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Actors Who Nailed Their Portrayals of Iconic Vintage Hollywood Stars

Madeline Hiltz
(Photo Credit: MovieStills DB and Bettmann/ Getty Images)

The Golden Age of Hollywood was truly an era like no other. Though it has long since passed, we still can’t get enough of vintage Hollywood. As such, many modern actors and actresses have starred as some of our favorite old-school celebrities. Here we take a look at contemporary stars who transformed into Hollywood legends.

Don Cheadle as Sammy Davis Jr.

Don Cheadle in The Rat Pack and Sammy Davis Jr

(Left) Don Cheadle as Sammy Davis Jr. in ‘The Rat Pack’ (1998). (Right) Sammy Davis Jr. in 1988. (Photo Credit: HBO/ MovieStills DB and Harry Langdon/ Getty Images)

In 1998, actor Don Cheadle starred as Sammy Davis Jr. in the made-for-television film, The Rat Pack. Cheadle won a Golden Globe for his performance.

Cheadle only had a few weeks to prepare for this role. In only a couple of weeks, he learned to sing, tap dance, play the drums and trumpet, and twirl six-shooter pistols like Sammy Davis Jr. did.

2. Katie McGuinness as Vivien Leigh

Katie McGuinness as Vivien Leigh and Vivien Leigh at the Oscars

(Left) Actress Katie McGuinness portrays Vivien Leigh in Netflix’s ‘Hollywood’ (2020). (Right) Vivien Leigh accepts her ‘Best Actress’ Academy Award, 1940. (Photo Credit: MovieStills DB and Bettmann/ Getty Images)

In 2020, Netflix released a miniseries called Hollywood that focused on a group of aspiring actors during Tinseltown’s Golden Age. Hollywood brought many famous figures back to life, including Anna May Wong, Hattie McDaniel, Rock Hudson, and Vivien Leigh.

Actress Katie McGuinness played Vivien Leigh. Leigh struggled with bipolar disorder, which was depicted in the miniseries.

3. Michelle Williams as Marilyn Monroe

Michelle Williams as Marilyn Monroe and Marilyn Monroe

(Left) Michelle Williams as Marilyn Monroe in ‘My Week With Marilyn’ (2011). (Right) Marilyn Monroe circa 1954. (Photo Credit: The Weinstein Company/ MovieStills DB and Baron/ Stringer/ Getty Images)

Michelle Williams truly captured the spirit of the late blonde bombshell in the 2011 movie, My Week With Marilyn. The film focuses on Marilyn Monroe during her time in England when she was filming the 1957 film, The Prince and the Showgirl.

Interestingly, Williams won a Golden Globe for Best Actress (Comedy or Musical) for her role in My Week With Marilyn. Monroe won the same award in 1960 for her role in Some Like It Hot (1959)!

4. Nicole Kidman as Lucille Ball

Nicole Kidman as Lucille Ball and Lucille Ball

(Left) Nicole Kidman as Lucille Ball in ‘Being the Ricardos’ (2021). (Right) Actress Lucille Ball circa 1955. (Photo Credit: MovieStills DB and Silver Screen Collection/ Getty Images)

Nicole Kidman stars as Lucille Ball in the recent blockbuster movie, Being The Ricardos (2021). As you can see, Nicole Kidman truly resembles the late Lucille Ball in the film. Ball’s daughter, Lucie Arnaz, later released a video on her Youtube Channel in October 2021 where she said that Nicole Kidman “became my mother’s soul.” She also said that the movie was “freaking amazing.” Sounds like we need to add this to our “must watch” list!

5. Cheryl Ladd as Grace Kelly

Cheryl Ladd and Ian McShane in Grace Kelly and Grace Kelly and Prince Rainer III

(Left) Actress Cheryl Lane and Ian McShane star in the 1983 movie ‘Grace Kelly.’ (Right) Grace Kelly and Prince Rainier III on their wedding day in 1956. (Photo Credit: MovieStills DB and Gilbert TOURTE/ Getty Images)

We can’t get over how similar these two shots are! The 1983 movie Grace Kelly did everything right when recreating Kelly’s wedding to Prince Rainier III. The dress actress Cheryl Lane wore as Kelly is nearly identical to Princess Grace’s real wedding dress.

6. Carroll Baker as Jean Harlow

Carroll Baker as Jean Harlow and Jean Harlow

(Left) Carroll Baker as Jean Harlow in the 1965 movie ‘Harlow.’ (Right) Jean Harlow circa early 1930s. (Photo Credit: MovieStills DB and Bettmann/ Getty Images)

In 1965, Carroll Baker starred as the original blonde bombshell, Jean Harlow, in the movie Harlow. This movie was released after Baker played a fictional Rina Marlowe in the 1964 movie, The Carpetbaggers. It is widely believed that the character Rina Marlowe is based on the real life of Jean Harlow.

