The 25 Greatest Songs of Paul McCartney’s Illustrious Career
25. “Lady Madonna” (1968)

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Released as a single, “Lady Madonna” hearkened back to the Beatles’ straight-up pop days. This upbeat McCartney song was a concert favorite, though it tends to get lost as the Beatles sound of the time was much different. The sound was more personal and certainly darker (considering how it all started).
24. “Silly Love Longs” (1976)

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Steeped in his career with Wings, McCartney wrote the track as a response to those music critics who often chastised him for his tendency toward pop-style love songs. So, why not go as over-the-top as possible? The catchy “I love you …’ tune was a hit, and another No. 1 for McCartney as a writer. It remains one of his most popular songs from the Wings’ catalog.
23. “Paperback Writer” (1966)

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Keeping with the public’s apparent push for less McCartney love-themed material, legend has it he was asked by a relative to pen a song away from that topic while with the band. Though, it’s commonly believed that McCartney wrote the song after reading a newspaper article about a budding author. Released as a single, it went to No. 1 on the charts. “Paperback Writer” remains a staple at McCartney live shows.
22. “Blackbird” (1968)

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Part of “the White Album,” the piece was essentially a McCartney solo effort. Influenced by the Beatles’ time spent in India, “Blackbird” fits in well with the overall feel of the band’s self-titled album. The bird calls in the background are a nice touch, but it’s still a song that’s not necessarily for everyone. It seemed more of a way for McCartney to challenge himself as a composer.
21. “Uncle Albert/Admiral Halsey” (1971)

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There’s almost a Pink Floyd-esque sound to the first part of McCartney’s single off his solo album Ram. To no surprise, it became a No. 1 hit for McCartney — his first as a solo artist. It also became his first gold record since the disbandment of The Beatles. He ended up winning a Grammy for the song.
20. “The Long and Winding Road (1970)

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This was the final No. 1 song for The Beatles. The band had broken up shortly before it’s release, but that didn’t stop the success from coming. While the song is among The Beatles’ most beautiful offerings, McCartney was not a big fan of producer Phil Spector bringing strings into the mix. McCartney thought that the stings would essentially drown out the work of the actual band. It’s still a moving piece on the group’s swan song.
19. “Here, There and Everywhere” (1966)

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One of the gems off Revolver, many believe this is one of the Beatles’ most underrated tunes. McCartney, reportedly, considers it special to him on a personal level. Lore also has it that McCartney’s inspiration, at least somewhat, came from The Beach Boys’ hit “God Only Knows.” Listening to the song a few times, and one can certainly see the similarities in flow.
18. Ob-La-Di, Ob-La-Da (1968)

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Want to see crowd participation at its finest, be at a McCartney solo gig when he plays this one. “The White Album” track was not necessarily praised by critics at the time, but it has become a favorite to the casual Beatles fan looking for a good time. It’s also seen plenty of pop culture prominence, from countless covers to a Patti LuPone-led version for the theme song of her late 1980s-early-‘90s series “Life Goes On,” which is a line from the song.
17. Love Me Do (1962)

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Though well known for John Lennon’s work on the harmonica, this was one of the earliest Beatles songs written by McCartney. It’s also one the band’s songs that has been released in several different versions, including one with Pete Best on drums. The track’s release in the United States came almost two years after (in 1964) it’s original one in the United Kingdom.
16. “Too Many People” (1971)

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The B-side of “Uncle Albert/Admiral Halsey,” and McCartney’s personal dig at former Beatles bandmate Lennon and John’s wife, Yoko Ono – for their dominance in the direction of the band. ‘Too many people preaching practices. Don’t let them tell you what you wanna be.’ Are just two of the lines McCartney directed toward Lennon, who would respond later that year with “How Do You Sleep?” off Imagine.
15. “Eleanor Rigby” (1966)

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McCartney and the Beatles were in experimentation mode at this point in their careers. Strings and conceptional lyrics, the song was noticeably different from the group’s early pop favorites. The Revolver hit left some music fans wondering just who are these people that Paul and band are telling us about. It’s only 2 minutes, 8 seconds long.
14. “Penny Lane” (1967)

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McCartney wrote this song about his upbringing in Liverpool, thus touching on some personal nostalgia. The single hit No. 1 in the United States and was included on the U.S. version of Magical Mystery Tour. The song features a trumpet, flute and hand bell, all demonstrating how innovative the band was becoming.
13. “Live and Let Die” (1973)

