5 Songs That Make Me Wish I Were a Man

One of the things I love about singing jazz is that very rarely is anything off limits – whether you be white or black, old or young, male or female (or anywhere in between) the Great American Songbook (and beyond) is yours for the taking. If you have something to add to the conversation of the music, the music is there for you – and nothing’s so precious that a pronoun here or there can’t be changed. Singers and instrumentalists take what inspires them regardless of gender preference and make it their own.

That said, there are a few but notable songs that I know can never be mine, due to my irrefutable gender (or not without a very flagrant drag performance). These next songs are ones I adore – and the only way I can share them is in this post. So hat’s off to the boys and the songs written for them!.

#5 Satin Doll (Composed by Duke Ellington & Billy Strayhorn; Lyrics: Johnny Mercer)

This one, alright, I’ve done it. It’s not inconceivable that I could pick up a doll at some joint, or be impressed that she speaks Latin…but there’s something about the swagger of the lyric, and the rhyme of “amigo” – it’s self-referential and you can’t replace it. Great female vocalists have changed the perspective to make it work, but for me the necessary substitutions and perspective shifts lose the cool ease of the original. Point, dudes.

Here’s Dr. John giving it a little twist:

#4 Best Man (Jason Harrow, Andrew Joel Thompson & Carlton Errington Grant)


What a charmer of a song, sung by the charming Nat King Cole. And it’s a great punch line – you have to agree, it just wouldn’t be the same as “maid of honor”.

#3 It Was Very Good Year (Irvin Drake)

The nostalgia, the yearning, the pride of remembered virility. It’s one of the greats, but no song for a lady (in the best possible way).

It has to be Sinatra:

#2 Soliloquy (Composed by Richard Rodgers; Lyrics: Oscar Hammerstein II)

I’m taking us out of jazz standard territory here, but this is just one of the most epic, beautiful pieces – a monologue and aria in several movements, really, sung by a man soon to be a father. There are very few pieces in musical theater, opera, or any songbook I can think of that truly inhabit the pride and terror of incipient fatherhood. This one’s for the (dramatic) boys.

Thomas Hampson has the bravado and the depth of sound to do it more than justice:

#1 A Man Ain’t Supposed to Cry (Norman Gimbel, Frankie Laine & Irving Reid)

The song is perfect and this arrangement, sublime. It’s a tune about trying to seem strong when feelings are stronger. It’s universal, as all good songs are, but so true to a man’s experience that it’s off limits to the fairer sex. To sing this lyric will be my hope for another lifetime:

Woman’s right to tears will be hers until she’ll die

But a man ain’t supposed to cry.

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