With the April 17th news that Martin Scorsese wants to cast Leonardo DiCaprio as Frank Sinatra in a film also starring Jennifer Lawrence as Ava Gardner, we’re looking back at our list of actors who could’ve nailed a portrayal of Sinatra.
While musicians still act in films and series today, it’s nothing like the Golden Age of Hollywood, when stars were often expected to be both singers and actors. Most of the biggest stars of the time were successful musicians, from Bing Crosby and Elvis Presley to Dean Martin and Judy Garland. One of the most famous of these stars was none other than Frank Sinatra.
The crooner was known for his smooth and distinct singing voice, but Sinatra was also an established actor. Starring in movies such as Our Town, Suddenly, From Here to Eternity, and The Manchurian Candidate, Sinatra proved himself to be a talented asset to Hollywood. He was prolific in both music and film, and had a suave charm to him that makes it difficult to picture anyone playing him in a movie.
There is only one Frank Sinatra, but there are gifted actors working today who could take on the gargantuan task of portraying one of Hollywood’s most iconic stars. While Martin Scorsese wants to cast Leonardo DiCaprio as Frank Sinatra in a biopic, here are nine actors who would be great in the role if DiCaprio doesn’t work out (and an explainer of why DiCaprio deserves the role).
10 Hugh Jackman
He may be universally known for playing Wolverine, but Aussie actor Hugh Jackman is a song-and-dance man at heart. Before he ever stepped foot into the world of Marvel superheroes, he was in stage productions of musicals such as Rogers and Hammerstein’s Oklahoma! Jackman recently went back to his musical theater roots when he reprised his 2004 role as Harold Hill in the Broadway revival of The Music Man.
10 Quintessential Frank Sinatra Movies
Sinatra displayed the power of his acting chops in dozens of movies throughout his career.
Why He’d Be Perfect as Sinatra
There is no questioning Jackman’s ability to carry a tune or his ability to lead a movie in a starring role. He’s played desperate fathers, superheroes, and magicians. He can easily slip into any role. Jackman has proved he can both lead a movie and sing throughout it with movies such as The Greatest Showman. He has the perfect skill set to be able to portray one of Old Hollywood’s greatest stars with conviction. He doesn’t sound like Sinatra, but being a professional Broadway singer, he could train his voice to mimic the crooner’s distinct voice.
9 Ewan McGregor
Ewan McGregor has showcased his ability to handle essentially any character thrown his way over the last 30 years. From a struggling addict to a Jedi to a lovesick writer, McGregor’s acting capabilities are versatile. He can transform himself into his characters, adopting a variety of accents and appearances.
Why He’d Be Perfect as Sinatra
Aside from his impressive acting abilities, McGregor is musically talented as well. He has proven perfectly capable of performing a wide range of songs when he played Christian in Moulin Rouge! The film features songs by Elton John, Madonna, The Police, and many more that were musically arranged to fit the movie, so he is more than capable of handling demanding songs. He also has plenty of experience leading a movie, so there is no doubt he would be able to convincingly portray the beloved actor.
8 Harry Connick Jr.
Harry Connick Jr. might be the most obvious choice to play Sinatra in a film. Not only did he meet with and sing for Sinatra numerous times in the past (see the above video for more), but he also has quite a set of pipes himself. HCJ has been lending his vocals to movie soundtracks for years now and has acted in some of these movies as well.
Why He’d Be Perfect as Sinatra
Similarly to Sinatra, HCJ has a powerful singing voice that could easily mimic Sinatra’s. He has covered Sinatra songs before, perhaps mostly famously in When Harry Met Sally where he covered “It Had To Be You”. His extensive musical background combined with his acting experience would give him the tools he needs to play the Hollywood legend. Plus, he actually has a similar facial structure to Sinatra.
7 James Marsden
Hairspray
- Release Date
- July 19, 2007
- Runtime
- 115
The severely underrated James Marsden has been consistently landing roles in both movies and TV shows for years now and has been a part of major franchises such as X-Men. He has been the leading man in rom-coms and comedies and has been in film adaptations of popular books such as The Notebook. Marsden has also been on highly successful shows such as Westworld and Dead to Me. He is a talented actor who deserves more leading roles.
Why He’d Be Perfect as Sinatra
Marsden has a similar physical appearance to Sinatra which could help audiences suspend their disbelief to believe that they are actually watching Sinatra. He also has experience singing in movies, most notably in Hairspray, where he played TV host Corny Collins. There is obviously a lot of singing involved in the movie, and Marsden had an entire opening number to perform to introduce his character’s show. The movie takes place in 1963, so Marsden also has experience acting in a decade that Sinatra was actively working in.
6 Ryan Gosling
Since he was a kid on The Mickey Mouse Club, Ryan Gosling has been capturing audiences’ attention for nearly 30 years. He has cultivated a lengthy filmography for himself, starring in mega-hits such as Blade Runner 2049 and Barbie. Gosling has tested his acting chops in numerous genres including drama, sci-fi, and comedy. He’s been nominated for Academy Awards both times he has sung in films, with Best Actor at the Oscars for his performance in Damien Chazelle’s La La Land, and Best Supporting Actor for Barbie. The man knows what he’s doing when it comes to acting.
