Mike Elson

Mike Elson

FOUNDER | CEO

04/22/2026 |5 min to read

How to Sing Like Frank Sinatra

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Singer practicing Frank Sinatra vocal style

Develop Smooth Control, Phrasing, and Timeless Style 

 There is a reason Frank Sinatra is still known as “The Voice.” When you listen to him, it feels effortless. His singing sounds smooth, relaxed, and deeply expressive, almost like he is speaking directly to you. 

For many singers, this level of control can feel intimidating. It is easy to think that this kind of voice is something you are born with. The truth is that Sinatra’s sound came from technique, discipline, and deep understanding of his voice.

If you are just starting, this beginner singing guide will help you build a strong foundation.

Learning how to sing like Frank Sinatra is about mastering breath control, phrasing, and storytelling while keeping your delivery natural and connected.

Mastering Breath Control

Breath is the foundation of Sinatra’s sound.

He was known for singing long phrases without breaking the line. This creates a smooth and connected style called legato.

Controlled Breathing Technique

  • Inhale quietly through your nose or mouth
  • Let your abdomen expand naturally
  • Keep your shoulders relaxed
  • Release air slowly and steadily while singing

Strong breath control helps improve your pitch accuracy and vocal stability.

The “Pinhole” Breath

Sinatra used small, controlled breaths instead of large gasps.

This allowed him to continue phrases without breaking the flow.

Practice taking small, silent breaths to maintain smooth delivery.

Phrasing and Timing 

Once you have the breath to sustain the notes, the next step is mastering how you deliver them. This is called phrasing. If you were to sing a song exactly as it is written on the sheet music, hitting every beat precisely on the nose, it might sound technically correct—but it wouldn't sound like Sinatra.

Singing Behind the Beat

One of Sinatra’s most unique traits is his timing.

He often sang slightly behind the beat, creating a relaxed and conversational feel.

This technique requires strong awareness of rhythm and control.

Legato Singing

Sinatra connected words smoothly.

Instead of separating each word, he allowed phrases to flow naturally.

This improves vocal control and creates a more polished sound.

Storytelling Through Singing 

Sinatra treated every song like a story.

Natural Delivery

Speak the lyrics first as if you are telling someone a story.

Then sing them with the same intention.

Clear Diction

Every word should be understandable.

Clear diction improves communication and emotional impact.

Tone and Resonance

Sinatra’s tone was warm and rich.

This comes from relaxed vocal production and proper resonance.

Building vocal strength will help you maintain a consistent tone across your range.

Using the Microphone Effectively 

Sinatra used the microphone to enhance expression.

  • Sing closer for softer, intimate moments
  • Pull back slightly for stronger sections

This creates dynamic contrast and emotional depth.

Suggested Song for Practice 

To apply these techniques, practice with:

This song is ideal because:

  • It focuses on smooth phrasing
  • It uses clear diction
  • It develops timing and control

Practice Routine 

  • Start with breathing exercises
  • Practice long sustained notes
  • Work on smooth phrasing
  • Apply techniques to songs

Following a consistent singing routine will help you improve faster.

Common Mistakes to Avoid 

  • Breaking phrases too often
  • Singing too rigidly on the beat
  • Forcing your voice instead of staying relaxed

Improving your vocal strength will help you avoid strain and maintain control.

Final Thoughts 

 Learning how to sing like Frank Sinatra is about control, phrasing, and storytelling. By focusing on breath, timing, and expression, you can develop a smooth and confident singing style. 

Ready to Improve Your  Singing?

 If you want faster progress, working with a vocal coach can help you refine your technique and build confidence. 

About the author

Mike Elson

Mike Elson

Mike loves to sing and make magic happen with computers and music. After trying lots of ways that didn't work to find his head voice, his voice ended up broken and his concepts mixed up. 

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