Spinner

The 25 Most Exquisitely Sad Songs in the Whole World: No. 12

'In the Wee Small Hours of the Morning'
Frank Sinatra (1954)

The Breakdown: Ol' Blue Eyes parlayed his painful divorce from movie star Ava Gardner into a career makeover: the lonely guy at the end of the bar.

The Waterworks: "You'd be hers if only she would call."

Casualty Count: One Hollywood marriage, countless nights of sleep.

All Sad Songs

Listen to 'In the Wee Small Hours of the Morning'

Buy it on iTunes

All the AOL Music info you want to know

50 Cent, Street King: Rapper Visits…

The Boombox

AP Photo/World Food Programme, Rose Ogola NAIROBI, Kenya (AP) - Rapper 50 Cent…

Grammy Acceptance Speeches: Watch 30…

AOL Music Blog

FilmMagic, Getty, WireImage It's been a busy week for God. Besides helping…

Earl Sweatshirt Returns, Releases New…

The Boombox

YouTube.com Ironically, Earl Sweatshirt was one of the most visible members…

See all AOL Music »

Add a Comment

Sign in »
*0 / 3000 Character Maximum

40 Comments

Filter by:
Liz

His voice never failed even in his old age, smooth as honey.
Now get the really sad part. Ava is buried not too far from
where I live now. He used to come and visit her grave and
bring her flowers until he was too old, ill to make the trip.

Saddest song I have ever heard though is Leader of the Band by Dan Fogelberg. I'm not sure how to spell the last name, but I have seen plenty of grown men cry over that one.

February 20 2010 at 1:31 AM Report abuse rate up rate down Reply
Chiabone

This is a really good addition to the list. Frank Sinatra has a voice that can evoke a myriad of emotions. This is a song that truly sounds as though it came from a man with a fractured heart.

November 25 2007 at 1:32 AM Report abuse rate up rate down Reply
enne

im telling you "gloomy sunday" is the most depressing song ever. especially if you know the history of it...

November 23 2007 at 10:40 PM Report abuse rate up rate down Reply
Mike B .

Boy,do I feel old ! Listening to Frank croon,then reading some comments,most people just didn't get it. The greatest pop singer that ever lived was tearing his heart out for the love of his life. The clarity of his voice, the sadness, the whole package combined to make one of the most heartfelt sounds ever.

July 21 2007 at 4:30 PM Report abuse rate up rate down Reply
Amirah

In 1954, my dad and I would lay across the bed in our music room and listen to this song. My mom and dad were going thru a rough time and this was relaxation. He told me that one day I would understand why this song made him cry. My parents went their seperate ways a few years later and I always remembered this song. I play it when I miss my dad. But I also play it because it is a beautiful piece. By the way, I know why he cried now. True love can make you cry, even when you can't figure how to make it work. They loved each other so much but, it just didn't work out. Listen to Billy Paul's "I Was Married" from his "War of the Gods" LP. You'll understand too.

July 17 2007 at 1:28 AM Report abuse rate up rate down Reply
Diggem the Frog

For now I just want to agree with John Corcoran's vote for "At Seventeen" by Janis Ian. I heard her sing it live once on a radio talk show, about a decade ago, and she still sounded great then -- she was spellbinding. I wouldn't put it on my Top 25 list, but I love the song.

July 04 2007 at 4:45 AM Report abuse rate up rate down Reply
barb ryan

if only u would have played the song frank was singing in the motion picture with doris day.

June 18 2007 at 10:32 PM Report abuse rate up rate down Reply
Rolf Mclaren

it kills me... it just kills me everytime i listen to it.

June 14 2007 at 11:18 AM Report abuse rate up rate down Reply
joan

THIS IS BY FAR ONE OF UNCLE FRANK'S BEST. GOD, I MISS HIM AND HIS GREAT SINGING.!! THERE IS NO ONE WHO CAN PUT A SONG ACROSS LIKE HIM. TODAY'S MUSIC SUCKS.....

June 13 2007 at 5:40 AM Report abuse rate up rate down Reply
Cal Warren

When Does Sinatra go to the Bathroom?

Answer: In the Wee Wee Hours of the Morning

June 13 2007 at 4:18 AM Report abuse rate up rate down Reply