“The lyrics are beautiful,” Sarah shares, “but what I love about this song are the intricate harmonies that bring the listener on a journey through the profound experience of falling madly in unrequited love.”

Sarah recommends Billie Holiday’s lilting and sultry interpretation of the song, which was originally composed in 1938 by J. Fred Coots and Haven Gillespie. Holiday recorded two different versions of the song 14 years apart—the first in the same year it was composed, and the second one (embedded above) recorded for her 1952 album Billie Holiday Sings.

“In my opinion best sung by Diana Krall, this song speaks of the coming of age of a young love,” says Sarah.

A show-tune from the 1938 Rodgers and Hart musical The Boys from Syracuse, this jaunty and upbeat number about the unexpected joys of love has been covered by the likes of Bing Crosby, Ella Fitzgerald and Nat King Cole. Diana Krall’s version was recorded for her 1993 album Stepping Out.

“This tune is a very tragic self-portrait of Billie Holiday in addressing her husband's infidelity. It’s clear from the lyrics that the relationship will not last, but even sadder is how Holiday would rather hear less than face the truth.”

Co-written with composer Arthur Herzog Jr., this heartbreaking ballad is about Holiday’s first husband Jimmy Monroe, according to her 1956 autobiography Lady Sings the Blues. A tender piece worthy of only the most sensitive and passionate songstresses, it has been covered by Nina Simone, Etta James and Mariah Carey.

This wistful, gently optimistic piece “paints a picture of a romance that has ended amicably, with both sides wishing each other well,” Sarah says, “It's a bittersweet closing of a chapter in life and a blessed send-off into the future without one another.”

The song has its origins in the 1942 French song Que reste-t-il de nos amours?, which was adapted into English by lyricist Albert Askew Beach in 1957. Rachael Yamagata’s version is one of its more modern readings, recorded as part of the soundtrack for the 2005 romantic comedy Prime.

Composed by Jerome Kern and Oscar Hammerstein II, this song was made popular by Peggy Lee on her 1957 album The Man I Love. Sarah describes the tune as “illuminating a daydream of someone in love, who sees life with their partner stretched out ahead of them. The lyrics are hopeful and dreamy; imagine meeting someone you can see yourself settling down with forever! Better yet, imagine finding someone you love enough to choose an idyllic life with, over the chase for grander things. It's like saying, ‘You are enough for me,’ which is very sweet.”