7. Andra Day as Billie Holiday

Andra Day as Billie Holiday and Billie Holiday

(Left) Andra Day portrays Billie Holiday in The United States vs Billie Holiday (2021). (Right) Billie Holiday singing. (Photo Credit: MovieStills DB and UniversalImagesGroup/ Getty Images)

Actress Andra Day hit her portrayal of Billie Holiday out of the park. Day stars as the jazz singer in Hulu’s 2021 biopic, The United States vs. Billie Holiday. Day was initially reluctant to play Holiday. However, after accepting the role she went on to win a Golden Globe Award for Best Actress in a Motion Picture (Drama), and was nominated for Best Actress at the Academy Awards.

8. Austin Butler as Elvis Presley

Austin Butler as Elvis Presley and Elvis Presley

(Left) Actor Austin Butler portrays Elvis Presley in the upcoming biopic, ‘Elvis’ (2022). (Right) Elvis Presley performing Hillbilly Heartbreak on stage, circa 1956. (Photo Credit: MovieStills DB and Bettmann/ Getty Images)

Austin Butler stars as Elvis Presley in Elvis – one of the most highly-anticipated movies of 2022. The movie is set to drop in June of this year and will cover a 20-year span of Elvis’s life, including his rise to fame and unprecedented stardom. We’ll admit that we’re all shook up at the uncanny resemblance between Butler and Presley, making us even more excited for the movie to drop!

9. Renée Zellweger as Judy Garland

Renee Zellweger as Judy Garland and Judy Garland

(Left) Renée Zellweger as Judy Garland in the 2019 movie, ‘Judy.’ (Right) Judy Garland performs circa 1960. (Photo Credit: MovieStills DB and Keystone/ Stringer/ Getty Images)

Renée Zellweger earned herself a Best Actress Academy Award for her portrayal of Judy Garland in the 2019 biopic, Judy. Though many people praised Zellweger’s portrayal of Garland, she didn’t get the support of one critical individual – Judy Garland’s daughter, Liza Minelli.

Before the movie was released, Liza Minnelli shared on Facebook that she had “never met nor spoken to Renée Zellweger,” and expressed that she had no desire to see the movie.

10. Lou Diamond Phillips as Ritchie Valens

Lou Diamond Phillips as Ritchie Valens and Ritchie Valens

(Left) Actor Lou Diamond Phillips plays Ritchie Valens in the 1987 movie ‘La Bamba.’ (Right) Ritchie Valens poses for an album cover in July, 1958. (Photo Credit: Columbia Pictures/ MovieStills DB and Michael Ochs Archives/ Stringer/ Getty Images)

February 3, 1959, is widely regarded as “the day that music died” when singers Buddy Holly, Ritchie Valens, and “The Big Bopper” J.P. Richardson were killed in a plane crash. The 1987 film, La Bamba, follows the life and career of Ritchie Valens.

La Bamba also features the plane crash that killed Valens and the other musical icons. On the day the plane scene was set to be shot, Valens’s real family was advised not to come to set that day as the scene might be very emotional and traumatic for them to watch.

11. Jennifer Love Hewitt as Audrey Hepburn

Jennifer Love Hewitt as Audrey Hepburn and Audrey Hepburn

(Left) Jennifer Love Hewitt stars as Audrey Hepburn in the film, ‘The Audrey Hepburn Story’ (2000). (Right) Audrey Hepburn wearing one of Tiffany’s most expensive diamond necklaces before filming ‘Breakfast at Tiffany’s.’ (Photo Credit: MovieStillsDB and Bettmann/ Getty Images)

More from us: A Rare Peek at Classic Hollywood Stars at Home

Jennifer Love Hewitt looks eerily similar to actress Audrey Hepburn. Hewitt played the late starlet in the 2000 made-for-television film The Audrey Hepburn Story. The film gives the audience a look at Hepburn’s childhood during the Second World War, as well as her time as a successful Hollywood actress.

Madeline Hiltz

Maddy Hiltz is someone who loves all things history. She received her Bachelors of Arts in history and her Master’s of Arts degree in history both from the University of Western Ontario in Canada. Her thesis examined menstrual education in Victorian England. She is passionate about Princess Diana, the Titanic, the Romanovs, and Egypt amongst other things.

In her spare time, Maddy loves playing volleyball, running, walking, and biking, although when she wants to be lazy she loves to read a good thriller. She loves spending quality time with her friends, family, and puppy Luna!