Interview

Jazz Views, 20 November 2025

Musician’s Playlist

Ian picks some of his favourite songs by Stephen Sondheim

With his new album Stephensong due for release on Friday 28th November, and the launch the evening before on 27th November at Kings Place, London, vocalist Ian Shaw explores the music of the great Stephen Sondheim.

Shaw set out to select not just classic songs but also lesser-known treasures with a view to bring a storyteller’s gift to these wonderful songs.

In a slight twist to our usual Musician’s Playlist, we asked Ian pick some of his favourite songs by Stephen Sondheim, and specific versions that have a special place in his affections.


The songs of one of the greatest lyricists/composers of all time, Stephen Sondheim, have always moved and intrigued me in equal dosage. How to choose an albums’ worth as a (mostly) jazz singer, was as daunting as it was thrilling. Those extraordinary melodies that serve the propulsion – sometimes crazed and clattering, painterly and precise, sometimes simple, hymnal and ballads – need no jazzy re-fits. Just sing what he wrote was my mantra when pianist, Barry Green and I went into the studio to record Stephensong.

Curiously, some exhilarating ‘re-fits’ have been recorded over the decades. And boy are they good, even as Sondheim ‘experts’ may scoff at some, the often divisive nature of a writer’s legacy I find amusing and a spirited challenge. Here are ten which may divide the Steveites, much the way his actual output did exactly this!

Send In The Clowns (from A Little Night Music) — Sarah Vaughan (Source: Sassy at Ronnies’ 1977)

The Rolls Royce of jazz singers, Sarah Vaughan, squeezes every drop of sadness and regret -the opposite of Glynis Johns, Judi Dench or Haydn Gwynne -whose takes on this, the most successful of Sondheim’s compositions – were narrative-driven and contextual, over Sassy’s urge to show off her entire toolbox. Fascinating that her obvious re-moulding of the simple, un-rangy tune, remained solidly the same at every concert.

The Ballad of Sweeney Todd (from Sweeney Todd) — Lea de Laria

This is a brilliant, swinging arrangement of this dark lyric. I worked with Lea (and guested on her ‘Live at Smoke’ album in New York) and loved how she took songs from all sources (college rock, Bowie, Sondheim). This, from her ‘Double Standards’ record, really works.

Everyday A Little Death (from A Little Night Music) — Grover Washington, Geoff Keezer, Christian McBride, Marvin ‘Smitty’ Smith.

In this song, Charlotte sings of the horrors of relationships. A really strong, simple tune, clearly not sung here, so already the purists are fizzing. But the combination of these ace players, making a fabulous contemporary fist of a Sondheim melody, is exciting.

Somewhere (from West Side Story) — Aretha Franklin (from Hey Now Hey)

Produced by Quincy, and driven from the piano by Aretha, this I heard when I was eleven, the first time I was aware of the song. Aretha is in church here, so the melody moves away from the score. It is beyond thrilling and Phil Woods’ alto is glorious. I recorded it note for note as written but retained the memory of this affecting session. It inspired me.