A Very Gentle Gentleman

Rufus Wainwright. Photo by Tina Tyrell.

Just when many proclaim “Last of!” or “Never again!” along comes a chap like Rufus Wainwright, the sort of entertainer some say “they just don’t make anymore.” Sir Elton John, for one, calls him “the greatest songwriter on the planet.”

The alchemy behind an artist like Wainwright is rare and strange (his parents are cult ’70s music icons Loudon Wainwright III and Kate McGarrigle). The Wainwright formula doesn’t make sense in the rulebook of modern pop: He’s a funny and decadently gay dandy. “I got the outfit for the party but you’ve taken away the invitation,” he croons on “Rashida” from the 2012 album Out of the Game. And he’s an outspoken advocate for gay marriage and a heart-on-your-sleeve troubadour. In “California,” from his 2001 almost-hit record Poses, he sings blithely: “California. You’re such a wonder that I think I’ll stay in bed.” In 2007, Wainwright recreated Judy Garland’s infamous Carnegie Hall performance with “Rufus Does Judy at Carnegie Hall.”

But at its heart, Wainwright’s work has a dark, honest, if often sardonic and theatrical, vein of real sadness rooted in sexuality and addiction. In the melancholy and orchestral “Montauk” from Out of the Game, he sings, “One day you will come to Montauk and see your dad wearing a kimono, and see your other dad pruning roses,” before bemusedly quipping, “Hope you won’t turn around and go.”

See the Grammy nominee at The Shedd, returning after a 10-year hiatus.

Rufus Wainwright plays 7:30 pm Friday, Oct. 25, at The Shedd; $31.25-$49.