A Lost Love Is Hard: Jazz Singers Understand
From 
Valentine's Day is great for lovers, but what about those who have loved and lost? Don't they deserve a Valentine's gift, too? Absolutely. So here are five deliciously heartbreaking songs of love lost by some of the greatest jazz singers of all time. You might be lonely, but you're not alone.
A Lost Love Is Hard: Jazz Singers Understand
Some Other Time
Bill Evans/Tony Bennett
- Song: Some Other Time
- from Tony Bennett/Bill Evans Album [Bonus Tracks]
It took three great songwriters (or one great composer and two great songwriters) to come up with this beauty: Leonard Bernstein, Betty Green, and Adolph Comden. But it only took two great musicians to give it what we think is its definitive recording: Tony Bennett and Bill Evans. This song is included on the first of two collaborations between the world's finest saloon singer and the master of jazz piano. The other is called Together Again.
You Don't Know What Love Is
Dinah Washington
- Song: You Don't Know What Love Is
- from Jazz 'Round Midnight: Dinah Washington
When it comes to singing about lost love, you can believe every word you hear from Dinah Washington. In her 39 years on the planet, she was married seven (some say eight) times and, in this version of "You Don't Know What Love Is," she brings all her hard-won experience front and center. If you're just coming out of a romance that's gone bad, you might want to wait until you're feeling a little better before listening to this one. It's a crusher.
Blame It on My Youth
Jane Monheit
- Song: Blame It on My Youth
- from Come Dream with Me
We feel that "Blame It on My Youth" sounds best when sung by someone who's actually... well... young. Jane Monheit recorded this version of the song in 2001, when she was 20. Monheit has one of the most beautiful voices in jazz today, and she uses it to great advantage on this song.
Blame It on My Youth
Ella Fitzgerald
- Song: Cry Me a River
- from Quiet Now: Ella's Moods
Arthur Hamilton wrote this song specifically for Ella Fitzgerald to sing in the 1955 film Pete Kelly's Blues. The way the story goes, however, the film's producer didn't like the fact that the word "plebian" was in the song (go figure) and asked Hamilton to change it. Hamilton refused, the song was dropped, and Fitzgerald never got a chance to record "Cry Me a River" until 1961. It was worth the wait.
These Foolish Things
Billie Holiday
- Song: These Foolish Things
- from Lady in Autumn: The Best of the Verve Years
It's always nice to save the best for last. That's why we decided to end this list with The Queen of (Broken) Hearts: Billie Holiday. You want to hear what lost love sounds like? Just listen to this.