Me and My Shadow

About

Originally written in 1927 by Al Jolson, Billy Rose and Dave Dreyer, Me and My Shadow became a vaudeville favourite and was later reimagined as a Rat Pack anthem by Frank Sinatra and Sammy Davis Jr. in 1962. Robbie Williams’ version, recorded with his best friend and then-flatmate Jonathan Wilkes, pays affectionate tribute to that partnership while turning it into something unmistakably personal. Their playful chemistry transforms the standard into a celebration of loyalty and friendship.

Recorded live in the studio, the ad-libs were spontaneous, the laughter genuine. Williams and Wilkes trade jokes and harmonies over Sidwell’s brassy arrangement, updating Sinatra’s lyric “We’re closer than Bobby is to JFK” to the cheeky “We’re closer than Ricky to confessing he’s gay.” It’s a moment that captures the irreverence at the heart of the album — reverent toward tradition, but never afraid to wink at it.

The ad-libs were live, the laughter was real. It’s just me and my mate having fun — that’s what it should be about.Robbie Williams

At the Royal Albert Hall, the pair re-created the duet with effortless showmanship, finishing each other’s lines and breaking into laughter mid-song. Their camaraderie mirrored the original’s spirit, reminding audiences that swing, at its best, is about connection as much as craft. Me and My Shadow remains one of the most joyful and human moments on Swing When You’re Winning, a toast to friendship wrapped in swing’s finest tailoring.