There’s something thrilling about hearing a singer (whom you previously presumed wouldn’t have touched jazz with a 10-foot pole) lock down a swing standard. Here are four of our fave artists who made the soft shoe leap.

Album cover artwork for Robbie WilliamsRobbie Williams

A little over 10 years ago, former Take That star Robbie Williams decided to throw us a tuxedo curveball and release the phenomenally successful Swing When You’re Winning (2001). The title is a very clever wordplay on his previous album, 2000’s Sing When You’re Winning, which spawned the mega-hits Rock DJ, Better Man, and Kids (with Kylie Minogue).

On its swingin’ counterpart, Robbie proved his caramel croon could easily tackle classics like Mack the Knife, Beyond the Sea (both previously hits for Bobby Darin in 1959), and Nat King Cole’s legendarily rollicking Straighten Up and Fly Right. Robbie also graciously received some leg-up cred via duets with Nicole Kidman (on Somethin’ Stupid; at the time, Kidman was riding high on accolades for her singing performance in Baz Luhrmann’s film Moulin Rouge!, out the same year) and ol’ Blue Eyes himself, Frank Sinatra, on It Was a Very Good Year.

It was a terrifically successful venture for Williams, and he returned to swing covers for his tenth album, Swings Both Ways (2013).

Album cover artwork for Tony Bennett and Lady Gaga with black vinyl record popping outLady Gaga

Let’s face it: Ms Pokerface has always been versatile. But when the pop maven released Cheek to Cheek with jazz legend Tony Bennett in 2014 – just a year after her EDM and synth-techno jam Artpop – critics were a little stunned. Also, who was this curly-mopped brunette clasping hands with Tony Baloney on the album cover?!

Needless to say, Lady Gaga utterly nailed it. She’d already recorded with Bennett before, of course – a rendition of The Lady is a Tramp for Bennett’s 2011 Duets II album – but this time she turned it up to 11. Accompanied by a live band, Gaga and Bennett laid down classics with a modern twist, like Cole Porter’s Anything Goes, Duke Ellington’s It Don’t Mean a Thing (If it Ain’t Got That Swing), and the title track, an instant hit when it was performed by Fred Astaire in his 1935 comedy with Ginger Rogers, Top Hat.

The results were so stunning, Gaga and Bennett followed it up with last year’s Love For Sale, which received six Grammy noms and bagged Bennett a Guinness World Record for being the oldest ever person to release an album of new material (95 years and 60 days).

Read our album review of Lady Gaga and Tony Bennett’s Love For Sale.

Album cover artwork for Rod StewartRod Stewart

Rod the Mod had released a massive 19 solo albums before his official foray into jazz, which arrived in the form of It Had to Be You. If anyone was sceptical that the raspy, bouncy-haired pop-rocker couldn’t make it stick, they’d have had to eat their hat; It Had to Be You was just the first in what would become a five album string: The Great American Songbook series.

In addition to its title track, Rod got his paws on classics like The Way You Look Tonight (made famous by Fred Astaire’s performance in his 1936 film Swing Time), Cole Porter’s Ev’ry Time We Say Goodbye, and That’s All, recorded by Nat King Cole in 1953 and Bobby Darin in 1959.

Stewart assembled a fabulous supporting band to record the LP, which included pianist and Grammy-nominated film composer Randy Kerber (Forrest Gump, The Color Purple, Titanic), guitarist and producer Jimmy Rip (Debbie Harry, Mick Jagger), and Grammy-winning pianist and conductor Randy Waldman (Frank Sinatra, Michael Jackson, Whitney Houston, Beyoncé).

Debbie Harry

New Wave and disco-pop pioneer Debbie Harry took a hot sec away from her highly successful band Blondie in 1994, to contribute guest vocals to an album from avant-garde New York City band The Jazz Passengers. Titled In Love, the record also featured vocals from Jeff Buckley and Mavis Staples.

Harry loved the experience so much that she decided to put her back into it, and two years later the world was gifted Individually Twisted, the 1996 collab album between the vocalist and the jazz ensemble. With Harry’s playful cabaret timbre, the album’s funky grooves featured sax (by Roy Nathanson, co-founder of the group and famous for playing two saxophones at once), trombone (from Curtis Fowlkes, co-founder of the band who has played with Lou Reed, Harry Shearer and Sheryl Crow), and guitar (by Marc Ribot, who’s worked with Tom Waits and Beck) as the backdrop to originals and some gorgeous standards.

There’s even a duet with Elvis Costello, Doncha Go ‘Way Mad (previously recorded by Frank Sinatra and Ella Fitzgerald). Harry still occasionally appears with The Jazz Passengers, most recently grabbing the mic for the band’s 2019 JPMP Gala fundraiser performance.