Best Dean Martin Songs: The Greatest Songs by The Great Entertainer

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Last updated on June 1st, 2023 at 09:30 pm

Dean Martin was known as the “King of Cool,” releasing 32 studio albums throughout his more than 60-year career.

This best-selling entertainer never shied away from his Italian roots in his classic songs, both as originals and covers, and he’s the icon of the romantic love song.

How could we choose our favorites from this beloved film star, singer, and Rat Pack alum, who is so popular that he was honored with a Grammy Lifetime Achievement Award? We don’t know, but we did.

Here’s our list of the 16 Best Dean Martin Songs to add to your best of the 1950s and 1960s playlist.

16. “Little Ole Wine Drinker, Me”

“Little Ole Wine Drinker, Me” may be a country-pop song by trade, but the “King of Cool” crooner embraced it when he released it in 1967.

As the narrator tries to drink away his romantic troubles, we cannot help but relate to the need for a glass of wine when we’re having romantic problems.

15. “The Door is Still Open to My Heart”

Like so many others to come on our list of the best Dean Martin songs, “The Door is Still Open to My Heart” might not have been originally his, but his is the one that everybody still remembers most.

It spent 11 weeks on the Billboard Hot 100 chart, peaking in the Top 10 at number six overall.

This song is the perfect sentiment of how the right person seems to be the one that completes us, and all we want to do is for them to know it and be right by our side.

The door will always be open to our hearts for this song to come through.

14. “Under the Bridges of Paris”

So many of the best Dean Martin songs take us to his roots in Italy, but he does just as stellar of a job taking us to another romantic city with “Under the Bridges of Paris.”

It’s the more romantic version of going under the bleachers at the football stadium, and even if it didn’t chart in the United States, we love listening to it with our significant other on a date night.

13. “Baby It’s Cold Outside”

This famous duet may have received some backlash in recent years because of a world that’s getting a little too sensitive about some things, but it’s still a classic Christmas tune in the era of Dean Martin.

We find this call-and-response duet charming as the man tries to persuade the woman to stay. Despite whatever innuendos people think is happening, it’s clear the woman isn’t distressed and seems willing to remain in his company.

Martin brought this classic duet alive with many, his most famous being with Marilyn Maxwell.

In 2006, Martina McBride brought Martin’s classic crooning sound back to our living rooms as she recorded the song for re-releasing her White Christmas album.

12. “On an Evening in Roma”

Who doesn’t have it on their bucket list to visit Rome with their lover someday?

Dean Martin gives us a peak into that dream vacation with his 1959 song, “On an Evening in Roma.”

With the perfectly descriptive song of the city’s magic, we know the fun has just begun when the sun goes down, and we can’t wait to experience an evening in Roma someday, too.

11. “You Belong to Me”

Originally written as a story about a woman pleading with her man serving overseas in World War II not to forget her, it is ultimately a universal song about the pain of being separated from a lover, no matter what the reason may be.

Martin covered “You Belong to Me” in 1952, and his version peaked at number 12 on the charts and remained charted for 10 weeks.

His version, with many others combined, earned it a number-one spot on the Cash Box charts.

No matter what, Martin’s version of this beautifully done song is the one we’ll always choose to play first.

10. “Let it Snow! Let it Snow! Let it Snow!”

Bing Crosby was famed for making “White Christmas,” the classic Christmas tune it is today. Dean Martin did the same with “Let it Snow! Let it Snow! Let it Snow!”

His 1959 version of the song for his A Winter Romance album was the most popular at the time, even beating out legendary crooner Frank Sinatra’s 1950 version.

Although it hasn’t received the critical acclaim that “White Christmas” has, Martin’s version of this lighthearted song broke the Top 10 on three different U.S. charts and multiple other countries, too.

This song was on fire and so delightful that we’ll sing “Let it Snow! Let it, Snow! Let it Snow!” all year long if it means putting this favorite of all the Christmas songs on repeat, especially on Christmas Day when we can pay tribute to the Italian American singer.

9. “Mambo Italiano”

Dean Martin followed in the footsteps of the beautiful Rosemary Clooney for his 1955 cover of “Mambo Italiano.”

His version was so popular that it was featured in a 2022 commercial for Airbnb, and it only made us want to listen to it over and over when we booked our next vacation spot.

