Could Leo DiCaprio Sing Like Frank Sinatra in a Biopic? Sure!

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.

Removing The Doubt In Vocal Performance

When it comes to vocal performance, I guess we can put “doubt” and “fear” into the same wordsphere. Only problem is that doubt and fear are extremely personal; based on a performer’s lifetime of unique experiences. When I was 17, I sang “Yankee Doodle Dandy” in front of a halftime homecoming crowd. I was decked out in a sequined white tux with tails (thanks, Michelle!) and a stars and stripes top hat. Cheerleaders were in position down on the field – maybe they formed a star, I don’t remember that part very well, but I do remember that I sang and danced on that field. And my microphone was off. The whole time.

The microphone didn’t have an on/off switch, so there wasn’t much I could do about it. As I was performing what appeared to be a mime act, Donna, one of the celestial cheerleaders said, “Your mic’s not on.” And I said, “Yeah, I know” and kept dancing (box step, walk, walk, grapevine…).

When I quietly left the field with the cheerleaders, Scott the sound guy confirmed on the sidelines that, yup, my mic was off the whole time. The drama teacher, Mr. Ruehle, saw my reaction to that news and complimented me on my professionalism, mentioning how I just “shook it off.”

It was disappointing for sure, but I did shake it off. You see, just two years prior, at the gargantuan annual high school musicale extraordinaire held in the sold-out gymnasium, my mic was off for the entirety of my big solo debut at my new school. Now, that was horrifying.

Performing can be a very humbling experience and your willingness to surrender to mayhem is one of the keys to happiness.

So, as a vocal performer, what is in your control?

The Lyric.

You can’t do much about the mic, the mixer, the accompanist or the sound system, but you can know your lyrics inside out.

Here’s your checklist:

  1. Without singing it, how fast can you enunciate every word of the song in a monotone with no spaces/word stretches? Can you do it in under 30 seconds? Time it.
  2. How few breaths can you take in that 30 seconds? One? Two?
  3. Can you look at or read an article on your phone while saying your lyrics as quickly and as understandably as possible? Can you then tell us what the article was about?
  4. While facing in one direction, focus on one item in the room and tell the lyrics to that item, then change to north, south, east or west, focus on another singular item, repeat and continue.
  5. Be joyful in your practice.

Performance 101: The Tri-Force Of Performing

Performing with a busy brain is exhausting. Performing with worry or anxiety is, really, not performing at all. What kind of performance can an artist give if they’re stressing out whether the microphone will cut out or a wardrobe malfunction is about to happen or a set piece is about to fall over?

Problem is, much of the aforementioned is out of your control anyway, so you have to trust the others who actually control those aspects to do their jobs. And they will because they are almost as exposed in their job as you are in yours.

What you CAN control is much more important and the reason for everybody gathering together in the first place.

You are in control of the energy.

What you deliver is energy. Focused energy.

A busy, unfocused mind in performance is a torturous thing to watch.

How do we unbusy the mind?

“Energy, Attention, Awareness”

That is our performance mantra and it is fundamental to our work.

If you’re nervous before a performance, join the club, but why focus on nerves when you have a job to do (that you love)?

Focus on Energy, Attention, Awareness.

Take time to figure out what each of these words means to you before and during your performance and utilize these fundamental ideas to unbusy your mind and clarify your focus.

Performance 101: Creative (Empty) Space In Your Brain

Great performers are like race car drivers; the idea being that, in order to win the race, one needs to stay in the moment, assume a calculated amount of risk and operate instinctively and creatively when the opportunity arises.

The simple goal of a pro race car driver is to win the race.

What are some of the “simple” goals of a singer in a performance?

Get all the words right?

Sing all the notes right?

Make a beautiful sound?

Truth is, those are the initial rehearsal goals achieved with hours of practice. “Getting the song into your body.” While these goals provide the basis of performance, if that is all you intend to give your audience, it’s definitely time to upgrade your approach.

Performance Goal: Creative Open Space In Your Brain

Basic: Be able to say the lyrics as fast as you can say the ABC’s – without thinking about the order of the letters and without singing the song. Say them in a monotone very quickly, do not accent or stretch out the words. Move your lips and mouth in an animated/exaggerated way. Be able to plunk out the melody – one note at a time – on a keyboard. Be able to use the same vocal tone (dark, warm, brassy, bright, light, etc.) throughout the entirety of the song. If you have to change your tonal quality to hit a high note or rumble a lower note, chances are you need to find a more suitable key for your song.

