1 of 8
ANNE AS JUDY
With her big eyes, full lips and brunette waves, Anne Hathaway has drawn comparisons to Hollywood's Golden Era star Judy Garland. Even more uncanny, the 28-year-old can hold a tune with the best of them – check out her amazing rendition of Les Misérables' "On My Own" at this year's Oscars! No wonder Hathaway, who gamely spoofed The Wizard of Oz on Saturday Night Live in January, has been tapped to play Garland in an upcoming biopic of the star's troubled life.
2 of 8
JENNIFER AS BARBRA
Cover girl Jennifer Aniston channeled larger-than-life diva Barbra Streisand for a Harper's Bazaar photo shoot based on Streisand's iconic film moments – right down to the long nails and signature '60s coif! – in September 2010. Babs's take on the shots? "I think she did a wonderful job!" the fellow New Yorker gushed, before adding, "if only she had a bump on her nose!"
3 of 8
BEYONCé AS PAM
For her big-screen debut in Austin Powers in Goldmember, Beyoncé stole the show as Foxxy Cleopatra – a cheeky 'froback to '70s blaxploitation queen Pam Grier (Foxy Brown). "My mother is a Pam Grier fan," the 29-year-old told Jay Leno of her inspiration for the role. "And I went and watched all [her] movies. And now I'm a huge fan."
4 of 8
KATIE AS JACKIE
For a moment, it looked as though the public would never get to see Katie Holmes step into the formidable shoes of Jackie O. in The Kennedys, but the miniseries based on the famous First Family is finally showing just how much work the 32-year-old star put into the role. "[It] was overwhelming because she is such an icon, so I did a lot of research," Holmes tells EW. "It furthered my adoration."
5 of 8
PENéLOPE AS SOPHIA
Her most famous collaborator, Pedro Almodévar, told the New York Times in 2009 that Spanish muse Cruz belongs to the Mediterranean school of acting – carnal, gutsy, cleavage-heaving, loud – a style mastered by Italian screen goddess Sophia Loren. When Cruz got to work with Loren that same year on Nine, she gushed to Interview of her screen idol, "She looks like a goddess."
6 of 8
HALLE AS DOROTHY
Halle Berry's connection to the first African-American Best Actress Academy Award nominee runs much deeper than just skin deep: Berry played Dandridge in a TV biopic based on her life, for which she won an Emmy and a Golden Globe in 2000. Two years later, when Berry became the first African-American to win a Best Actress Oscar (for Monster's Ball), she paid a touching tribute to the '50s-era pioneer.
7 of 8
RACHEL AS HEDY
It makes perfect sense that the Cambridge-educated British actress, known for her brains and beauty, has been in talks since 2009 to star as '40s movie Hedy Lamarr (famed for starring in Cecil B. DeMille's Samson and Delilah). The biopic will shine light on the Hungarian's second, notable career as an accomplished scientist whose invention guided World War II torpedoes by radio control.
8 of 8
GWEN AS JEAN
With her golden pin-curls and signature red lips, Gwen Stefani has long drawn inspiration from original platinum blonde star Jean Harlow. Their remarkable likeness didn't go unnoticed by Martin Scorsese, who cast the No Doubt singer as the '30s screen siren in the 2004 Howard Hughes biopic The Aviator. "[Scorsese] gave me my first role in a major film, Howard Hughes gave Jean Harlow her first big lead role," Stefani marveled to MTV about the parallels between her and Harlow.
Playboy Says Goodbye to Hugh Hefner By Making Him the First Man To Ever Grace the Magazine's Cover Solo
From Gord Downie to Hugh Hefner: Remembering The Stars We've Lost in 2017
How Stars Dressed Up for Halloween Before They Were Famous
The Pop Culture-Inspired Costumes You Should Definitely Skip This Halloween
Watch Julianne Moore, Emma Stone and Melissa McCarthy Urge You to Demand Stricter Gun Laws