Frank Sinatra was a famous singer known for his smooth voice and charming style. Many people loved his music, and he became very popular all around the world. Sinatra sang many songs that are still loved today. Did you know there are other singers who sing like him? In this article, we will talk about 25 male singers whose music and style remind us of Frank Sinatra. Some of these singers are from Sinatra’s time, and some are newer, but they all share something special with him. Let’s explore these singers and their wonderful songs. You might find some new favorites that make you think of Sinatra!
1. Feeling Good – Michael Bublé
Michael Bublé’s “Feeling Good” has become a signature song that showcases his ability to channel the essence of classic crooners like Frank Sinatra. The song, originally popularized by Nina Simone, takes on a fresh yet timeless quality in Bublé’s rendition, capturing the grandeur and soul of the classic with a modern touch. His powerful vocals and confident delivery bring a new layer of sophistication to this beloved standard, making it a favorite among fans of traditional pop and jazz.
Michael Bublé often cites Frank Sinatra as a major influence, and this is evident in his approach to music, focusing on big band arrangements and smooth, polished vocals. The song “Feeling Good” is featured prominently in Bublé’s live performances and has appeared in various advertisements and movies, further cementing its place in contemporary culture while paying homage to the musical greats of the past. This connection makes Bublé a perfect example of a modern-day artist following in Sinatra’s footsteps.
2. Come Fly With Me – Harry Connick Jr.
Harry Connick Jr. brings a lively charm to “Come Fly With Me,” a song that Sinatra made famous in the late 1950s. Connick’s version is infused with his New Orleans jazz roots and charismatic stage presence, making the classic tune feel both fresh and timeless. His ability to blend Sinatra’s swagger with his unique musical flair has earned him a spot as a modern-day crooner beloved by fans of traditional pop.
This song showcases Connick’s skillful piano play and vibrant orchestral arrangements, echoing the grandeur of Sinatra’s era while introducing his own artistic expression. It’s a staple in Connick’s performances, loved for its joyful energy and nostalgic pull.
3. Night and Day – Rod Stewart
Rod Stewart’s cover of “Night and Day” from the Great American Songbook series highlights his raspy, soulful voice against the backdrop of a lush orchestral arrangement. This song, which has been a standard for many artists, was interpreted by Sinatra with great success, and Stewart’s rendition pays homage while adding a touch of rock star charisma.
The song’s smooth melodies and Stewart’s distinctive voice create a bridge between classic pop and modern sensibilities, proving that great music truly is timeless. His interpretation brings a new texture to the song, demonstrating his versatility and respect for classic standards.
4. The Way You Look Tonight – Tony Bennett
Tony Bennett’s rendition of “The Way You Look Tonight” captures the romantic allure that Sinatra once delivered to his audience. Bennett’s performance is filled with warmth and tenderness, making it a beloved classic that resonates with those who appreciate the crooning style of the mid-20th century.
Bennett, like Sinatra, has a way of telling a story through music, bringing emotional depth and elegance to the lyrics. His interpretation is often considered a heartfelt nod to the days when Sinatra dominated the airwaves, continuing to enchant listeners with its classic appeal.
5. Mack the Knife – Bobby Darin
Bobby Darin’s “Mack the Knife” is a dynamic and powerful performance that showcases his flair for theatricality and vocal strength. This song, which became a signature hit for Darin, was also performed by Sinatra, but Darin’s version stands out with its youthful energy and bold swing influences.
The song has become synonymous with Darin’s name, often cited as one of the greatest recordings of the 20th century. His ability to capture the audience’s imagination and deliver a song with such vigor makes it a classic in the realm of swing and big band music.
6. My Way – Paul Anka
Paul Anka’s version of “My Way” is particularly noteworthy because he actually wrote the English lyrics to this iconic song, famously performed by Sinatra. Anka’s own rendition brings a personal touch and depth, emphasizing the song’s themes of reflection and independence. His delivery is smooth and commanding, reminiscent of Sinatra’s, but with a distinctively Anka twist.
This song has been covered by many artists, but Anka’s version stands out for its authenticity and the emotional connection he brings, making it a powerful homage to the spirit of Sinatra’s music.
7. Ain’t That a Kick in the Head – Dean Martin
Dean Martin, a close contemporary and friend of Sinatra, delivers “Ain’t That a Kick in the Head” with his trademark easy-going charm and warm vocal style. This song exemplifies the Rat Pack era’s cool and suave demeanor, with Martin’s performance oozing the effortless cool that was Sinatra’s hallmark too.
Martin’s rendition is playful and breezy, capturing the essence of the carefree and glamorous lifestyle that the Rat Pack portrayed. It’s a quintessential piece that showcases the enduring appeal of this genre.
