The 10 Best Frank Sinatra Songs of All-Time

Frank Sinatra

In the 1940s, Frank Sinatra swayed his way into the hearts of music lovers everywhere. His popularity may have peaked and waned in the years that followed, but he remained, and remains, one of the most enduringly popular singers of the 20th century. From his love songs to his Christmas music to his general talent as a singer, he is not a rock star or a hip-hop star like today’s stars, but he’s the most iconic.  Today, his music resonates just as strongly as ever. Here, we pay tribute to the finest interpreter of the Great American songbook of all time as we count down the 10 best Frank Sinatra Songs.

10. Mama Will Bark


“Ow, you out there/This is for keeping me awake every night, hah/ Well, take that! Yelp! And take that. Yelp. And take that. Yelp. Yelp, yelp, yelp, yelp, yelp, yelp. Hot dog, woof.” Yes, those really are the lyrics, and yes, the Huff Post really has named Mama Will Bark as one of the best Sinatra songs all time. If you think it’s a joke, listen to the song and tell me that croon doesn’t make you go puppy-eyed. Hot dog, indeed.

9. Bim Bam Baby


Sinatra had a knack for taking the most inane lyrics possible and transforming them into something wonderful. He did it more times than we can count, but never quite so masterfully than on Bim Bam Baby. Who else but the blue-eyed charmer could infuse quite so much passion into “Hey now, take a mip mack mop, and a brim bram broom/And klim klam clean up the rim ram room/ Cause your bim bam baby`s coming home tonight?” It might be a novelty song, but it’s no joke.

8. Have Yourself A Merry Little Christmas


Christmas and Frank Sinatra go together like love and marriage. Not to include at least one of his seasonal classics on our list would be akin to pulling Santa’s beard off. And Have Yourself A Merry Little Christmas is a very, very good song. First sung by Judy Garland on the “Meet Me In St. Louis” movie soundtrack, Sinatra initially covered it in 1948, replacing Garland’s sweet vocals with a honeyed croon that would have done Bing Crosby proud. Nine years later, he revisited the song to record what’s widely regarded as the definitive version for the 1957 album, Single.

7. New York, New York


No end of artists have had a crack at New York, New York, from Liza Minelli (for whom it was actually written) to Shirley Bassey. But only Frank Sinatra sang it so good, you’d want to listen to it twice. Released on the 1980 triple album Trilogy: Past, Present and Future, it was fundamental to reawaking the public interest in Sinatra and thrusting him firmly back into the limelight.

6. Something Stupid


On Something Stupid, we get two Sinatras for the price of one. Nancy’s own pop career was already in full swing when she cozied up to her dad on this 1967 No.1 hit, and her confident delivery and sweet vocals are more than a match for Frank’s. Even the diabolical Robbie Williams and Nicole Kidman version couldn’t tarnish its legacy.

5. My Way


By the late ’60s, Sinatra was several decades into his career and singing to a very different world to the one he’d started out in. But there was still a place for an old crooner, especially if that old crooner had a song like My Way up his sleeve. My Way may lack the strut and swagger of his Rat Pack days, but as All Music notes, it’s reflective, knowing arrangements show that Sinatra could master the middle ground between the rock that was dominating the charts and the swinging pop he’d built his career on. A smash hit on both sides of the Atlantic, it spent a staggering 75 weeks in the UK Top 40 and quickly became his signature song.

4. All of Me


Seven months after Songs for Young Lovers hit the shelves, Sinatra was back to doing what he did best on Swing Easy. Nelson Riddle was on hand to oversee the arrangements, and it’s him we have to thank for the masterful ebb and flow of the instrumentation. Things start gently enough, and then Sinatra reaches for the heavens with a vocal so soaring, it could make angels swoon. Never has a song about obsessive love sounded sweeter.

3. Come Fly With Me


As writes, the title track to Sinatra’s 1958 album Come Fly With Me perfectly captured the mood of America. World War II was in the past, and the country was looking to the future (and the skies) with more optimism than ever before. Buoyed along by Billy May’s artful arrangements and strutting saxes, it delivers a joyful piece of life-affirming swing.

2. I’ve Got You Under My Skin


Songs for Swingin’ Lovers! is a pitch-perfect album, and its highlight, I’ve Got You Under My Skin, is a slice of sheer swing perfection. Cole Porter composed the original, but after you hear Sinatra’s version, it’s impossible to imagine anyone else tackling it (although in fairness, Neneh Cherry’s hip-hop interpretation is worth a listen, even if it’s about as close to the original as chalk is to cheese).

1. I Get A Kick Out Of You


As The Guardian writes, Sinatra may have been the biggest musical star of the 1940s, but times change and so do tastes. By the early 1950s, the concert halls he’d once filled were now barely seated. The teeny boppers had moved on to fresh pastures, and swing was fast losing territory to something called ‘rock and roll.’ But then he signed to Capitol Records, and all of a sudden, Sinatra was everyone’s favorite blue-eyed boy again. I Get A Kick Out Of You is nothing short of superb, with Sinatra’s dreamy vocals and George Sirav’s pitch-perfect arrangements combining to create the ultimate love song.

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