Sandra Bullock and Keanu Reeves
Why does Sandra look vaguely like a fancy pirate? These two must have been promoting The Lake House, a.k.a. the Magic Mailbox movie, a.k.a. arguably my favorite of my husband's wacko Halloween costumes (he went as the mailbox)(and told his friends he was going to do it, so then one of them showed up as the OTHER mailbox, with a letter in it from future Kevin apologizing to this friend for stealing HIS costume... listen, that is a lot to summarize, but as gags go it was a real home run that night).
Rihanna
Ah, young Rihanna, dressed like a kid at her school dance. Still luminous.
Jessica Simpson
This ALSO feels like it's playing to the teen dance crowd.
Reese
A surprise belt from Reese! It does help the outfit to have a pop of color there.
Kristen Bell
She could wear this entire thing now and be fine.
Dax Shephrd
He and KB were not married yet. I don't know what he was doing here, besides being The Most.
Jared Padalecki
Well. First, this hair is going to make a huge comeback among dudes who don't want anyone taking clippers to their hair in quarantine. Second, I do not think his shirt has been washed in months. Third, you're not at the beach, kid.
Ming-Na Wen
Teens were hopefully not choosing shorts jumpsuits with giant cummerbunds, no matter what Ming-Na decided.
Tichina Arnold
I mean... either it's going to be a tank top, or it's going to be Baby's dress from the Dirty Dancing finale, but it cannot be both.
Wilmer Valderrama
Sure.
Kevin Federlin
He actually cleaned up okay for this! With today's better jeans for men, this might even look slick.
Britney
They had pregnant Britney come out to introduce him. I forgot she'd gone brunette here. Also, I don't know WHAT the hell has happened with this microphone stand, and a bra lazily dangling from its boobs. But... you know, Fox used to fancy itself as MTV-edgy, I think. It was not.
Ashton Kutcher
Is that a Che Guevara belt buckle? I suppose we're lucky he wasn't in an Ed Hardy trucker hat.
Hilarie Burton
OTH's Peyton Sawyer looks very cute.
Sophia Bush
And so does OTH's Brooke Davis. Little did they know that K-Fed would one day soon be their colleague, playing the role of... wait for it... J-Fed.
Ashley Olsen
"J-Fed? You're shitting me, right?"
Nelly Furtado
Snazzy!
Orlando Bloom
Decidedly NOT snazzy. Come on, dude.
Jessica Alba
"I could be a glamorous pirate in a sequel, Orlando! Just say the word! Love, Jessica Arrrrrrrba HAHA SEE?!"
The Jonai
Nick is a FETUS in this photo. And I sincerely fell for Joe's shirt and thought he had a robot hand.
Emily Deschanel
That is some shockingly tall hair on Temperance Brennan.
Zooey Deschanel
Whereas there is nothing surprising here at all.
Rachel Bilson
This is... I assume it was MEANT to have the camisole, and that she didn't just add it to give herself coverage. But I would BELIEVE that excuse.
Mischa Barton
She looks so cute. MEMORIES.
Mischa Barton
This has a hearty dose of clown DNA but it's still not bad at all.
Miley Cyrus
You didn't NEED the pants, Miley.
Paula Abdul
These pants are so high-waisted, they're actually also her underwire.
Haley Bennett
She seems so excited. This is before her film debut Music and Lyrics (which was in 2007), so she was probably THRILLED to be on a red carpet and also weirded out that maybe nobody knew who she was.
The High School Musical Cast: Lucas Grabeel, Monique Coleman, Corbin Bleu, Ashley Tisdale, Zac Efron and Vanessa Hudgens
And these kids! They were the biggest thing going, and I think only Zac Efron currently has the same level of professional visibility, with Vanessa Hudgens close behind.
Zefron
She's The Man came out in 2006, and he reminds me SO MUCH of how they styled Amanda Bynes when she was pretending to be her own brother. I've decided they had a Zac Efron Mood Board when they were making that movie.