Even years later, Robert Downey Jr.’s performance at Sting’s 60th birthday celebration still leaves music fans speechless. “Wait—Iron Man can sing like that?!” has become a common reaction online. Despite the widespread amazement, Downey remains humble when talking about his long friendship with Sting—a relationship that traces back decades before that memorable duet.
Downey recalls meeting Sting in his mid-twenties, back when he fancied himself a budding songwriter. After one of Sting’s concerts, the young actor nervously tried to hand the rock legend a demo tape in a stairwell. Sting was caught off guard—but his wife, producer Trudie Styler, immediately recognized the actor from Less Than Zero and greeted him warmly. The tape disappeared into history until, 25 years later, Sting and Trudie rediscovered it. When they asked Downey if he wanted it back, he jokingly told them, “If you listened to it, please rewind it and tape it shut again.”
That funny memory didn’t stop Sting from inviting Downey to perform at his 60th birthday charity concert in 2011 at New York’s Beacon Theatre. The pair took the stage for a mesmerizing rendition of “Driven to Tears,” originally from The Police’s 1980 album Zenyatta Mondatta.
When Downey began to sing, the audience couldn’t believe their ears. His smooth, soulful tone drew comparisons to Nils Lofgren and Robert Palmer. Commenters on the video were floored: “A true artist! Who knew Tony Stark could pull off a Sting song?” wrote one fan. Another confessed, “I’ve heard this song dozens of times, but Downey just gave it new life.”
Even radio host Howard Stern admitted he was blown away, telling Downey during a 2016 interview that his version of “Driven to Tears” was so good it made Sting’s original sound almost secondary. Downey, ever gracious, wouldn’t hear of it—he praised Sting as a “practically perfect” mentor who pushed him to deliver his best.
But this wasn’t the first time the two icons shared a stage. Their first duet came in 2001 on the TV series Ally McBeal. In the episode “Cloudy Skies, Chance of Parade,” Sting—playing himself—teams up with Downey’s character, Larry Paul, for a heartwarming performance of “Every Breath You Take.”
Of course, Downey’s musical flair didn’t stop there. He’s lent his voice to films like Chaplin (1992), The Singing Detective (2003), and Kiss Kiss Bang Bang (2005). In 2004, he released his own album, The Futurist, featuring eight original tracks that earned critical praise, though he later admitted that the recording process took too much time away from his family.
And let’s not forget his most commercially successful recording—his moving rendition of Joni Mitchell’s “The River” on the Ally McBeal: A Very Ally Christmas album in 2000, which still melts hearts every holiday season.
