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20 Side-by-Side Pictures Of Actors Portraying Iconic Old Hollywood Stars

Stepping into the shoes of a character can be a tremendously complex process. Sometimes it requires lots of time to study and prepare for the role. But when playing a real-life character who is known to almost everyone, things can get even more challenging. In order to provide flawless depictions of these famous figures, actors put in a lot of work. From getting the particular character's lifestyle, costumes, and body language, everything is studied carefully because even the smallest detail may cost big at the box office.
But how many actors can portray well iconic old Hollywood stars in movies? From Michelle Williams as Marilyn Monroe in "My Week With Marilyn" (2011) to Nicole Kidman as Lucille Ball in "Being the Ricardos" (2021), we’ve compiled a list of the most accurate real-life portrayals ever shown on screen. Let's compare some of them with their real-life counterparts and see if these actors played them perfectly or not.

#1 Jennifer Love Hewitt as Audrey Hepburn

Iconic Old Hollywood StarsSource: GettyImages

"The Audrey Hepburn Story" is a 2000 American biographical drama television film based on the life of one of Hollywood's most famous actresses: Audrey Hepburn. Actress Jennifer Love Hewitt portrayed well the grace, poise, as well as fashion of our beloved actress.

#2 Sam Heughan as Paul Newman

Iconic Old Hollywood StarsSource: Sky Cinema/Getty Images

Sam Heughan portrays '60s icon Paul Newman in the 2021 film "To Olivia". In particular, he perfectly revived Paul Newman's voice, gestures, and other characteristics on screen.

#3 Beyoncé as Etta James

Iconic Old Hollywood StarsSource: Sony Pictures Releasing/TriStar Pictures/Getty Images

In the 2008 movie "Cadillac Records", Beyoncé took the role of Etta James and performs several songs from the singer’s catalog.

#4 Don Cheadle as Sammy Davis Jr.

Iconic Old Hollywood StarsSource: HBO/Getty Images

To play legendary singer Sammy Davis Jr. in "The Rat Pack", Don Cheadle learned to sing, tap dance, play drums, play trumpet, and twirl six-shooter pistols.

#5 Katie McGuinness as Vivien Leigh

Iconic Old Hollywood StarsSource: Netflix/Getty Images

In the TV mini-series "Hollywood" (2020), Katie McGuinness played the beautiful British actress, Vivien Leigh who is known for her glamorous curls and red lipstick.

#6 Keeley Hawes as Patricia Neal

Iconic Old Hollywood StarsSource: Sky Cinema/Getty Images

Patricia Neal is known as a stage and movie star who seems to have it all. But the movie "Dear Olivia" (2021) revealed her dramatic marriage to author Roald Dahl. From her jewelry to her brown hair, Keeley Hawes resembles Patricia Neal.

#7 Michelle Williams as Marilyn Monroe

Iconic Old Hollywood StarsSource: The Weinstein Company/Getty Images

In the 2011 film "My Week With Marilyn", Michelle Williams perfectly captured the spirit of the legendary blonde bombshell Marilyn Monroe. It's hardly surprising she won a Golden Globe for her performance thanks to her choreographed numbers onstage and her realistic costumes.

#8 Joaquin Phoenix as Johnny Cash

Iconic Old Hollywood StarsSource: 20th Century Fox + Getty

Joaquin Phoenix has an extensive filmography, but one of his most memorable performances is as Johnny Cash in "Walk the Line" (2005). He performed all the songs himself, learned to play guitar for the role, and won a Golden Globe for Best Actor.

#9 Renée Zellweger as Judy Garland

Iconic Old Hollywood StarsSource: Roadside Attractions/LD Entertainment/Getty Images

To perform the famous singer Judy Garland in the last years of her life in "Judy" (2019), Renée Zellweger learned to sing live and dance like the late singer. And as the result, she earned her first Best Actress Oscar.

#10 Jamie Foxx as Ray Charles

Iconic Old Hollywood StarsSource: Universal Pictures/Getty Images

Thanks to his role as Ray Charles in 2004's "Ray", Jamie Foxx earned his Best Actor Academy Award. "Give it up for Ray Charles and his beautiful legacy," he emotionally said during his acceptance speech, "Thank you Ray Charles for living."

#11 Nicole Kidman as Lucille Ball

Iconic Old Hollywood StarsSource: GettyImages

Nicole Kidman effortlessly reenacted both the most comical and dramatic parts of Lucille Ball's life in "Being the Ricardos" (2021).

#12 Kevin Kline as Errol Flynn

Source: Samuel Goldwyn Films/Getty Images

Thanks to his preparation, Kevin Kline completely transformed into the role of Errol Flynn in "The Last of Robin Hood" (2013).

#13 Justine Waddell as Natalie Wood

Source: GettyImages

From shoulder-length hair to dark brown eyes, the late Justine Waddell and Natalie Wood can be related, that is why Waddell was chosen in "The Mystery of Natalie Wood". The movie dived into Wood's entire career, from her early years to her tragic death.

#14 Rico Simonini as Frank Sinatra

Source: Gravitas Ventures/Getty Images

Rico Simonini perfectly embodied Frank Sinatra in the 2018 film "Frank and Ava", from his piercing eyes to his smooth-as-butter voice.

#15 Andra Day as Billie Holiday

Source: Hulu/Getty Images

The intense experience of portraying the legendary jazz singer Billie Holiday in "The United States vs. Billie Holiday" led Andra Day to consider giving acting a break. She said in an interview, "I've always loved actors and always had respect for them, but now I have a whole new respect for them and how deep they have to go". This role earned her a Golden Globe, a Grammy nomination, and three Oscar nominations.

#16 Chadwick Boseman as James Brown

Source: Universal Pictures/Getty Images

James Brown would have been pleased with how late Chadwick Boseman portrayed him in the 2014 film "Get on Up". This performance earned Chadwick Boseman an NAACP Image Award nomination for Outstanding Actor in Motion Picture. He trained for two months to learn how to sing and dance like the 1960s legend.

#17 Michelle Krusiec as Anna May Wong

Source: Netflix/Getty Images

In 2020, Netflix's "Hollywood" brought many legendary figures back to life. And Anna May Wong, who's considered to be the first Chinese-American movie star, is portrayed by Michelle Krusiec.

#18 Queen Latifah as Hattie McDaniel

Source: Netflix/Getty Images

Also in "Hollywood", Queen Latifah brought her talent to the small screen as Hattie McDaniel, the first Black Oscar winner.

#19 Jake Pickings as Rock Hudson

Source: Netflix/Getty Images

The last actor on this list from Hollywood is Jake Pickings, who took on the role of Rock Hudson. He's the spitting image of the '50s leading man, from his hairstyle to his height.

#20 Javier Bardem as Desi Arnaz

Source: Amazon Studios/Getty Images

By embracing the character of Desi Arnaz in "Being the Ricardos", Javier Bardem overcame his fear of singing. He also took guitar, conga, and dialect lessons for the role.
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