This is a fun question to ponder. Leonardo DiCaprio has been acting on screen since 1991 – about 33 years. His current age is around 50. Frank Sinatra started singing professionally in 1935. He turned 50 in 1965.

We’ll start there as our baseline, making things fairly equal in the world of 50-year old male human instruments.

Jumping back to “The Tonight Show” in 1965. Dean Martin and Frank Sinatra show up to harass fellow ratpacker and substitute host Joey Bishop. They’re clearly more than a few cocktails in and smoke like chimneys for the interview portion until Mr. Sinatra gets up and sings “Angel Eyes” with the band. The age on his voice is there, you can hear the some creaks and gravel, but he still belts it out live (extremely well) and his vocal performance (interpretation of the song) is really spot on.

What really stands out in the performance is how free and yet still in control Sinatra is. He does use his full voice, not parts of his voice (resonance would be missing) and even when he is singing the softer passages, there is still power behind it (think “loud talker” crooning). After all, he’s been at it for three decades here and he knows what he’s doing. He’s not “trying” or “working.” He’s a little tipsy and not sweating it. He’s not even concerned about entertaining us. He tells us at the outset that he is taking on the role of a saloon singer – a role he knows well. Once he announces this, Dean Martin jumps in with a joke, Sinatra laughs and moves seamlessly into the song – and the saloon. The audience goes right with him and Sinatra holds their focus in the palm of his hand. It’s a short song, a pretty melody, and a powerful performance.

Here’s approaching 50 Leo singing in character as Rick Dalton from “Once Upon A Time In Hollywood,” a role ostensibly based on a variety of non-singing actors from the 1960’s like Burt Reynolds, William Shatner, Edd Byrnes, George Maharis and others.

And, of course, it’s as awful as it’s supposed to be. What’s surprising about this performance though, in its funny/hack-kind of “Anti-Sinatra” way, is that Leo DiCaprio – one of the most watchable, energized, interesting and captivating screen actors over the last three decades – manages to turn himself into a vocal performer with all the power and relevance of a flea on an elephant. That is an accomplishment. It’s hard to be that bad.

So, how could a 50 year-old DiCaprio develop his voice into the iconic 50 year-old Sinatra sound?

“Work Heavy” – The resonance of Sinatra’s voice was magical – particularly for a guy who was 5’8″. It was not a light sound, it was a heavy sound. Sinatra could croon, yes, but he was a belter. He came up through the “minor leagues” in the early 1930’s when microphones were new to live performers. He learned how to use his full voice and be heard. That use of vocal energy continued throughout his performing life. Leo, put your back into it, belt it out and practice being the loudest guy in the room. Practice dominating the room with a big, heavy voice. You’ll get used to it.

“Intonation” – This is a high hurdle. There is no male pop singer in history who could utilize vowels, consonants and diphthongs like Sinatra. This skill had to have its origins in his Catholic upbringing. The mass was exclusively spoken and sung in Latin during his youth. Learn how to sing in Latin as a kid and you will know how to intonate. Phonics (how to “sound out” words) would have been how he learned to read in school, another huge assist. He wasn’t fluent in Italian, so we’ll take that off the table. Think of how the painters who studied the Dutch Masters became Impressionists. Sinatra’s early musical environment of sustained vowels sung in church, group singing and, later, Tommy Dorsey’s breath control, phrasing and tone on the trombone in clubs and concert halls led him down the path to his spectacular, rule-breaking intonation.

“Phrasing and Storytelling” – Even though Sinatra won an Oscar for Best Supporting Actor for “From Here To Eternity” in 1954, his acting didn’t exactly set the standard for actors in the future. Far from it, really, as actors are now better than they’ve ever been. BUT, Sinatra’s phrasing, storytelling and delivery have set a standard that is now rarely reached by other pop vocalists. It’s a big subject, as simple as it is complex, and I’ll break it down in a future item.

Circling back, “could” Leonardo DiCaprio sing like Frank Sinatra? Yes, of course. Heavy up your voice, get some strength and learn his intonation. The challenge, the defining challenge, will be to deliver a song like Sinatra. There’s a lot more than singing going on.