Sean Penn and Madonna met in the winter of 1985 and married soon after, in August of the same year. That’s a good way to make one year the best in less than six months. “True Blue,” one of Madonna’s greatest albums, was, in fact, dedicated to Penn. In January 1989, just before celebrating their fourth anniversary, they decided to call it quits and got divorced.
Sean Penn and Madonna were, without a doubt, the pretty face of the early 1990s. She was just about to be crowned the Queen of Pop, and he already made some unerasable steps towards mega star success.
She was young, she was beautiful, and she carried her cutlery everywhere she went. Some of those might still be true, but it's still fun to see Reese Witherspoon enjoying herself so much. After a lifetime of playing bubbly blondes, Witherspoon has done plenty of roles that have earned her plenty of awards, like an Academy Award, an Emmy, and two Golden Globes.
This picture might have been from before all that, but it doesn't look like she has a care in the world as she laughs against a backdrop of leaves. This pic is from 1996, at the premiere afterparty of “Freeway.”
Who is this fabulously-dressed man, and when in the seventies was his picture taken? Well, he's Ian Ziering, best known as Steve Sanders on “Beverly Hills, 90210.” Of course, you probably know him as the voice of Vinnie on “Biker Mice from Mars.” And believe it or not, this picture was taken in 1992, just a few years after “Beverly Hills, 90210” hit television screens.
He's getting his groove on at the MTV Rock N' Jock Basketball Jam Benefit, but it doesn't look like anyone else is interested in dancing with him. We'll dance with you, Ian, even though to us, you will always be Steve.
Robert Downey Jr.
It comes as a surprise to some people that Robert Downey Jr. was such a big name in the nineties. He was in plenty of movies and played well-regarded roles, but his off-screen antics made it hard for him to break into the A-list. Stints in and out of rehab cooled his star before the Marvel Cinematic Universe came calling.
This picture has a young RDJ leaving or entering Madonna's New Year's Eve Party on December 31st, 1991. It kinda looks like he's dressed as Charlie Chaplin — a flashy suit, a white scarf, and a bowler hat give him a unique look that really seems to work.
Bruce Willis and Sylvester Stallone
You might remember going to an amusement park for your birthday or some other kind of special event as a kid. This picture just proves that celebrities are big kids at heart. This picture of a few big Hollywood names was taken at Demi Moore's thirtieth birthday party at Six Flags Magic Mountain in Valencia.
Closest to us is actor Bruce Willis, and next to him is fellow action star Sylvester Stallone. On Stallone's other side is his then-partner, Danish actress and supermodel Brigitte Nelson. There's some guy to her left who looks a little shell-shocked if you ask us.