Oscar's Red Carpet Hits & Misses

Cameron Diaz is a fashion risk-taker – and she did not disappoint red-carpet watchers at 2000’s Oscars. The former model showed off her runway-ready figure in this barely-there lace Versace frock. If you’ve got it, when is a better time to flaunt it than on Oscar night?

Fresh from her Golden Globes win for her turn as transgendered teen Brandon Teena in 2000, a radiant Hilary Swank showed her “metal” in this bronze Randolph Duke gown. She capped off the sparkling look with more than $250,000 worth of Asprey amp Garrard diamonds.

Statuesque Sigourney Weaver gave the red carpet a run for its money at the 2001 Oscars in a garnet Galliano for Dior gown, setting her miles apart in a sea of basic black. Bravo!

It can be a challenge to find a dazzling gown that doesn’t overpower a small frame, but petite Holly Hunter did just that in 1997. She ignited the Oscars that year in a simple Vera Wang sheath that showed off her shapely shoulders and helped usher in the “gauzy” look that would soon grace runways the world over.

Though a stylist helped Pollock’s Marcia Gay Harden achieve her stunning red-carpet look in 2001, her dad had the final word. “My father said to me, ‘Honey, I want you to wear a strapless dress,'” she told PEOPLE. “‘You’ve got what it takes to hold (it) up!'” Harden dazzled in this crimson Randolph Duke ball gown.

Minnie Driver showed off her 5’10” frame in 1998 in this elegant yet seductive ruby-red Halston dress with matching faux-fur stole. After perusing gowns by Gucci, Prada and Versace, Driver chose this unadorned number because “you have to sparkle, not your dress,” she told PEOPLE.

She will grace the annals of history as the first African-American to win a Best Actress Oscar (in 2002, for Monster’s Ball) – and the dress Halle Berry chose for the occasion was appropriately memorable. She was resplendent in this embroidered, burgundy Elie Saab gown, and accessorized with a $3 million orange “pumpkin” diamond ring, courtesy of Harry Winston.

In 2000, Girl, Interrupted star Winona Ryder showed off her love of elegant couture (no jokes, please) in a 1940s-inspired, figure-flattering, black strapless gown with a matching cream-accented wrap. Pulled-back hair, subtle-yet-sparkling jewelry and smoky eyes completed the classic, glamorous look.

It appears Angelina Jolie forgot which event she was attending when she donned this get-up to the 2000 Oscars. This look — stringy black locks, too-pale skin and boring black gown — is more appropriate for a Munsters reunion than the Academy Awards. Scary!

If you thought Cher had cornered the market for oddest Oscar looks, you must have missed the show in 2001, when Icelandic songstress Bjork wore this nude body stocking and swan tutu. She gets points, however, for finding shoes that matched.

Apparently Six Feet Under’s Rachel Griffiths missed the memo that said a dress is not supposed to attract more attention than its wearer. The small-screen siren wore this psychedelic pink number in 1999 and had onlookers running for their shades.

It’s not easy to look bad when you have a beautiful, statuesque figure – but Daryl Hannah seems to do it time and again. She’s a semi-permanent fixture on worst-dressed lists, and 1999’s Oscars were no exception: this dank, busy crushed-velvet number just does nothing for her.

In 2001, Best Supporting Actress nominee Kate Hudson (for Almost Famous) was at the top of her game. So why did she show up to the big event in this Chloe catastrophe that hides her curves? Kate: Take a cue from mom Goldie Hawn and find something cute that shows a little skin.

The brocade jacket that Best Actress nominee Meryl Streep sported for the 2000 Oscars was right on, but what’s up with those pants? She needed something much simpler to accompany that top.

Juliette Binoche likes to use the red carpet to play dress up; in the past she’s shown up dressed as a flapper and a ’40s pin-up doll. That’s all well and good, but she took things too far at the 1997 Oscars (when she won for Best Supporting Actress for The English Patient, playing the Countess of Monte Cristo in this over-the-top rust-colored cape-and-gown combo.

Somewhere over the rainbow … there was a color-blind stylist dressing Faith Hill for the 2002 Oscars. This frothy, peacock-inspired number is for the birds.