8. “Volare”

“Volare” is one of our favorite Dean Martin songs to bop along to. It’s a timeless classic, first released by Martin in 1958, and although we may not know what he’s saying for half the song, we can’t help but be captivated by his smooth delivery of the song.

7. “Sway”

We know we’re about to hear something special when we hear that classic Italian rhythm begin.

Dean Martin first released his hit song, “Sway,” in 1954, and it immediately made us want to find that person we can’t get enough of and dance with them.

For that, it’s got to be one of the best Dean Martin songs out there.

6. “Memories are Made of This”

Feeling nostalgic? Then you couldn’t make a better selection than to queue up Dean Martin’s 1955 song, “Memories are Made of This.”

Backed by The Easy Riders, Dean Martin earned a number-one hit for this classic that would become one of his most prominent recordings ever, both in the United States and the United Kingdom.

The song has made its mark in culture as well. It was so popular that Ida Boros covered the song during the 1956 Hungarian Revolution as an “unofficial anthem for refugees scattered around the world.”

Bring your lips with mine after we sip on some wine, and we’ll make memories from this classic song all the live long day.

5. “Return to Me”

Dean Martin’s voice is absolutely captivating in this top-five hit.

In “Return to Me,” the narrator pleads with the one he loves whom he has lost, begging her to forgive him if he has wronged her and to hurry home to his heart.

Martins shows off his Italian heritage in this beautifully done song and makes us only wish that he was calling us “Bella Mia” and begging for us to be the ones to come back home to his arms, his lips, and his heart.

4. “Ain’t That a Kick in the Head”

This swinging big band jazz arrangement released by Dean Martin, featuring Nelson Riddle, in 1960 has to be one of the best we’ve ever heard.

“Ain’t That a Kick in the Head” was initially written by Jimmy Van Heusen and Sammy Cahn for the Ocean’s 11 films that would be released later that year, but Martin’s version of the song came out a month before the movie debuted.

Although this catchy song did get charted at first, it has continued to keep its life as it’s included on many of the beloved singer’s Greatest Hits compilation albums.

It also has seen quite a bit of play in the video game world, featured in games such as Fallout New Vegas and Mafia II.

3. “You’re Nobody till Somebody Loves You”

Dean Martin might not have been the original artist on this hit song, but he is the one who made it most popular.

Written in 1944 by Russ Morgan, Larry Stock, and James Cavanaugh, this classic song reminds people everywhere that having somebody to love is more precious than anything else.

Martin’s version spent nine straight weeks on the charts in 1964, so go “find yourself somebody to love” while we queue up this song again. Maybe we’ll even watch his performance of it on his comedy-variety show, The Dean Martin Show!

2. “Everybody Loves Somebody”

Make no mistake, “Everybody Loves Somebody” is Dean Martin’s song. It may have already been written and out in the world for 20 years when he finally released it in June 1964, but his is the only one that’s worth remembering.

By the time he released it featuring a full orchestra, Martin had spent the previous six years without a top 40 hit on the charts thanks to the popularity of many British groups at the time, including the Beatles.

His son, Dean Paul Martin, who was 12 at the time, was a fan of the popular group, which Dean Martin resented because of his dislike for rock-and-roll.

He would famously tell his son, “I’m gonna knock your pallies off the charts,” and he did when “Everybody Loves Somebody” replaced The Beatles’ “A Hard Day’s Night” for the number-one spot on Aug. 15, 1964.

If there’s any song worthy of that honor, it’s this one, as it became one of the most signature Dean Martin songs of the time.

1. “That’s Amore”

We love it so much when this classic artist returns to his Italian roots, which is why we think “That’s Amore” is the best of the Dean Martin songs.

The work of composer Harry Warren and lyricist Jack Brooks, “That’s Amore” is “a charming, if goofy, parody of popular Neapolitan organ-grinder music,” according to Joe Queenan, a famed music critic.

He also said the sensual song is “one of many songs from the early fifties that helped rehabilitate Italy’s image as a land of magic and romance that had somehow been lured from its festive moorings by the glum fascist Benito Mussolini.”

This classic song is the perfect embodiment of the romance of Italy from the big pizza pie when the moon hits the eyes, and the world seems to shine, well, you know the rest.

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