How to Learn Singing “Winners” from Frank Sinatra

Learning to Sing “Winners” by Frank Sinatra

“Winners” is a masterpiece by Frank Sinatra that requires exceptional control and resonance. Sinatra was famed for his articulation, phrasing and sense of timing, aside from his unequivocal vibrato.

Identifying the Vocal Technique

Sinatra’s singing in “Winners” employs a technique often referred to as “legato”. This is a vocal style where each note is delivered smoothly and connected without any disruption to airflow. Mastering this technique requires an understanding of the basics of breath support and breathing techniques.

How to Master the Legato Technique

1. Understand Your Voice

Knowing your voice is crucial. If you haven’t done so already, take our Vocal Range Test to understand your voice better.

2. Warm-Up

Start with simple warm up exercises like humming or the 3 Minute Warm Up.

3. Breath Support

Ensure good breath support by following our guide on breath support and practicing exercises like the Farinelli Breathing.

4. Practice Legato

Start practicing legato on individual words or short phrases from the song using our Vocal Pitch Monitor. Gradually stitch together longer phrases as your legato improves.

5. Sing!

Once you’ve mastered these steps, it’s time to bring it all to the “Winners” song. Look for the song using our Song Search feature.

Common in Frank Sinatra’s Repertoire

The legato technique is a staple in Frank Sinatra’s singing. It’s particularly prominent in songs like “That’s Life,” “Strangers in the Night,” and “My Way”.


Learning to sing “Winners” by Frank Sinatra isn’t easy. However, with our resources supporting your practice, you’re far better equipped to nail Sinatra’s rendition on stage, in the shower, or anywhere else you sound great. Happy singing!