Summary

• The challenge of portraying Frank Sinatra adds a new layer to Scorsese and DiCaprio's iconic collaboration streak.
• DiCaprio's lack of experience as a professional singer raises doubts about his ability to capture Sinatra's voice on camera.
• Scorsese's upcoming film might focus more on Sinatra's personal life, sparing DiCaprio from the challenge of emulating the singer's voice.

Leonardo DiCaprio's newly announced Frank Sinatra biopic with Martin Scorsese already has one glaring challenge. Following the critical acclaim of 2023's Killers of the Flower Moon, which earned 10 nominations at the 2024 Academy Awards, Scorsese has shown no signs of slowing down his remarkable filmmaking career. Scorsese's upcoming Jesus film has already been confirmed with Silence actor Andrew Garfield to star. DiCaprio is expected to take the lead in a long-awaited Sinatra biopic directed by Scorsese. The 81-year-old director has been trying to make a Sinatra biopic for nearly two decades and the project has been considered one of Scorsese's unrealized projects until now.

The currently untitled Frank Sinatra biopic will mark the seventh feature film collaboration between Scorsese and DiCaprio, adding to Gangs of New York (2002), The Aviator (2004), The Departed (2006), Shutter Island (2010), The Wolf of Wall Street (2013), and Killers of the Flower Moon. This iconic collaboration streak with Scorsese is second only to Robert De Niro, although DiCaprio remains tied with Harvey Keitel and Harry Northup at six appearances each until the Sinatra biopic is released. While another Scorsese and DiCaprio collaboration is undoubtedly something to get excited about, there is one major aspect of the project that could present a challenge.

Leonardo DiCaprio Has Never Portrayed A Famous Singer Or Sang In A Movie Before

DiCaprio had a very brief singing scene in Quentin Tarantino's latest film

While DiCaprio has certainly nailed the classic American look in films like The Great Gatsby and The Wolf of Wall Street, he has never been tasked with using his singing voice on camera before, other than a brief scene in Quentin Tarantino's Once Upon A Time In Hollywood.

The most apparent issue with DiCaprio portraying Frank Sinatra is the fact that he has no prior experience playing a professional singer in an acting role, especially not someone as iconic as Frank Sinatra. While DiCaprio has certainly nailed the classic American look in films like The Great Gatsby and The Wolf of Wall Street, he has never been tasked with using his singing voice on camera before, other than a brief scene in Quentin Tarantino's Once Upon A Time In Hollywood. As Rick Dalton is Tarantino's latest film, DiCaprio's small singing role was certainly nothing special and already casts some initial doubts about his ability to capture the iconic sound of Sinatra in Scorsese's biopic.

There is an off chance that Scorsese's film will focus more on his personal life of Sinatra than his performances and won't actually require DiCaprio to take on the challenge of emulating the legendary singer's voice. Unlike Austin Butler in Elvis and Timothée Chalamet in James Mangold's upcoming A Complete Unknown, DiCaprio might be spared from trying to sing like Sinatra, although that would essentially defeat the purpose of a biopic about the musical icon. Scorsese and DiCaprio have made movie magic for more than 20 years, which is more than enough to ensure confidence in their seventh collaboration. However, DiCaprio could be challenged like never before.

DiCaprio Admitted He Has A ‘Pretty Atrocious’ Voice After Failed Moulin Rogue Audition

DiCaprio was candid about his poor singing ability ten years ago

In an interview with Variety back in 2014, DiCaprio recalled his auditioning process for Baz Luhrmann's Moulin Rouge!, calling his singing voice "pretty atrocious."

DiCaprio was first rumored to be attached to Scorsese's Sinatra biopic in the late 2000s after John Travolta had initially been considered. DiCaprio was reportedly taking singing lessons in order to nail the part of Sinatra more than a decade ago, but the movie remained in development for years as both he and Scorsese had taken on other projects, which turned out pretty well for both of them. In an interview with Variety back in 2014, DiCaprio recalled his auditioning process for Baz Luhrmann's Moulin Rouge!, calling his singing voice "pretty atrocious." He added, "To be honest, I’m not really prepared to do a musical."

Playing Frank Sinatra Will Be One Of DiCaprio’s Most Challenging Roles Of His Career

Even DiCaprio will face scrutiny if his singing is not up to par

Both DiCaprio and Scorsese rarely ever miss, especially in their collaborative efforts, but this Sinatra biopic already sounds like their riskiest venture yet.

Both DiCaprio and Scorsese rarely ever miss, especially in their collaborative efforts, but this Sinatra biopic already sounds like their riskiest venture yet. DiCaprio has proven his determination as an actor over the years, from acting through a bloodied hand in Django Unchained to eating raw bison liver to earn his first Oscar in The Revenant. Of Scorsese and DiCaprio's six feature film collaborations, the least critically acclaimed is Shutter Island, which received a Rotten Tomatoes score of 69% and is still considered a celebrated film.

Scorsese and DiCaprio have given audiences very little reason to doubt them thus far. Still, DiCaprio will certainly be inviting increased skepticism by playing such a celebrated figure as Sinatra, even if he is one of the most bankable actors in Hollywood. DiCaprio's acting talents are in no way part of the concern for Scorsese's Sinatra biopic, which is also evidently a passion project more than two decades in the making. DiCaprio's fate as Sinatra will inevitably come down to the simple question of whether he can convincingly sing like the legend himself, or how Scorsese can creatively work around it if not.