How to Learn Singing “My Funny Valentine” from Frank Sinatra

Frank Sinatra’s iconic rendition of “My Funny Valentine” offers a masterclass in the art of storytelling through music. This guide will help you learn how to sing this song much like the master crooner himself.

Understanding the Song

You need to understand your song before you can effectively portray it. First, listen to Sinatra’s version carefully, noting the emotional nuances and storytelling aspects of his performance. The story told in this song should guide your vocal choices.

Vocal Techniques

Chest Voice

“My Funny Valentine” primarily employs the vocal register known as the chest voice. Make sure to use our Singing Comfort Zone video to familiarize yourself with this register.


Frank uses a technique known as “twang” to add a unique character to his voice. Enhance your “twang” with this exercise. Johnny Cash’s “Ring of Fire” and Elvis Presley’s “Hound Dog” also use this technique.


Sinatra mildly employs vibrato in longer note durations. Practice this technique using the Beggars Bounce and Diaphragm Bounce exercises.

Delivery and Articulation

Clear articulation combined with Sinatra’s smooth delivery style is key. Sinatra uses relaxed articulation to make the lyrics flow, projecting a natural and conversational style in his singing. Practice relaxed articulation using the Finger Bite exercise.

Pitch and Key

Use the pitch accuracy test to check your accuracy and review our article on voice types to find the right key for your voice.

Emotion and Performance

Remember to tell the story behind the song, share its emotions and perform with authenticity. You can learn more about this in Singing with Intuition, Skills, Emotion, and Thinking.

Final Tip

Singing Sinatra’s “My Funny Valentine” may seem like a tall task, but with practice and dedication, you’ll be able to put your spin on this classic. Be sure to warm up using one of our warm-up routines before each practice session!

So go ahead, step into your practice studio and start singing!