8. Fly Me to the Moon – Jack Jones
Jack Jones offers a splendid version of “Fly Me to the Moon,” a song that Sinatra famously covered in his inimitable style. Jones’ interpretation is filled with lush orchestration and a vocal delivery that’s both powerful and nuanced, making it a standout among classic interpretations of this beloved standard.
The song’s romantic and dreamy lyrics are perfectly suited to Jones’ vocal range and emotional expression, creating a version that is both respectful of Sinatra’s influence and distinctly his own.
9. Autumn Leaves – Nat King Cole
Nat King Cole’s “Autumn Leaves” is a masterful interpretation of a jazz standard that Sinatra also performed. Cole’s version stands out for its delicate phrasing and exquisite vocal control, which convey deep emotion and a poignant sense of longing. His piano playing adds an additional layer of sophistication and depth to the song.
Cole’s ability to connect with his audience through music is evident in this performance, making “Autumn Leaves” a timeless piece that resonates with listeners who appreciate the depth of classic vocal jazz.
10. You Make Me Feel So Young – Barry Manilow
Barry Manilow’s take on “You Make Me Feel So Young” captures the youthful joy and exuberance that Sinatra brought to the original. Manilow’s performance is lively and spirited, filled with an infectious enthusiasm that makes the song feel both classic and contemporary.
His flair for dramatic presentation and his ability to connect with the emotional core of the song make his version a vibrant tribute to the enduring legacy of Sinatra’s music.
11. Witchcraft – Elvis Costello
Elvis Costello’s “Witchcraft” brings a unique twist to a song that Sinatra famously infused with charm and a touch of seduction. Costello, known for his eclectic style, interprets the song with a slightly edgier tone, mixing traditional pop with his characteristic new-wave influence.
This rendition highlights Costello’s versatility as an artist and his ability to adapt and respect classic tunes while infusing them with his personal artistic identity. It’s a fresh take on a classic that pays respect to Sinatra’s stylings while showcasing Costello’s own musical prowess.
12. All of Me – John Legend
John Legend’s “All of Me” is a modern classic that echoes the deep emotional expression found in Sinatra’s ballads. While not stylistically identical, Legend’s powerful vocal delivery and heartfelt lyrics resonate with the kind of intense sentiment that Sinatra conveyed in his most memorable performances.
This song has captivated a global audience, showcasing Legend’s skill as a songwriter and his ability to connect deeply with listeners, much like Sinatra did in his time.
13. Summer Wind – Michael Bolton
Michael Bolton’s version of “Summer Wind,” a song Sinatra turned into a summer anthem, showcases Bolton’s emotive vocal style and his ability to convey a sense of nostalgia and longing. Bolton’s powerful voice brings a new intensity to the song, making it resonate with those who appreciate robust vocal performances.
His rendition maintains the song’s classic feel while adding his own signature style, making “Summer Wind” a bridge between Sinatra’s era and contemporary musical interpretations.
14. It Was a Very Good Year – James Taylor
James Taylor’s gentle and thoughtful interpretation of “It Was a Very Good Year” brings a folk-infused sensibility to a song that Sinatra immortalized with his reflective and melancholic rendition. Taylor’s version highlights his distinctive vocal style and acoustic guitar play, offering a softer, more introspective take on the classic.
This song fits beautifully within Taylor’s body of work, known for its emotional depth and soothing melodies, and adds a unique perspective to a song often associated with Sinatra’s more orchestral arrangements.
15. The Lady is a Tramp – Jamie Cullum
Jamie Cullum’s energetic rendition of “The Lady is a Tramp” infuses the classic with a modern jazz twist, showcasing his dynamic piano skills and charismatic vocal delivery. This song, a favorite of Sinatra’s, is reimagined by Cullum in a way that stays true to the original’s playful and rebellious spirit while introducing his own vibrant energy and contemporary jazz influences.
Cullum’s performance is a testament to the lasting appeal of this song, appealing to both traditional fans of the genre and younger audiences who appreciate the fusion of classic and modern musical elements.
16. Cheek to Cheek – Seth MacFarlane
Seth MacFarlane’s rendition of “Cheek to Cheek” brings a surprising touch of classic Hollywood to his jazz vocal performance. Known more widely for his work in television and film, MacFarlane shows a deep appreciation for the Great American Songbook, channeling the smooth and suave demeanor that Sinatra perfected. His voice elegantly carries the tune with a timeless quality that reminds listeners of the golden age of crooners.
MacFarlane’s performance not only pays homage to Sinatra but also proves his versatility and genuine passion for this style of music, making “Cheek to Cheek” a delightful and polished tribute.
