This is one of two original tracks from Paul McCartney's 2012 "pop standards" album, Kisses On The Bottom, the former Beatle's tribute to classic songwriters of the 20th century. Said Macca: "When I kind of got into songwriting, I realized how well structured these songs were and I think I took a lot of my lessons from them. I always thought artists like Fred Astaire were very cool. Writers like Harold Arlen, Cole Porter, all of those guys – I just thought the songs were magical. As I got to be a songwriter I thought it's beautiful, the way they made those songs."
The album marks the first time McCartney recorded without playing guitar, bass or piano. Instead he was backed by Jazz singer Diana Krall's band. "It was very spontaneous, kind of organic, which then reminded me of the way we'd work with the Beatles," explained McCartney. "We'd bring a song in, kick it around, and by the time everyone kind of had an idea of what they were doing, we did the take live in the studio."
This ballad features some guitar work from Eric Clapton. Probably the best known track that features the talents of both McCartney and Clapton is the Beatles' classic "
While My Guitar Gently Weeps."
The "Kisses On The Bottom" title is taken from a lyric on the album's opening track, a cover of Fats Waller's 1935 hit "I'm Gonna Sit Right Down And Write Myself A Letter." The lyric is: "I'm gonna sit right down and write myself a letter and make believe it came from you/I'm gonna write words oh so sweet/A lot of kisses on the bottom/I'll be glad I got 'em."
McCartney admitted to London's Sunday Times that his love of "mischief" led him to pick the controversial title. "I like mischief," he said. "It's good for the soul, it's always a good idea — if only because people think it's a bad idea." McCartney added that his record label was concerned when they learnt of his intentions for the title of the disc. "I made the suggestion and got this nervous text from the label which said, 'Paul, under no circumstances can we do this,'" he said. "One of the guys said he felt like he'd been punched in the gut."
Paul penned this song whilst sheltering from the rain during a holiday in Morocco with his wife Nancy Shevell. He revealed to Mojo magazine: "It was inspired by the hotel pianist, an Irish guy who liked to drink. He would rattle through this repertoire of old songs from my dad's era and before. It was inspiring - his command of them, and his love for them! I had a moment one afternoon when the hotel was quiet and I just got on the piano. The spirit of what he was doing led me down the path."
McCartney directed the song's black-and-white music video, which features Hollywood stars Natalie Portman and Johnny Depp each interpreting the lyrics of the song using their own form of sign language. Depp plays guitar in his version and recorded the track's guitar solo live, which was performed on the record by Eric Clapton. McCartney worked with cinematographer Wally Pfister (Inception, The Dark Knight), editor Paul Martinez and producer Susanne Preissler to create the clip, which was based on an original idea by Stella McCartney. Asked why he picked Portman and Depp to star in the video, Sir Paul said: "Well, they're just nice people, some friends from way back and they were just very kind to do it. I was very pleased to work with them."
Deaf music fans noted that both actors made unfortunate slip-ups with their translations. Depp embarrassingly makes the gesture for the word "enemy" while attempting "valentine" and both he and Portman make the motion for the word "tampon" instead of the word "appear."
Kisses On The Bottom won the 2013 Grammy for Best Traditional Pop Vocal Album. It was Sir Paul's 17th Grammy award and his first for a record containing new material since his Beatles days.
The Canadian crooner Michael Bublé
reworked "My Valentine" for his 2022 album
Higher. "His manager sent my manager a note from Paul saying, 'We hear you're doing this record, we think you'll do a great job covering this song. It's a song that means a lot to him,'" Bublé said.
Bublé was honored to be asked to cover the song. "I wanted to make it my own, but also pay respect to the original," he said. "I think I did a good job."
Paul McCartney produced Michael Bublé's version himself.
During an interview with Variety, McCartney reminisced about how Bublé had invited him to attend a session in New York to help with producing it. The former Beatle saw Bublé work with a large orchestra and perform the vocals, and Paul provided minor suggestions, including specific ways to sing certain phrases. McCartney joked that he was taken aback when Michael Bublé didn't kick him out of the studio. Instead, Bublé welcomed his input, and their collaboration turned out to be "magic," as the Canadian singer never considered removing McCartney from the session.
"He is who you wish he would be," said Bublé. "He saunters into the studio alone. No group. No security. And he looked like he came in on a skateboard because he kind of floats when he walks. He wanted to be just a humble servant to the music."
Barbra Streisand recruited Paul McCartney for
a duet version of "My Valentine". Their rendition is included on Streisand's 2025 star-studded
The Secret of Life: Partners, Volume Two album, a sequel to her 2014 LP
Partners.
Unlike many modern collaborations that are pieced together remotely, Streisand and McCartney recorded "My Valentine" together in the studio.
