Why was Paul McCartney so “terrified” to work with Barbra Streisand?

When it was released on his 2012 album Kisses on the Bottom, the track ‘My Valentine’ immediately stood out as one of the better original Paul McCartney compositions of the past few decades.

Since most of the selections from that terribly titled album were covers of time-tested jazz and pop standards, Macca put himself into that same sort of mindset with his own writing, trying to tap into the vein of an Irving Berlin or Johnny Mercer rather than worrying about what was going on in the 2010s.

It didn’t hurt that he could also invite just about anyone he wanted to take part in the recording of ‘My Valentine’, meaning that the already solid song was given considerable extra oomph by the presence of Eric Clapton and John Pizzarelli on guitar, Diana Krall on piano, and the London Symphony Orchestra handling the heavy lifting.

‘My Valentine’ was a minor hit upon its release, and enjoyed a second life when Michael Bublé gave it the full Bublé treatment a decade later on his 2022 album Higher, with McCartney assisting on production. Those first two go-rounds with the song, however, despite the high-profile collaborators involved, didn’t hold a candle to the high stakes McCartney felt when he returned to ‘My Valentine’ yet again in 2025, this time in the form of a duet with the one and only Barbra Streisand.

“Nerve-wracking. Nail-biting!” McCartney said of the experience of recording with Babs, as recounted to Paul McCartney, “I did the session with her in LA, and I was pretty terrified. I think the session was about three hours, you know, a normal kind of session, and it was produced by my friend Peter Asher. But it started off with a big 40-piece orchestra on the Sony lot, which is one of the old Hollywood film studios; it’s very impressive. And we were on ‘The Barbra Streisand Scoring Stage’, so no pressure there!”

Interestingly, Streisand and McCartney were born less than two months apart in 1942, and both came up in working-class families in Brooklyn and Liverpool, respectively. Streisand’s debut album also came out in 1963, same year as The Beatles’ first record. For the past 60 years, they have remained two of the most famous, if not the most famous, singers on the planet, making Babs one of the few figures one could easily imagine McCartney being slightly intimidated by.

“I thought, ‘Well, this will be easy because it’s my song,” Paul said of the ‘My Valentine’ session, “What can go wrong?’ But what I’d forgotten was that they’d arranged it so that it had to go in Barbra’s key and then in my key. So, to get from Barbra’s key into mine was kind of difficult, and I had to launch in not knowing what key I was in. Mine was lower, hers was higher. It wasn’t easy at all!”

Fortunately, to the surprise of no one, everything worked itself out, as the new version of the tune made its debut on Streisand’s latest album, The Secret of Life: Partners, Volume Two.

McCartney gushed about working with Streisand, saying that she was great and that he was taken aback by the holistic nature of her creativity, adding, “They were filming the session, and as soon as we went in, she said, ‘Who put that camera there? That shouldn’t be there; bring it over here. And what about those lights?’ I thought, ‘Wow, you’re directing it!’ But then I suddenly remembered she’s directed three big movies. She’s a smart cookie.”

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