

7. Every “Got Milk” Ad

You couldn’t turn a street corner or open a copy of Cosmopolitan without seeing a “Got Milk?”  ad. I’m still so confused by what these ads were trying to sell. Was it literally just milk? Were they a milk brand? Were they government-assigned to force us to drink more milk and try to drive away the impending takeover of oat milk?

These ads would never fly nowadays. I’m genuinely curious how many people actually bought milk after seeing these.

Countless celebs were featured in these “Got Milk?” ads with the telltale milk mustache, including: the Spy Kids, Beyoncé, Billy Ray Cyrus, Kermit the Frog, Kate Moss (naked of course), Amanda Bynes, Angelina Jolie, Steven Tyler, Lindsay Lohan and ex-con herself, Martha Stewart/ M. Diddy.

They had a mad budget apparently. I’m still not convinced this wasn’t some other conspiracy or brainwashing campaign, it’s just all too strange.

8. Every Episode Of My New BFF

As a celebrity, it can be hard to make new friends. I can relate, as a Betches regular who recently hit 550 followers on Instagram. You just don’t know who you can trust, who is friends with you for the right reasons, and what will get leaked to the press.

The solution? To make a reality TV show where contestants compete to be your new best friend forever. In Paris Hilton’s My New BFF, contestants had to prove they had what it takes to keep up with the iconic heiress. They had to party for the longest, swear they’d die for her, get makeovers, learn to pose for paparazzi, and so much more.

Shockingly, this show only ran for two seasons. Even more surprising is that when season 2 aired the season after, Paris stated that she and season 1’s winner, Brittany Flickinger, were no longer besties!! What? I genuinely thought they’d be friends for life.  

9. Winona Forgetting To Pay

Image Credit: Getty Images

In 2001, Winona Ryder (known as the main crazy one in Girl, Interrupted) was arrested for shoplifting over $5,000 of designer clothes and accessories from a Beverly Hills Saks Fifth Avenue. This might seem like a rather trivial occurrence, as if we’re honest, many of us went through a case of sticky fingers as a teenager. Only the lipgloss we swiped from Claire’s was more likely to cost $5 than $5,000. 

But the public was outraged by this. They would not accept that this girlie was doing some post-production method acting and going off the rails for a slight moment. She was convicted of grand theft and shoplifting. I’m guessing the closest Winona had gotten to grand theft before this was sleeping with a guy and then watching him play GTA.

She did her community hours and apologized frequently. She claimed this was a difficult time of her life and she’d been on a lot of medications that in hindsight shouldn’t have been prescribed to her. Bestie, we get it, turning 30 can be difficult and we’re all just trying to find our slay way.

10. The Love Triangle That Defined Love Triangles

While adult drama was fun, nothing was more thrilling than teenage celebrity drama. We were literally watching them grow up before our eyes and we couldn’t wait to offer our opinions.

America’s Sweetheart Hilary Duff was a household favorite. She met Aaron Carter on the set of Lizzie McGuire, when he was featured in a Christmas episode. They started dating but two years later, he cheated on her with Lindsay Lohan! Yeah, the one from Freaky Friday!

Gasps all around as the two Disney princesses had been friends until that point.

The young lovers tried to make it work after that, but soon broke up for good. This short relationship was outlived by the feud that continued between Lindsay and Hilary, which would go on for years to come. It included Lindsay mocking Hilary on SNL, Hilary writing thinly veiled songs about the betrayal, and Lindsay shit-talking Hilary to Chad Michael Murray. (Yeah, he’s somehow involved in this too.) 

11. Tyra Fainting on ANTM

Decades from now, scholars will still be constructing the bizarre behavior of Tyra Banks on America’s Next Top Model. A reality show that supposedly aimed to find the next new hit of the modeling world (although many winners have since admitted they had no opportunities after the show), it was more like an hour-long episode of THE TYRA SHOW. 

It featured Tyra telling STUNNING WOMEN how unattractive they were, everything they were doing wrong, that they were hurting HER feelings, that they were unprofessional, and so much more.

Tyra was certainly one for theatrics. From her iconic meltdown of WE WERE ALL ROOTING FOR YOU!!! to her coining the phrase POT LEDOM. But the real jaw-dropping moment was in cycle six (cycles not seasons!) when Tyra pretends to faint in front of the models. They all begin panicking and one even starts crying, and then Tyra jumps up and yells in their faces. All to announce that this week’s challenge would be… acting. To this day, I am scarred by that moment.

12. Hilary Duff on Gossip Girl

Image Credit: Getty Images

We’re going to round it off with a celeb incident that’s a little late for the 2000s but so iconic that I had to include it: Hilary Duff’s stint on Gossip Girl.

By season 3, the show was already a big hit, and the already-known cast had become big news. So I’m not sure why they felt the need to bring in Hilary Duff. She played Olivia Burke, a famous actress going to NYU and dating Dan Humphrey. Some people think it was a reference to Emma Watson going to Brown University but IDK, people like Emma too much to make this storyline apply to her.

There are many bones to pick with this character and her storyline. Her supposed role in a vampire series, where their sex scenes cause them to levitate (Twilight could never). Her involvement in the modern Snow White adaptation where they sing Lady Gaga songs (Sorry WHAT?). But I’ll focus on the one I have tried consistently to forget: her threesome with Dan and Vanessa. 

WHY DID THIS HAPPEN? It was hard enough to believe Dan could pull Serena, but now he has a threesome with a literal famous actress? It felt as awkward as preteens playing “7 Minutes in Heaven.” I have nightmares about their slow kisses and smirks. I wish I could forget it. I guess she really did play a “Love Game.” 


Fleurine Tideman
Fleurine Tideman
Fleurine Tideman, a European-based copywriter. She’s interesting (cause she’s from Europe), speaks multiple languages (again, she's from Europe), and is mentally unhinged (despite socialized healthcare). You can find her European musings on Twitter @ByFleurine and her blog, Symptoms of Living, both of which are written to the sounds of unhinged Taylor Swift playlists.