Bing Crosby
what is Bing Crosby's best-selling single of all time and a perennial holiday favorite?
White Christmas
One of Como's signature songs, it won him the 1958 Grammy Award for Best Male Vocal Performance and remains one of his most recognizable tunes.
Catch a Shining Star
Perhaps Sinatra's most iconic song, known worldwide as his signature tune, epitomizing his style and career philosophy.
My Way
Perhaps Dean Martin's most iconic song, captures his charismatic and playful style perfectly. It became a massive hit after appearing in the 1953 movie "The Caddy."
That's Amore
This song became Tony Bennett's signature tune and won him multiple Grammy Awards.
I Left My Heart In San Francisco
This song is one of Crosby’s most memorable hits, known for its whimsical and light-hearted lyrics.
Pennies from Heaven
A fun and upbeat song that highlights Como's ability to handle more rhythmic tunes, showcasing a different side of his musical range.
Papa Loves Mambo
An anthem for New York City that became synonymous with Sinatra, celebrated for its energetic and triumphant tone.
New York, New York
This song became a signature tune for Martin, even replacing "That's Amore" as the theme on his TV show. It hit number one on the Billboard chart in 1964, showcasing his enduring appeal.
Everybody Loves Somebody
Another major hit for Bennett, this song exemplifies the dramatic range and vocal power he brings to his performances.
Rags to Riches
A duet with The Andrews Sisters that became an anthem of personal freedom and showcased Crosby's versatility.
Don't Fence Me In
This song was a big hit in the early 1970s, showing Como's staying power as a top vocalist well beyond his initial peak in popularity.
It's Impossible
A huge commercial hit for Sinatra, this song won him multiple Grammy Awards and features one of his most memorable melodic lines.
Strangers In The Night
Known in Italian as "Nel blu dipinto di blu," this song was a staple in Martin's repertoire, celebrated for its lively tempo and evocative lyrics.
Volare
Tony Bennett’s version of this Charlie Chaplin song
Smile
A spirited rendition of the Irving Berlin classic that showcased Crosby's ability to handle both jazz and pop with ease.
Alexander's Ragtime Band
From the musical "South Pacific," Como's version is one of the most loved renditions of this Rodgers and Hammerstein classic.
Some Enchanted Evening
A Cole Porter song that Sinatra made his own with a memorable arrangement by Nelson Riddle, widely considered one of his best recordings.
I've Got You Under My Skin
Featured in the 1960 film "Ocean's 11," this song is synonymous with the Rat Pack's swagger and has been used in numerous movies and TV shows since.
Ain't That a Kick in the Head
This love theme from "The Sandpiper" film is one of Bennett's most romantic performances, filled with longing and nuance.
The Shadow of Your Smile
This song won an Academy Award for Best Original Song and remains one of his most famous and catchy tunes.
Swinging on a Star
Based on Chopin's Polonaise in A-flat major, this song became a huge hit in the 1940s and helped cement Como's status as a major star.
Till The End of Time
Sinatra’s rendition brought a playful and stylish edge to this Rodgers and Hart song from the musical "Babes in Arms."
The Lady Is A Tramp
A beloved song that epitomizes Martin's smooth and romantic style, often featured in his live performances.
You're Nobody till Somebody Loves You
A song that became synonymous with Bennett’s philosophy of savoring life’s pleasures, it's a staple in his repertoire.
The Good Life