A fan of David Crosby since his days with the Byrds, Phil Collins asked the CSN legend to sing on his fourth solo album, …But Seriously, during their first meeting.

“He will pick out notes from the air that nobody else would sing,” said Collins of Crosby. Collins had previously crossed paths with Graham Nash and Stephen Stills but never met Crosby until an Atlantic Records 40th anniversary party during the late ’80s.

“I said, ‘I’ve got to meet David,” added Collins. “He’s a big hero of mine. So they introduced me to him, and I went backstage and [I] said ‘Can you sing on my next album?’ He said ‘Sure.’”

Years later, Collins and Crosby’s friendship developed into something deeper than lyrics. In 1994, shortly after being diagnosed with Hepatitis C, Crosby underwent a liver transplant surgery, which Collins paid for. “Phil Collins did help me enormously,” said Crosby in 2014. “I’m not going to get into the specifics about how; it’s nobody else’s business but mine and Phil’s.”

By the late ’80s, Crosby and Collins had already started a nearly decade-long collaborative run. Here’s a look at four of their musical collaborations from 1989 through 1998.

[RELATED: The ’90s Hit Phil Collins Originally Wrote for Daughter Actress Lily Collins]

“Another Day in Paradise” (1989)

Collins’ fourth album, …But Seriously, was a departure from his previous, pop-loaded No Jacket Required. Its lead single, “Another Day in Paradise,” addressed the issue of homelessness, how it is often overlooked, and was one of two tracks featuring Crosby on backing vocals.

“I sent him a tape of the two songs, and he loved them, came in, and he was wonderful,” recalled Collins. “We sat down at the piano … he showed me his ideas, and he did exactly what I thought he’d do. He came up with these ideas that nobody else would think.”

When released on October 23, 1989, “Another Day in Paradise” topped the Billboard Hot 100, marking Collins’ seventh and final No. 1, and won the Grammy for Record of the Year in 1991. Crosby also joined Collins for the live performance of “Another Day in Paradise” at the 1991 Grammy Awards.

She calls out to the man on the street
“Sir, can you help me?
It’s cold and I’ve nowhere to sleep
Is there somewhere you can tell me?”
He walks on, doesn’t look back
He pretends he can’t hear her
Starts to whistle as he crosses the street
Seems embarrassed to be there

Oh, think twice
‘Cause it’s another day
For you and me in paradise
Oh, think twice
‘Cause it’s another day for you
You and me in paradise

“That’s Just the Way It Is“(1990)

The second song Crosby lent his vocals to on …But Seriously was Collins’ anti-war ballad, “That’s Just the Way It Is,” addressing the conflicts in Northern Ireland.

“Ireland of course, it’s on the doorstep [of England] but everywhere else in the world it’s just another news report,” said Collins, “but if you are living in England and you just sort of constantly [hear of] people getting blown to smithereens because this thing that’s been going on … You see newsreels of kids throwing petrol bombs because their brothers throw them and then their dads throw them and their dad’s dad and it’s just bred, inbred, now this violence and I just thought someone somewhere, and it’s got to be from both sides, has got to say ‘Hang on, life means more than this. This has got to stop.’”

Released as a single in 1990, “That’s Just the Way It Is” peaked at No. 26 in the UK and features Collins and Crosby harmonzing on the pre-chorus: And I don’t know why, why do we keep holding on / I don’t know why, pretending to be, oh, so strong / Oh, why, is there something I don’t know? / Or something very wrong, with you and me, or maybe

All day long, he was fighting for you
And he didn’t even know your name
Young men come and young men go
But life goes on just the same

And I don’t know why, why do we keep holding on
I don’t know why, pretending to be, oh, so strong
Oh, why, is there something I don’t know?
Or something very wrong, with you and me, or maybe

That’s the way it is
That’s the way it is

“Hero,” David Crosby, featuring Phil Collins (1993)

A year before David Crosby underwent liver transplant surgery, he released his third solo album, Thousand Roads, which was his last album for 21 years before releasing Croz 21, and his final, For Free, before he died in 2023. Thousand Roads features songs written or co-penned by Joni Mitchell (“Yvette in English”), John Hiatt (“Through Your Hands”), and opens on “Hero,” a song Crosby co-wrote with Collins.

Produced by Collins, who also played drums, keyboards, and drum machine on the track, the song covers the complexities of life and the good versus evil within human nature.

It was one of those great stories
That you can’t put down at night
The hero knew what he had to do
And he wasn’t afraid to fight

The villain goes to jail
While the hero goes free
I wish it were that simple for me

And the reason that she loved him
Was the reason I loved him, too
And he never wondered
What was right or wrong
He just knew, he just knew

In 1993, Collins also released a demo version of “Hero” with his vocals only as a B-side to “We Wait and We Wonder” from his fifth album, Both Sides.

“Hero,” CPR, featuring Graham Nash and Phil Collins (1998)

Five years after releasing Thousand Roads, Crosby delivered a live album with his jazz trio, CPR, alongside guitarist Jeff Pevar, and Crosby’s son, keyboardist James Raymond. Recorded at the Wiltern Theater in Los Angeles in November 1998, Live at the Wiltern features Crosby’s CSN bandmate Graham Nash is also a special guest, joining him and Collins on a live version of “Hero.”

Photo: David Crosby (l) and Phil Collins during AFI Tribute to Steven Spielberg at Beverly Hilton Hotel in Beverly Hills, CA. (Jeff Kravitz/FilmMagic, Inc)