The Classic Crooners Cocktail Hour Playlist, Volume One

When it comes to Cocktail Hour music at a wedding reception, there may not be a more popular playlist than this Rat Pack Era inspired mix. There is just something timeless about listening to the soothing voices of Frank Sinatra, Ella Fitzgerald, Dean Martin, Etta James, Louis Armstrong, and other classical jazz vocalists, while sipping cocktails and mingling with family and friends. Whether your wedding’s theme is sophisticated, classy, traditional, timeless, or any combination of the aforementioned,  this Classic Crooners Cocktail Hour playlist will set the perfect mood and atmosphere.

Fun Fact: Originally, “Crooner” was a term used to describe a male singer who sang sentimental songs in a soft, low voice. Over time, Crooner morphed into a term used to describe singers of jazz standards, who are backed by either a full orchestra, a big band, or a piano.

Tony’s Classic Crooners Cocktail Hour Drink of Choice: Easy. When I think Crooners, I think tailored suits, cuff links, Rolex watches, cigars, and mingling with guests while sipping an Old Fashioned. Enjoy my selections, and as always, the full Spotify playlist is available at the end!

The Classic Crooners Cocktail Hour Playlist

Frank Sinatra – “Come Fly With Me”  |  PURCHASE: Amazon MP3
It only made sense that I started off this Crooners playlist with one of Frank’s most streamed songs on Spotify.

Bobby Darin – “Mack The Knife”  |  PURCHASE: Amazon MP3

Dean Martin – “Ain’t That A Kick In The Head”  |  PURCHASE: Amazon MP3
With popular Crooners like Frank and Dean, the trick is to space their songs out as much as possible. Dean makes his first appearance on the playlist with his most popular song on Spotify.

Peggy Lee – “Fever”  |  PURCHASE: Amazon MP3
The Modern Crooners Cocktail Hour Playlist would include Michael Bublé’s rendition.

Ella Fitzgerald & Louis Armstrong – “Cheek To Cheek”  |  PURCHASE: Amazon MP3

Louis Prima – “Pennies From Heaven”  |  PURCHASE: Amazon MP3
I love to play this song. It never gets old or tiresome.

Etta James – “Something’s Got A Hold On Me”  |  PURCHASE: Amazon MP3
And now you know what song Flo Rida and Avicii sampled for their respective hits.

Frank Sinatra – “Yes Sir, That’s My Baby”  |  PURCHASE: Amazon MP3

Sammy Davis, Jr. – “Something’s Gotta Give”  |  PURCHASE: Amazon MP3

Louis Armstrong – “La vie en rose”  |  PURCHASE: Amazon MP3
Lady Gaga performed this in the 2018 movie “A Star is Born” and SLAYED it. But since this is a Classic Crooners playlist, Louis Armstrong gets the nod.

Nina Simone – “Feeling Good”  |  PURCHASE: Amazon MP3

Bobby Darin – “Beyond The Sea”  |  PURCHASE: Amazon MP3

Vic Damone – “Let’s Fall In Love”  |  PURCHASE: Amazon MP3

Tony Bennett – “I Can’t Believe That You’re In Love With Me”  |  PURCHASE: Amazon MP3



Ella Fitzgerald – “Ev’rything I’ve Got”  |  PURCHASE: Amazon MP3

Lena Horne – “Honeysuckle Rose”  |  PURCHASE: Amazon MP3

Nat King Cole – “Orange Colored Sky”  |  PURCHASE: Amazon MP3

Frank Sinatra – “Fly Me To The Moon (In Other Words)”  |  PURCHASE: Amazon MP3
As of last check, this song is Frank’s most streamed song on Spotify by far.

Louis Prima – “When You’re Smiling/The Sheik of Araby”  |  PURCHASE: Amazon MP3

Etta James – “I Just Want To Make Love To You”  |  PURCHASE: Amazon MP3
I really love the vocals of this song and the aforementioned Nina Simone song, “Feeling Good”. 

Dean Martin – “Sway (Quien Sera)”  |  PURCHASE: Amazon MP3

Perry Como – “Papa Loves Mambo”  |  PURCHASE: Amazon MP3

Rosemary Clooney – “Mambo Italiano”  |  PURCHASE: Amazon MP3
I have absolutely ZERO clue what this song is about. But it is nonetheless awesome and the perfect setup for the next song.

Dean Martin – “That’s Amore”  |  PURCHASE: Amazon MP3
Obviously, save it for later if you need to.

Fred Astaire – “Puttin’ On The Ritz”  |  PURCHASE: Amazon MP3
Fun Fact: A one-hit wonder artist named Taco did a version of this song in the 80s that spawned a couple of remixes that were supa dupa.

Marilyn Monroe – “Diamonds Are A Girl’s Best Friend”  |  PURCHASE: Amazon MP3

Frank Sinatra – “I’ve Got The World On A String”  |  PURCHASE: Amazon MP3

Nat King Cole – “L-O-V-E”  |  PURCHASE: Amazon MP3
I love to go out with a bang, and playing this classic by Nat King Cole has an epic ending that is perfect for concluding the Cocktail Hour and allowing me to introduce the next segment of formalities before dinner begins.

The Classic Crooners Cocktail Hour Playlist


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