1 | Angelina Jolie and Billy Bob Thornton piled on the PDA.

This was the year that Angelina Jolie and Billy Bob Thornton—two actors with an age gap as wide as the time that's passed since this photo was taken—got married, not long after Thornton broke off his engagement with Laura Dern. Their romance was brief, only lasting till 2002, but it was also entertaining and totally chaotic. The stars famously wore vials of each other's blood, and Jolie's tribute tattoo is on display in this snap from the premiere of her film, Gone in 60 Seconds. For more on that Dern and Jolie overlap, here are 60 Celebrities Who Share an Ex.

2 | Destiny's Child were still a foursome.

When they walked (and matched) the red carpet at the 2000 Soul Train Awards, there were four members of the girl group Destiny's Child. Not the four original members, as Michelle Williams and Farrah Franklin (the two women on the left) were brought in this very year to replace LaTavia Roberson and LeToya Luckett. Franklin departed the group just a few months after this awards show, leaving Williams and original members Kelly Rowland and Beyoncé to continue on as a trio.

3 | Julia Roberts and Benjamin Bratt were an "it" couple.

America's Sweetheart Julia Roberts and Law & Order star Benjamin Bratt were the object of a great deal of envy for the four years that they were together. They set off flashbulbs everywhere they went, including the premiere of 2000's Red Planet, but it came to an end in 2001. Both actors have said that their split was amiable and still seem to hold each other in high esteem. For stars who are expanding their families this summer, here are 15 Celebrities Who've Had Babies During the Pandemic.

4 | Denise Richards embraced big hair.

"The higher the hair, the closer to God," some say. And in the year 2000, future Real Housewife Denise Richards seemed to subscribe to that belief. Then best known for her roles in Wild Things and The World Is Not Enough, the actor went for a teased-up coif and frosty eyeshadow at the MTV Movie Awards.

5 | Matthew McConaughey shaved it all off.

From old-school country singer hair to a cue-ball look, here's Matthew McConaughey at the premiere of What Women Want. He's shaved his head a couple of times, including for a role, but it seems like this visit to the barber was for a different reason. Per HuffPost, McConaughey revealed in a talk show appearance that his hair had started thinning in 1999 and credited a hair growth serum for bringing it back thicker and healthier. Worried about your own strands? Here are The 10 Biggest Myths About Hair Loss You Need to Stop Believing.

6 | Will Smith caressed Jada's baby bump.

Call this one of Willow Smith's first red carpets. The singer's parents Will and Jada Pinkett Smith brought her along—in bump form—to an Oscar De La Hoya and Shane Mosley fight.

7 | Ted Danson cosplays the Cat in the Hat.

Ted Danson showed up for the premiere of Dr. Seuss' How The Grinch Stole Christmas in the guise of another of the children's book writer's famous characters. And somehow he still looks suave. For stars who've made up their own monikers, here are 50 Celebrities Whose Real Names You Never Knew.

8 | Serena Williams and Venus Williams were all smiles.

Then 18 and 20, tennis phenoms Serena and Venus Williams were pretty in pink on the red carpet of the Teen Choice Awards.

9 | Jodie Foster and Russell Crowe went on a date to the Golden Globes.

Did you know Oscar winners Jodie Foster and Russell Crowe dated? Let this photo of them hand-in-hand at the 2000 Golden Globes ceremony refresh your memory. And for more celeb surprises, sign up for our daily newsletter.

10 | Nobody's Angel coordinated their look.

Sure, you remember the Spice Girls and the Pussycat Dolls, but the 2000s bred many pop girl groups who may be less familiar to you, 20 years on. In 2000, the ladies who went by the name Nobody's Angel walked the carpet at the American Music Awards, looking extremely shiny.

11 | Elisabeth Moss was totally fresh-faced.

Now, she's recognized as one of the most formidable actors of her generation. But in 2000, Elisabeth Moss was just getting started. When she was also known for playing the president's daughter on The West Wing, Moss attended the premiere of her movie Girl, Interrupted in a timeless denim jacket.

12 | Tracee Ellis and Rhonda Ross proved it's all in the family.

The multitalented daughters of Diana Ross—future black-ish star Tracee Ellis Ross and Another World actress Rhonda Ross—stayed close when they walked the carpet at the 2000 NAACP Image Awards.

13 | Three-fifths of *N Sync gave Ananda Lewis a boost.

If this photo doesn't get you in your TRL feelings, nothing will. Backstage at the TCAs, boy banders Justin Timberlake, Chris Kirkpatrick, and JC Chasez goofed around with MTV VJ Ananda Lewis.

14 | Linda Cardellini and Jason Segel were adorably in love.

Back in 2000, future Dead to Me star Linda Cardellini and her Freaks & Geeks costar Jason Segel, who'd later play Marshall on How I Met Your Mother, were an item. Despite looking cozy at the premiere of The Contender, it was not to be. Rumor has it that their breakup partially inspired Segel's rom-com Forgetting Sarah Marshall.

15 | Anne Heche, Sharon Stone, and Cher served looks.

Three women who'd never choose to fade into the background, Anne Heche, Sharon Stone, and Cher brought a fetching combination of leather, sparkles, and tiny sunglasses to the Women in Film Lucy Awards.

16 | Spinal Tap reunited.

Michael McKean, Harry Shearer, and Christopher Guest suited up as their faux rock band Spinal Tap for the 2000 red carpet celebration of the 1984 rockumentary This Is Spinal Tap being released on DVD.

17 | Jet Li and Aaliyah were proud costars.

Late pop star Aaliyah and her Romeo Must Die costar Jet Li looked as pleased as can be at the premiere of their romantic action flick.

18 | Hanson had great hair.

Taylor, Zac, and Isaac Hanson (of the ubiquitous '90s hit "Mmmbop") brought their brother act to the TCAs. They delivered in smolder—and hopefully, some haircare tips.

19 | The Osbournes were a package deal.

Metal icon Ozzy Osbourne brought the whole clan to the 2000 Grammys, including wife Sharon and their kids, Jack, Jessica, Aimee, and Kelly. Their outing may have gotten some producers talking, as two years later, their hit reality show The Osbournes would make its debut.

20 | Drew Barrymore and Tom Green were blissfully happy.

Fans were shocked when MTV goofball Tom Green and in-demand actress Drew Barrymore fell for each other, but so they did. They got married in 2001, not long after this date to the premiere of Charlie's Angels, in which Barrymore stars and Green had a cameo. Five months later, the whirlwind romance was over—but at least everyone had fun while it lasted.

21 | 112 made the case for matching suits.

Matching outfits have mostly fallen out of favor for pop groups, but look at R&B singers 112 at the Arista Records 25th anniversary party! They're making it look good.

22 | Beth Broderick cuddled Salem.

Salem (or a real stand-in for the show's animatronic cat) does not look particularly thrilled to be posing for photos with Sabrina the Teenage Witch actress Beth Broderick at a 2000 promo event. We can only wonder what the verbal version of Salem would have to say about it.

23 | P!nk just went for it.

The '00s were a time for experimentation, as evidenced by the fact that many of these style choices haven't been repeated. But you have to give P!nk props for having the guts to pair this cash-print top with a multi-colored glittery 'do at the 2000 Billboard Music Awards.