Why He’d Be Perfect as Sinatra
As most of us already know, Gosling can act, sing, and dance. La La Land solidified his ability to use all three skills at once. He is also an underrated comedic genius. He can effortlessly portray serious characters, as shown in Drive, but he excels in comedic roles. His work in movies such as The Nice Guys, Barbie, and Crazy, Stupid, Love is evidence that he can easily get an audience to laugh. Sinatra dabbled in comedy too, and Gosling could portray that side of him as well.
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5 Robert Downey Jr.
Chaplin
- Release Date
- December 17, 1992
- Runtime
- 143
One of the greatest actors of his generation, Robert Downey Jr. has proved time and time again that he can slip into any role and churn out a show-stopping performance. He may be known for playing Marvel superhero Iron Man a.k.a. Tony Stark better than anyone could have, but his ability to nail the inner workings of a character reach far beyond that. He can do comedy, drama, romance, and action to name just a few. Some of his best work is his least talked about, such as his performances in Natural Born Killers and Kiss Kiss Bang Bang.
Why He’d Be Perfect as Sinatra
RDJ has never given a poor performance, even if the movie itself wasn’t well received. He has also played a real-life actor before in Chaplin, where he played the legendary Charlie Chaplin and was nominated for Best Actor at the Oscars in 1993. If he can play one Hollywood icon, he can play another. Something people may not know about RDJ is that he can sing quite well. He sang the song in the end credits of Kiss Kiss Bang Bang, “Broken,” and released an album in 2004 called The Futurist.
4 Andrew Garfield
Andrew Garfield is inarguably one of the most gifted, accomplished actors working today. Similarly to RDJ, Garfield has never given a bad performance. He has a diverse filmography, starring in both indie films and major blockbusters, and completely devotes himself to whichever character he is playing. It is no secret that he was incredibly passionate about playing Spider-Man in The Amazing Spider-Man movies, but he has given passionate, dedicated performances in all his movies. He has worked with master directors like Martin Scorsese in Silence, and he has been the highlight of indie movies like Mainstream.
Why He’d Be Perfect as Sinatra
Since he has an unwavering dedication to every role he plays, there is no doubt he would go above and beyond to accurately learn the mannerisms and personality of Sinatra to play him to the best of his abilities. When Garfield learned that Lin Manuel Miranda wanted him to portray theatre composer Jonathan Larson in tick, tick… BOOM! he learned how to sing and play the piano. In addition to Jonathan Larson, he has played another real-life figure in The Eyes of Tammy Faye where he played televangelist Jim Bakker. He knows his way around a biographical film, and he can sing now too.
3 Tom Holland
Tom Holland made a name for himself in the industry when he made an appearance as the MCU’s version of Peter Parker in Captain America: Civil War in 2016 and his career has not lost momentum since. Before his MCU appearance, Holland was able to work with actors such as Naomi Watts, Cillian Murphy, Ewan McGregor, and Tom Hardy, and since then, he has worked with Mark Wahlberg and Robert Pattinson.
Why He’d Be Perfect as Sinatra
Granted, Holland would play a very young Sinatra, but he would ace the role. In addition to his acting career taking off, Holland has a musical theatre background that would prepare him to take on the role. He starred as the title character in Billy Elliot from 2008 to 2010 in London. About eight years later, Holland proved his stage skills once again when he appeared on Lip Sync Battle to perform renditions of “Singin’ in the Rain” and “Umbrella” by Rihanna. He has an effortless stage presence that would allow him to tap into the essence of Sinatra’s song-and-dance personality.
2 Joseph Gordon-Levitt
500 Days of Summer
- Release Date
- August 7, 2009
- Runtime
- 95 Minutes
Joseph Gordon-Levitt has been acting for 35 years, since was about seven years old. For the early part of his career, he mostly had quick parts in movies and TV shows, but by the mid-90s, he started to gain traction when he landed a permanent role in the show 3rd Rock from the Sun. Since then, he has starred in acclaimed movies such as Inception, The Dark Knight Rises, and Lincoln.
Why He’d Be Perfect as Sinatra
JGL has a certain charm about him that translates well on screen. That charm would help him tap into the charismatic persona that Sinatra was known for. He’s an established actor who also has experience playing a real-life person since he played Edward Snowden in the biographical thriller Snowden. While he doesn’t look exactly like Sinatra, he has a similar facial structure and hair color that would be convincing enough. He has also tested his singing abilities in movies like 500 Days of Summer and The Muppets.
1 Leonardo DiCaprio
Leonardo DiCaprio is now the most likely choice for an actor to play Sinatra, considering Martin Scorsese pursuing the biopic. The pair have developed a rich relationship over the past 25 years, with Scorsese often bringing out the best of the actor in films like Gangs of New York, The Wolf of Wall Street, Killers of the Flower Moon, and Shutter Island. If Scorsese gets the film greenlit, it’s almost a sure bet that DiCaprio will star.
And that’s a good thing, depending on what era of Sinatra’s career that the film will explore and whether the film will be a musical. DiCaprio would need to be dubbed, most likely, if he has to sing in character. The actor was actually in the running for Moulin Rouge but couldn’t sing well enough to get the role, and his singing in Once Upon a Time in Hollywood leaves much to be desired. But in films like The Great Gatsby and the aforementioned Tarantino movie, DiCaprio proved that he could master the suave masculinity of Sinatra. We shall see.
