He lent fine and very Gilmour-guitar solos to tracks from two Eighties McCartney albums, 1984's Give My Regards to Broad Street and 1989's Flowers in the Dirt. David played guitar on The Wings’ single ‘Rockestra Theme’ and 1999’s Run Devil Run.
Also in 1999 McCartney, Gilmour and Paice along with Mick Green and Pete Wingfield appeared on the BBC talk show.
Gilmour and his Pink Floyd bandmates had the angst-ridden plasticity of their adolescent years soundtracked by The Beatles. “I really wish I had been in the Beatles,” Gilmour told Mojo in 2016. “[They] taught me how to play guitar; I learnt everything. The bass parts, the lead, the rhythm, everything. They were fantastic.
Pink Floyd would acquaint with The Beatles, having first met in 1967 at Abbey Road Studios.
“I’m a kid, really,” Gilmour says, “You get into Studio Two at Abbey Road, you’re sitting there with Paul McCartney, and your guitar is plugged in. You think that’s an ordinary day’s work, but of course, it isn’t; it’s magical! Managing to persuade him to sing ‘I Saw Her Standing There’ at the Cavern, with me doing the John Lennon parts, was absolutely fantastic.”“I’ve been in The Who, I’ve been in The Beatles, and I’ve been in Pink Floyd,” Gilmour jested. “Top that, motherfucker!” (Farout)
In his 2021 book The Lyrics: 1956 to the Present, McCartney discussed his decision to enlist Gilmour’s guitar talents for Give My Regard To Broadstreet. The former Beatle labelled the Pink Floyd guitarist as “a genius”. Detailing further, he added: “David Gilmour plays the solo on the record. I’ve known him since the early days of Pink Floyd. Dave is a genius of sorts, so I was pulling out all the stops. I admired his playing so much, I’d seen him around; I think he’d just done his solo About Face album. So I rang him up and said, ‘Would you play on this?’ It sounded like his kind of thing.”
Watch the full concert of Paul McCartney and David Gilmour at Cavern Club, 14 December '99
It was McCartney's first appearance at the Cavern since The Beatles' final show there on 3 August 1963.
I am going back for just one night as a nod to the music that has always and will ever thrill me. I can't think of a better way to rock out the end of the century than with a rock 'n' roll party at the Cavern. (PaulMcCartney)
The group performed “All Shook Up” and “Honey Hush” and while Gilmour and McCartney performed “Your Loving Flame” as and Sir Paul tackled “The Long And Winding Road” solo.
At the end of the Nineties, Gilmour took on guitar duties when the former Beatle recorded Run Devil Run, a studio album of mostly Fifties covers with a few original tunes thrown in.
Paul had some reservations as he thought the Cavern was on the wrong side of the road. He was told that it was 50% on the same site and had the same address, albeit it is eight foot deeper than the original Cavern. The plans of the back stage were within 12 feet of where they used to play, so it was more relevant to play the back stage than the front. There was also talk of Paul playing a theatre in London. Geoff knew that if he put Paul together with the Cavern, it would be an explosive news story. Stick him in Gambier Terrace; it's a cute angle. Stick him in a theatre in London; it's just another gig. They only agreed to the Cavern three weeks before it happened. We were told not to tell anybody and Paul would announce it on Parkinson. (Bill Heckle, Cavern Club owner
The Cavern, Spencer Leigh)
McCartney and his band rehearsed in the afternoon of 14 December in front of a few lucky onlookers, including Bill Heckle and Apple's Neil Aspinall. A leather sofa was removed from the Cavern's dressing room in case it offended McCartney, a strict vegetarian and animal-rights campaigner.
McCartney was also reunited with Bob Wooler, the Cavern's legendary MC who had introduced The Beatles countless times. (Beatles Bible)
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