Advanced: Having set the muscle memory (remember, race car drivers drive in a circle for hours), now we let go of the worry and practice creative risk. Creative risk involves letting go of anxiousness, trusting that you have drilled the basics and are ready to live in the moment on stage. Thoughts and thought impulses beget words (for some, it’s the other way around, but we call those folks thoughtless anway). Your goal now is to live within the thoughts of the lyric and having/experiencing/expressing each thought before actually singing the lyric. Now your brain is full again, but it is focused and there is no room for anxiety. It takes energy, concentration and a whole lot of pretending to stay there, but by upgrading your performance approach, you can enjoy sharing a song as much as your audience can enjoy receiving it.

Singing 101: Jobs For Singers

For many years, I’ve had a running joke with my kids. At random inopportune moments I would ask them, “Hey, would you like a free song? I’m a professional singer. No charge.”

To which they’d respond, “No, Dad, I don’t want a song right now.”

“But it’s a really good song and I’m a great singer. And it’s free.”

“No. Go away.”

“It’s FREE – other people would have to pay to hear me sing. This won’t cost you a dime! This is a great offer!”

“No thanks.”

But, feeling generous, I’d usually launch into a song anyway. Typically, “Zip-A-Dee-Doo-Dah,” a terrifically catchy song in my opinion, and they’d keep playing their video game…Win/Win.

Here’s the thing: Singers Are Their Own CEOs.

As a singer, you are your own Chief Executive Officer from the very start. If you’re “hired” by a theme park, cruise line, restaurant, Broadway show or tour, record label, video game company, animation house, Film/TV production house, chances are that even if you deliver a great/fantastic/amazing job as a singer, you won’t end up being named the president of that theme park, cruise line, restaurant, record label, etc. Corporate upward mobility is not a thing for singers. We create our business. We drive our business. We are the CEOs of Singing, Inc.

Basic (Paying/Post-Covid) Jobs For Singers: Church gigs (include weddings and funerals), theme parks, cruises, live corporate industrials, restaurants/karaoke bars, rest homes, Christmas caroling groups

In-Between: Produce music, play music, write/compose music, read music, record music and appreciate ALL music. And while you’re adding these skills to your toolkit, practice singing, stay in shape and never turn down an opportunity to sing, even for no money. Get the work in until the day arrives when you don’t need the work.

Advanced (Better Paying/Post-Covid) Jobs For Singers: Recording (anything and everything including Voiceover work), Anything contracted via SAG/AFTRA/Equity/Musician’s Union, Animation, Film/TV, Broadway and tours, video games.

Summary: Writers write. Dancers dance. Singers sing.

Singing 101: Smoke, Fires, Vocal Irritation and Preventative Measures

Ah, 2020…a pandemic, social injustice, a recession, climate change, a divisive fool in the White House, no live music or performance since mid-March and now the West Coast is on fire. I hesitate to ask what else could be thrown our way in case a meteor is currently considering the Los Angeles Basin a fun landing spot in the next few months. Don’t wanna jinx anything.

Heavenly bodies aside, let’s discuss toxic air and how to deal with it as a singer.

Basic: When faced with smoke and air pollution, your body will create all kinds of defenses, but our immune systems can only do so much, so stay out of it. If you don’t need to go outside, don’t go outside. Get an air purifier with a decent filter. Fires aren’t just burning trees in the forest, they’re burning cars, buildings – anything that will feed the flame. Dioxins – the byproduct of these fires – are incredibly dangerous to our lungs, hearts and overall health. However, indoor pollution from these fires is just as bad – if not worse – so make sure the air conditioner in your apartment or house has a clean filter and that the windows and doors in your place are properly sealed. Your pets will thank you, too.

Advanced: Once in your lungs, PM10 and PM2.5 (microscopic particulate matter sizes) remain resident. You can’t cough them out. N95 and N99 masks have proven helpful in the reduction of particulate matter taken into the body via mouth and nose, but remember that your skin – your largest organ – can also absorb pollutants, so, along with your mask, cover up with long sleeves, pants, etc. There’s no such thing as healthy smoke. Be aware that hanging around the barbecue on the weekends ain’t doing you any favors, either.

Summary: As singers, our performance spaces can be hot, cold, dusty, moldy, dry, damp, odd places. There’s no need to act like a germophobe, but we have plenty of reasons to reduce the risk of bacterial infections, lowered immunity by being proactive. After all, we are living instruments.