Personally I really like How High the Moon by Les Paul and Mary Ford.

Hard to choose just one favorite, but one tune that often tickles my brain is "In The Still Of The Night", by the 5 Satins. Another would be "Blue Tango", by Les Baxter.

I like most songs fron 1930 to today.
My grandfather love Western songs for 1950's I did not till 1970's. There are a few from 1950 to today.

Dave

That's a tough one. I think Blue Suede Shoes by Carl Perkins is right up there, though .

That's an eternity in popular music! But I especially like "Since I Don't Have You" by Jimmy Beaumont and the Skyliners. A hometown boy.

I wouldn't turn down a chance to listen to "When Sunny Gets Blue" by Johnny Mathis, or "Dream" by the Pied Pipers, or "Out of Nowhere" by Bing Crosby. Then there are the movie soundtracks and Broadway shows. An embarrassment of riches!

How can you pick just one?

You can't.

The playlist for the Netflix movie "The Irishman" covers that era pretty well.

"In the Still of the Night", top of the list, plays during the movie and for the closing credits. "Sleepwalk" is good, sets the mood. Lots of favorites. Robbie Robertson wrote the original score for the movie and I imagine chose many or all of the tunes. Martin Scorcse directed, stars DeNiro, Pacino, and Pesci.
Check it out and watch for the 1959 Zenith C-845 or similar, DeNiro and Pesche meeting around a table with Tony Salerno. The black Hudson Hornet is something to see too. Pacino is a loud belligerent Jimmy Hoffa. Pesci doesn't know a timing chain from a Chev timing Gear, oh well, he's a good gangster kingpin.

Here's the list of great tunes:

“In the Still of the Night� – The Five Satins
“Tuxedo Junction� – Glenn Miller & His Orchestra
“I Hear You Knockin’� – Smiley Lewis
“The Fat Man� – Fats Domino
“El Negro Zumbón (From the Motion Picture Anna)� – Flo Sandon’s
“Le Grisbi� – Jean Wetzel
“Delicado� – Percy Faith & His Orchestra
“Have I Sinned� – Donnie Elbert
“Theme for The Irishman� – Robbie Robertson
“Song of the Barefoot Contessa� – Hugo Winterhalter & His Orchestra
“A White Sport Coat (and a Pink Carnation)� – Marty Robbins with Ray Conniff
“Canadian Sunset (Single Version)� – Eddie Heywood
“Honky Tonk, Pt. 1� – Bill Doggett
“Melancholy Serenade� – Jackie Gleason
“Qué Rico el Mambo� – Pérez Prado
“Cry� – Johnnie Ray & The Four Lads
“Sleep Walk� – Santo & Johnny
“The Time Is Now� – The Golddiggers
“Al Di La� – Jerry Vale & The Latin Casino All Stars
“Pretend You Don’t See Her� – The Latin Casino All Stars.

Glenn Miller Chattanooga Choo Choo

https://www.youtube.com/watch?v=bGBwmLRNLJ4

" Oh What A Night " The Dells.

So many to choose from.
https://www.jazzstandards.com/compositions

Mexicalli Rose, South of the Border, and other Gene Autry songs. I played these songs to death as a toddler back in the 50's on my grandmother's victrola.

It may actually be from 1961, but my favorite song is "A Thousand Stars" by Kathy Young and The Innocents.

How did I pick just one? As others have said, there are many. I just mentally went through all my favorite songs and found the one that I had heard and liked the earliest.

Close.

http://www.oldiesloon.com/ca/kfwb601022.htm

Agreed, but I'd add a fun little tune Beep Beep.

"Since Ma's Gone Crazy over Crossword Puzzles" This came out in the 1920's during the crossword puzzle craze. i
I have two identical Apex (Canadian) 78's.
Lots of good kazoo playing. I don't think it shows up on the web anywhere.

Two of my favourites are :

In the heat of the night (Ray Charles)

https://www.youtube.com/watch?v=Va1cNEBu7ZE

Stardust (Nat King Cole)

https://www.youtube.com/watch?v=DjU6ZjrQulc

There are others, but among the older songs, these two I can listen to often.

A great tune by Ray Charles, John, but 7 years past the cutoff.

How about "I Got a Woman" way uptown, that's good to me, oh yeah. 1954.
https://www.youtube.com/watch?v=7XgrpxRjHuM

Back then, I liked the Disney tunes like "Davy Crockett" and "Jim Bowie" and any tune by Johnny Horton or Roger Miller. A later favorite was Mitchum's "Thunder Road". Who didn't like that tune?

Ray Charles struck a chord with "I can't Stop Lovin You" and "You Don't Know Me". But that was 1962.

Ciose enuff.

My two favorites by Ray were the instrumental, "Rockhouse", 1958, and the R&R "What'd I Say", 1959.

Oh, HECK yes!

You're no doubt speaking of the mid-50's original. I grew up on the 1969 remake.