17. Blue Moon – Chris Isaak
Chris Isaak’s “Blue Moon” captures the melancholic and soulful essence of the classic song that Sinatra also famously interpreted. Isaak’s version features his signature smooth, haunting voice paired with a minimalistic arrangement that allows his vocal performance to shine through. This approach brings a fresh and intimate perspective to the song, highlighting its emotional depth.
Isaak’s ability to connect with the core sentiments of the song, combined with his unique stylistic flair, makes his version a memorable addition to the list of artists influenced by Sinatra’s musical legacy.
18. New York, New York – Robbie Williams
Robbie Williams’ cover of “New York, New York” is a dynamic and theatrical performance that channels Sinatra’s larger-than-life persona. Williams brings his own pop-star charisma to the classic, infusing it with energy and a modern vibe that resonates with today’s audiences. His rendition is both a tribute and a personal reinterpretation, filled with the flair and spectacle that Robbie Williams is known for.
This song, emblematic of Sinatra’s connection to the spirit of New York City, is reinvigorated by Williams with a contemporary twist, making it appealing across generations.
19. Under My Skin – Michael Bublé
Michael Bublé returns to this list with his vibrant cover of “Under My Skin,” a song that Sinatra immortalized with his smooth and seductive delivery. Bublé’s modern crooner style perfectly suits this classic, allowing him to showcase his polished vocals and charismatic stage presence. His performance captures the timeless allure of Sinatra’s music while adding a fresh, contemporary feel.
Bublé’s version appeals to both long-time Sinatra fans and those new to the genre, bridging the gap with his accessible and engaging approach to these classic tunes.
20. Someone to Watch Over Me – Sting
Sting’s interpretation of “Someone to Watch Over Me” showcases his versatility as a musician, bringing a delicate and thoughtful approach to this Gershwin classic. His version is infused with a jazz sensibility that complements the song’s lyrical themes of longing and protection. Sting’s distinctive voice adds a layer of complexity and modernity to the tune, making it resonate with a contemporary audience while maintaining its classic charm.
The arrangement’s subtle orchestration allows Sting’s vocal nuance to shine, presenting a sophisticated and heartfelt rendition that honors Sinatra’s emotional depth.
21. Strangers in the Night – Barry Manilow
Barry Manilow’s version of “Strangers in the Night” revisits the romantic and mysterious vibe of the song Sinatra famously turned into a worldwide hit. Manilow’s smooth, emotive performance adds a layer of contemporary polish while staying true to the song’s original feel. His ability to convey the song’s narrative about a fleeting, chance encounter that turns into lasting love captures the essence of the classic.
Manilow’s interpretation is both nostalgic and fresh, appealing to those who remember the original and those discovering it for the first time.
22. Luck Be a Lady – Seal
Seal’s cover of “Luck Be a Lady” brings his distinctive, soulful voice to one of Sinatra’s most iconic tunes. Known for his deep, rich tone, Seal adds a modern R&B flair to the song, making it feel both classic and contemporary. His version is dramatic and commanding, with a powerful delivery that gives the song a new, vibrant energy.
This rendition is a perfect example of how timeless music can be reinterpreted through different musical styles and voices, connecting with audiences across different eras.
23. Moonlight Serenade – Kurt Elling
Kurt Elling’s “Moonlight Serenade” is a beautifully crafted jazz interpretation that highlights his exceptional vocal range and control. This song, which Sinatra also performed beautifully, is delivered by Elling with a fresh jazz twist, incorporating his renowned improvisational skills and emotional depth. His version is both respectful of the original and innovative, showcasing his talent as one of the leading voices in modern jazz.
Elling’s rendition brings a new dimension to the song, appealing to jazz aficionados and casual listeners alike with its sophisticated and captivating style.
24. That’s Life – Shawn Mendes
Shawn Mendes brings a youthful spirit and contemporary pop sensibility to “That’s Life,” a song that Sinatra turned into an anthem of resilience. Mendes’ version is energetic and heartfelt, featuring his signature pop style that makes the classic tune accessible to a younger audience. His fresh take on the song retains its powerful message of facing life’s ups and downs with determination and optimism.
This reinterpretation connects the generational gap, showing that the themes in Sinatra’s music are timeless and resonate universally.
25. Everybody Loves Somebody – Dean Martin
Dean Martin, another Rat Pack member closely associated with Sinatra, shines with his rendition of “Everybody Loves Somebody.” This song, which Martin made his signature tune, echoes the smooth and charming style of Sinatra, but with Dean’s own laid-back, velvety vocals. His performance is filled with warmth and an inviting tone that made it a hit and a classic in its own right