There’s something magical about the Great American Songbook. Maybe it’s the nostalgia. Maybe it’s the glamour. Or maybe it’s the thrill of hearing your favorite artist suddenly put on a tux, slow down the tempo, and croon like they’ve been living in a smoky jazz club since 1947.
Every generation eventually tries its hand at these classics. Some succeed beautifully. Some… well, let’s call them “historical curiosities.”
But the albums that work — the ones worth revisiting — are the ones where the artist doesn’t just sing the song. They find themselves inside it. These 15 albums do exactly that.
‘A Little Touch of Schmilsson in the Night’ – Harry Nilsson (1973)
Nilsson hires Sinatra’s arranger, goes full velvet-suit romantic, and somehow makes standards sound both dreamy and slyly unhinged.
‘Am I Not Your Girl?’ – Sinéad O’Connor (1992)
Sinéad at her boldest — heart, honesty, and a big band behind her. Her voice turns these classics into emotional gut punches.
‘Both Sides Now’ – Joni Mitchell (2000)
Joni transforms jazz standards into a late-night confession booth, anchored by her smoky, lived-in voice and Vince Mendoza’s lush arrangements.
‘Fallen Angels’ – Bob Dylan (2016)
Dylan bends Sinatra’s world into his own — ragged, intimate, and strangely tender. A saloon album for people who prefer dim lights and creaky barstools.
‘Fly Me to the Moon… The Great American Songbook, Vol. V’ – Rod Stewart (2010)
Stewart goes all-in on glamour and swing. It’s flashy, fun, and surprisingly charming — a reminder that rock stars sometimes make great crooners.
‘Long Wave’ – Jeff Lynne (2012)
ELO’s mastermind ditches bombast for warmth, creating a radio-dial love letter to the songs he grew up with. A cozy, analog-glow record.
‘Pop Pop’ – Rickie Lee Jones (1991)
Bare, strange, and beautiful — Jones turns standards inside out using only her elastic phrasing and a bassist who sounds like he’s levitating.
‘Sentimental Journey’ – Ringo Starr (1970)
Ringo’s mom asked for an album of standards. Ringo delivered — with George Martin turning the arrangements into whimsical little worlds.
‘Shadows in the Night’ – Bob Dylan (2015)
Dylan at his most vulnerable, singing Sinatra with the cracked beauty of a man sending postcards to his past selves.
‘Songs From the Last Century’ – George Michael (1999)
Stylish, smooth, and unexpectedly bold — Michael reinvents standards and even sneaks in a big-band ‘Roxanne’ because, well, why not?
‘Stardust’ – Willie Nelson (1978)
A landmark album. Willie bends melodies like they’re soft clay and turns the Songbook into a country-jazz masterpiece that stayed on the charts for a decade.
‘Thanks for the Memory… The Great American Songbook, Vol. IV’ – Rod Stewart (2005)
One of Stewart’s strongest entries — warm vocals, impeccable arrangements, and a surprising amount of emotional depth.
‘Triplicate’ – Bob Dylan (2017)
Three discs, three moods, and Dylan at his most reflective. It’s sprawling, delicate, and maybe his most committed dive into the Songbook.
‘Wee Small Hours’ – Frank Sinatra (1955)
The template. The standard of standards. Every late-night Songbook album owes a drink to this one.
‘What’s New’ – Linda Ronstadt (1983)
Ronstadt, backed by Nelson Riddle, goes full glamour and absolutely nails it. Her voice soars over arrangements that sparkle like vintage Hollywood.