Robert Downey Jr. Tells Howard Stern About the Time He Performed a Duet with Sting

Robert Downey Jr. has been a frequent guest on “The Howard Stern Show” and stopped by again on Wednesday, this time to promote his latest Marvel movie, “Captain America: Civil War.” During the wide-ranging interview, Downey Jr. dished on the time he performed with legendary English singer Sting.

In 2011, Sting put together a fundraiser at the Beacon Theatre for his 60th birthday. Among those he invited was Downey Jr., with whom he developed a close friendship after an awkward first encounter.

“When I was in my mid-20s, I decided I was one of the great songwriters of all time, and I had this trippy little cassette tape of all my demos that were just not good,” Downey Jr. said. “I went to one of Sting’s shows, and I accosted him in the stairwell, and I started trying to push my cassette tape in his hand.”

Downey Jr. continued, “He did what I do to people now — make sure that’s all that’s in their hand. I hand it to somebody who puts it in a box that you never see again, and then [his wife] Trudie was there and recognized me from ‘Less Than Zero’ or something and was like, ‘Hello, thanks for coming to the show.’ Totally handled me and made up for the fact that he kind of looked at me like, ‘Don’t hand me things,’ and walked away. Literally, it was a psychotic move.”

Unlike most budding singers who want to get their demos into the hands of anyone and everyone who could possibly launch their career, Downey Jr. said he only wanted Sting to hear his demo, “because he would understand that I’d be opening for him in two weeks once we finished the demos.”

He added, “I mean, look, a couple of them had promise, but have you heard of them? No, those songs never made it.”

As their friendship grew, Downey Jr. had never brought up the subject of his demo, but the tape resurfaced unexpectedly.

“So, about 25 years later, Trudie goes, ‘Robert, we were going through some of these old boxes and look what we found. Would you like this cassette tape back?'” he recalled. “And I said, ‘Gimme that tape back!’ If they played it, they rewound it, put it back in the box, and re-taped it.”

Sting offered Downey Jr. the opportunity to perform “Driven to Tears” at his birthday event, but not before he proved himself capable of sharing the stage with the 16-time GRAMMY winner.

“He ran me ragged,” Downey Jr. said. “He wanted to make sure I didn’t embarrass him … He treated me like he didn’t know me and I was auditioning to be a backup singer.”

Howard was so surprised at how well Downey Jr. sang and performed that he said Sting kind of ruined the song.

“You heard it here first, and this is why Robin and I are doing a duets album,” Downey Jr. joked.

“Sting, or people who know how to really perform and include other people, often let the other person shine and back them up,” Downey Jr. continued. “He is a practically perfect performer in every way.”

Downey Jr. called the experience thrilling and exciting. He said he received a call from Sting praising his performance, but he also took it with a grain of salt.

“At the same time, he’s largely responsible for that performance going well,” Downey said. “So it would be like if you walk somebody through something and then they don’t drop the ball, you’re gonna go, ‘God, you did a great job.'”