Oscar night is the biggest evening of the year for Hollywood. Though actors aren’t the only ones strutting down the red carpet in glittering, and sometimes shocking, couture. Check out our roundup of the most outrageous outfits worn by musicians at The Academy Awards. From Cher’s extravagance to Madonna and Michael Jackson pairing, check out who made the cut.
One of the most iconic images from the Oscars is Barbra Streisand working a sheer Arnold Scaasi look complete with a white color, matching cuffs and a giant bow. We love this pilgrim gone bad look.
Bette Midler hit the scene at the 54th Annual Academy Awards looking like a golden disco ball on March 29, 1982.
Madonna and Michael Jackson
The King and Queen of Pop united at the 63rd Annual Academy Awards in 1991. Madonna Channeled Marilyn Monroe as she arrived to the after party at Spago's in a glittering Bob Mackie gown with Michael Jackson, who looked equally glamorous.
Icelandic singer Bjork, rocked one of the most iconic Oscar dresses of all time. This white swan dress designed by Marjan Pejoski has gone down in history, for better or for worse.
Diana Ross looked angelic in a glittering white gown as she performed with the debonair Lionel Richie at the 54th Annual Academy Awards on March 29, 1982.
Juliette Lewis caught the attention of many when she hit the red carpet sporting cornrows at the 64th Annual Academy Awards Academy Awards back on March 30, 1992 with then-boyfriend Brad Pitt at her side.
Beyonce jazzed up the 81st Annual Academy Awards on Feb. 22, 2009 with a killer performance with Oscar host Hugh Jackman. The singer stunned in a glittering red bustier and top hat.
Celine Dion caused many to do a double take as she hit the red carpet at the 71st Annual Academy Awards held on March 21, 1999. She showed up in a baggy white suit with a backwards jacket, matching fedora and sunglasses. This look is just as odd from the front as it is from the back.
Chris “Ludacris” Bridges looked dapper in a velvet blazer at the Vanity Fair Oscar Party back on March 5, 2006.
Cher made her Oscar debut back on March 27, 1973 at the 45th Annual Academy Awards with Sonny Bono. For her first Oscar run, Cher wore Oscar gold with a glittering look while showing off her toned tummy. She stole the show at the 1986 Academy Awards in 1986 by working a fabulous showgirl-worthy Bob Mackie beaded black costume with an Amazon worrier-like 2-foot headdress. And in 1998, Cher showed off her love for theatrics while wearing a nude art deco-inspired number.
Dolly Parton presented an award and performed at the 78th Annual Academy Awards show on March 5, 2006. The country singer looked pretty in pink wearing a delicate pastel dress by Robert Behar.
Faith Hill performed “Somewhere Over the Rainbow" at the 2002 Oscars in a sorbet-hued Versace gown, perfectly echoing the song.
Jennifer Hudson worked a chocolate gown styled with a metallic cropped jacket by Oscar de la Renta as she was named Best Supporting Actress for her role in “Dreamgirls” at the 79th Annual Academy Awards held on Feb. 25, 2007.
Jennifer Lopez showed off her famous curves as a presenter at the 82nd Annual Academy Awards on March 7, 2010 in an Armani Privé Spring 2010 pale pink gown.
Three 6 Mafia
Three 6 Mafia brought bad boy swagger to the 78th Annual Academy Awards on March 5, 2006.