How Sting and Robert Downey Jr struck up an unlikely lifelong friendship

16 October 2024, 15:40

The world of Hollywood is full of unlikely friendships.

But there are two stars whose 'bromance' seems more unusual than most, who are from two sides of the entertainment world: Sting and Robert Downey Jr.

Strangely enough, the pair of pals don't just hang out behind the scenes either - they've performed on stage together too.

• Sting's 10 greatest songs ever, ranked
• When Sting’s son Joe joined him for sensational duet of ‘Every Breath You Take’
• How Sting and Trudie Styler's infamous tantric love sessions influenced one of his songs
• Sting’s secret to his long and loving marriage to Trudie Styler: A relationship timeline

The Police's former frontman has invited the Iron Man icon to sing alongside him on several occasions over the course of their thirty year-plus friendship.

So how did Sting and Robert Downey Jr become buddies? Here's everything you need to know:

When did Sting and Robert Downey Jr first meet?

During a 2016 interview with Howard Stern on SiriusXM, Robert Downey Jr revealed his first interaction with Sting was a slightly awkward one:

"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 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.

"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 recognised me from [1987 film] 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."

Downey Jr was brimming with self-confidence at that time in his life (evidently) and truly believed that if Sting heard him sing, "he would understand that I’d be opening for him in two weeks once we finished the demos".

Reflecting on his outlandish move, he joked in 2016: "I mean, look, a couple of them had promise but have you heard of them? No, those songs never made it."

So, can Robert Downey Jr actually sing?

In fairness, Robert Downey Jr can actually sing, and has featured on the soundtracks to several of his films.

He sang in 1992 biopic Chaplin, having played the titular Charlie Chaplin which bagged him a BAFTA Award for Best Actor as well as an Oscar nomination.

Downey Jr also sang in The Singing Detective in 2003 and Kiss Kiss Bang Bang in 2004, before releasing his debut solo album The Futurist that same year.

His most commercially successful recording however is a cover of Joni Mitchell's 'River' from the Christmas episode of law comedy-drama Ally McBeal which featured in 2000's Ally McBeal: A Very Ally Christmas.

It was his brief stint starring on the show which would reunite him with his music idol that he tried to convince of his own musical talents years earlier.

When did Sting first sing alongside Robert Downey Jr?

Robert Downey Jr. and Sting- Every Breath You Take

After a series of well-publicised personal issues throughout the nineties, Robert Downey Jr's acting career had stalled despite his early promise. That was until he joined the cast of Ally McBeal.

He played the main character Larry Paul throughout series four and featured as a guest throughout series five.

But there was one particular episode that stands out to fans of the actor - and of Sting's, too.

In the 'Cloudy Skies, Chance Of Parade' episode of the series, Sting cameos after he's being sued, and employs Larry as his lawyer.

Larry, who misses Ally McBeal's birthday after having had to represent Sting, needs to pull out all of the stops so convinces the music icon to duet 'Every Breath You Take' with him.

Though it was a fictional coming together for Sting and Downey Jr, it showcased the latter's talent, and sparked a great friendship between the two.

Did Sting ever duet with Robert Downey Jr again?

Robert Downey Jr. & Sting - Driven To Tears - Live @ The Beacon Theater

Robert Downey Jr's self-confidence when it came to his own musical abilities was fairly justified - at least in the eyes of Sting, who knew their duet on Ally McBeal wasn't merely a fluke.

He impressed the 'Fields Of Gold' legend with his husky tones so much in fact, that Sting invited him on stage for several more duets.

The pair of pals reenacted their sumptuous duet in 2001 at a Gala benefit concert, and again that same year in aid of the Hollywood Sunset Free Clinic alongside Elton John.

Downey Jr stole the show however when Sting invited the Oppenheimer star to sing alongside him once again in 2011, at a fundraiser for the singer's 60th birthday held at the Beacon Theatre in New York City.

They came together to perform 'Driven To Tears' from The Police's 1980 album Zenyatta Mondatta, and Robert more than held his own.

Is there a chance we'll see Sting and Robert Downey Jr collaborative album in the future?

After twenty-five years of friendship, Sting and his wife Trudie Styler brought up the demos Robert recorded and brazenly handed to them upon their first meeting, a memory he thought might not have resurfaced.

"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 in the 2016 interview on SiriusXM.

"And I said, 'Gimme that tape back!' If they played it, they rewound it, put it back in the box and re-taped it."

Opening up about getting the chance to perform with his dear friend again, Robert remembered that it wasn't all plain sailing.

"Not a rehearsal, he ran me ragged," Downey continued. "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.

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

Whilst Downey fondly dubbed the duets as both thrilling and exciting, he doubts they'll ever get in the studio together despite Sting's praise, which he took with a pinch of salt.

"At the same time, he’s largely responsible for that performance going well. 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'."

An album of duets featuring both Sting and Robert Downey Jr is perhaps unlikely at present, but is maybe as unlikely as the pair's lifelong friendship.