30 Best Frank Sinatra Songs on YouTube: The Ultimate Playlist

1. My Way - My Way (Expanded Edition)

My Way

Artist: Frank Sinatra

Vocal Performance: Sinatra's iconic baritone voice delivers a powerful and emotionally resonant performance, perfectly conveying the song's themes of defiance and reflection. His phrasing is impeccable, making every word resonate with meaning.

YouTube Appeal: The song's enduring popularity and powerful message ensures high engagement on YouTube, making it a natural choice for playlists showcasing Sinatra's best work. The video's likely inclusion of compelling visuals will further enhance its appeal.

Timeless Quality: "My Way" transcends generations, remaining relevant due to its universal themes of self-acceptance and looking back on life, making it a perfect addition to any "Best of Sinatra" YouTube compilation.

2. Fly Me To The Moon

Sinatra's Vocals: Frank Sinatra's velvety smooth baritone shines, delivering a performance that's both intimate and powerful, perfectly showcasing his phrasing and emotional control.

Count Basie's Arrangement: Basie's big band arrangement provides a lush, swinging backdrop that perfectly complements Sinatra's vocals, creating a timeless and effortlessly cool sound.

YouTube Appeal: This classic rendition is instantly recognizable and highly shareable, making it a perfect addition to any "Best of Sinatra" YouTube playlist.

3. That's Life

Vocal Performance: Sinatra's masterful delivery of "That's Life" showcases his unparalleled vocal control and emotional depth, perfectly capturing the song's bittersweet sentiment.

Musical Arrangement: The memorable arrangement, featuring a driving rhythm and lush orchestration, provides a dramatic backdrop to Sinatra's vocals, enhancing the song's impact.

YouTube Appeal: The timeless quality and emotional resonance of "That's Life" make it a perfect choice for YouTube playlists celebrating Sinatra's best work, ensuring high viewership and engagement.

4. The Way You Look Tonight (Frank Sinatra - 1964)

Vocal Performance: Sinatra's velvety smooth vocals are iconic, perfectly capturing the romantic longing in "The Way You Look Tonight" His phrasing is impeccable, making every word resonate with emotion.

Timeless Melody: The song's melody is instantly recognizable and incredibly catchy, a testament to its enduring appeal. It's a tune that sticks with you long after the song ends, making it perfect for adding to your Frank Sinatra YouTube playlist.

Orchestral Arrangement: The lush orchestral arrangement complements Sinatra's voice beautifully, creating a rich and romantic atmosphere. The subtle instrumental details enhance the song’s emotional depth, making it a truly captivating listening experience for any Sinatra fan.

5. New York, New York

Vocals: Frank Sinatra's iconic vocal performance is a masterclass in phrasing and emotional delivery, perfectly capturing the song's yearning and celebratory spirit.

Big Band Sound: The lush orchestration and driving rhythm create an undeniably energetic and captivating listening experience, ideal for YouTube playlists focused on classic Sinatra.

YouTube Appeal: Its instantly recognizable melody and upbeat tempo make "New York, New York" a highly shareable and engaging track for a Frank Sinatra best-of compilation on YouTube.

6. I've Got You Under My Skin (1956)

I've Got You Under My Skin

Artist: Frank Sinatra

Vocal Performance: Sinatra's velvety smooth vocals and impeccable phrasing make this a quintessential example of his mastery.

Unforgettable Melody: The song's instantly recognizable melody is both haunting and captivating, ensuring its place in popular culture.

YouTube Appeal: Its timeless quality and enduring popularity make it a perfect addition to any "Best of Sinatra" YouTube playlist, guaranteeing high engagement.

7. Strangers In The Night (Frank Sinatra - 1966)

Vocals: Sinatra's velvety smooth baritone is in peak form, delivering the lyrics with effortless charisma and a touch of melancholy that perfectly encapsulates the song's theme of fleeting encounters.

Arrangement: The iconic instrumental arrangement, featuring a memorable melody and subtle string orchestration, creates a sophisticated and timeless soundscape that complements Sinatra's vocal performance, making it perfect for YouTube listening.

Emotional Resonance: "Strangers in the Night" evokes a sense of bittersweet romance and longing, making it a highly relatable and emotionally resonant choice for any Sinatra playlist curated for a YouTube audience.

8. You Make Me Feel So Young - Songs For Swingin' Lovers! (Remastered)

Vocals: Frank Sinatra's smooth, velvety baritone is in peak form on "You Make Me Feel So Young" showcasing his impeccable phrasing and effortless delivery that's perfect for a YouTube playlist.

Swing Rhythm: The song's infectious swing rhythm is undeniably catchy and makes it incredibly easy to listen to and enjoy repeatedly; ideal for building a relaxing yet upbeat YouTube experience.

Timeless Appeal: Its classic arrangement and universally relatable theme of youthful romance ensure this track remains a staple for Sinatra fans and newcomers alike, making it a great addition to any "best of" YouTube compilation.

9. Come Fly With Me

Vocals: Frank Sinatra's smooth, velvety baritone is in peak form on "Come Fly With Me" showcasing his unparalleled phrasing and effortless delivery.

Swing Rhythm: The song's infectious swing rhythm makes it perfect for a relaxing yet upbeat listening experience, ideal for YouTube background listening.

Nostalgic Vibe: Its sophisticated orchestration and romantic lyrics evoke a classic, timeless feel, enhancing its appeal on YouTube playlists dedicated to Sinatra's best works.

10. Moon River (1964)

Sinatra's Vocals: Frank Sinatra's velvety smooth baritone voice perfectly captures the melancholic yet hopeful essence of "Moon River" making it a truly iconic performance easily found on YouTube.

Lyrical Beauty: The poignant lyrics, evocative of dreams and longing, resonate deeply with listeners, contributing to the song's enduring popularity and making it a staple in many "Best of Sinatra" YouTube playlists.

Timeless Melody: The unforgettable melody is instantly recognizable and effortlessly blends with Sinatra's delivery, ensuring "Moon River" remains a captivating listen for generations, easily searchable and enjoyable on YouTube.