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The theme song of the 1973 James Bond film of the same name is probably the most popular of any material McCartney released post-Beatles. Just like a Bond movie should be, the song is fast, loud and over the top. McCartney’s concert version of this Wings’ classic is the same way – times 10. Complete with explosions and fireworks, even Sir Paul himself knows it is a bit too grandiose.
12. “I Saw Her Standing There” (1963)

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Like many of those early Beatles songs, this one often sent teenage girls into a frenzy. Interestingly, the cut was released in America as the B-side to “I Want to Hold Your Hand.” McCartney claims to have been inspired by Chuck Berry while putting the song together. It would be over two decades later that American pop singer Tiffany found success throughout suburban shopping malls with her version.
11. “We Can Work It Out” (1965)

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It’s one of the few Beatles songs that McCartney and Lennon fully collaborated on, but certainly qualifies to be on this list. McCartney’s words offer the optimistic view of a potentially lost relationship, while Lennon delivers a more realistic view with his ‘life is very short’ line. Songs like this from the duo were somewhat rare, but certainly worth celebrating.
10. “Jet” (1974)

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One of the hits off Wings’ uber-successful Band on the Run album, it’s also one of the more confusing, in terms of lyrics, of any in McCartney’s catalog. Whether it’s about a jet-black dog or even a pony, as legend goes, it’s still a fun, up-tempo single. Which totally encapsulates the state of the arena-rock scene that defined much of the second half of the 1970s.
9. “Helter Skelter” (1968)

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With this one off “the White Album,” it’s the closest the Beatles came to a heavy-metal sound. It seemed to work, and has often been cited as a major influence on countless hard-rock acts such as Motley Crue. Mostly written by McCartney, the song, unfortunately, was also a favorite of notorious psychopath Charles Manson.
8. “Nineteen Hundred and Eighty-Five (1974)

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Another gem off Wings’ Band on the Run, this is the hard-charging end to McCartney’s best collective album with Wings. From McCartney’s pounding piano, Denny Laine’s brilliant guitar work and the out-of-this-world, space-age climax, it remains one of his most innovated efforts spanning both his career with the Beatles or beyond.
7. Band on the Run (1974)

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One of McCartney’s most successful cuts in the years following the demise of the Beatles. The song reached No. 1 in the United States. It features three uniquely different parts, with the title of the song not appearing until the final third. Yet everything comes together, and proves that McCartney could deliver no matter who is at his side.
6. “Hello, Goodbye” (1967)

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The song was initially released as a single, and the first following the death of the Beatles longtime manager Brian Epstein. The track received mixed reviews from critics, as the group was getting more adventurous with its music. However, a pop-tinged tune like this could helped make the transition a little easier for the listener, and has aged relatively well.
5. “Golden Slumbers/Carry That Weight/The End” (1969)

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The three-song conclusion to the lengthy Abbey Road medley ends in poignant fashion, but before taking the listener on an interesting journey. The closing lines of “The End” that state: ‘And in the end, the love you take is equal to the love you make,’ fit in well with the Beatles’ overall dysfunction as a group and eventual break up. This collection of unfinished songs remains as powerful today as it did back in the late 1960s.
4. “Hey Jude” (1968)

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One of the most popular songs of all-time, let alone by the Beatles. McCartney wrote it as a way to help Lennon’s son, Julian, deal with his parents’ break up. The track spent nine weeks atop the U.S. charts, the longest stint for any song by the band. The collective ‘Nah nah nah nah nah nah, nah nah nah, hey Jude,’ is a highlight of McCartney’s live shows.
3. “Yesterday” (1965)

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Considered one of the most covered songs in music history, “Yesterday” showcases McCartney’s lighter, melodic side. To many, it’s the Beatles’ greatest song, and often considered the best of all-time in any genre. Of course, it continues to be a must for McCartney’s live shows and perhaps the song at the forefront of his legacy as a songwriter.
2. Maybe I’m Amazed (1970)

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The song that McCartney wrote as the Beatles were headed for a break up, and one inspired by the help then-wife, Linda, gave him during the ordeal. It was released on his solo debut McCartney, but the track truly took off after its inclusion on the Wings over America live album from 1976. While many would disagree, this song stands strongly alongside any of McCartney’s works with the Beatles.
1. “Let It Be” (1970)

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Written before the band’s swan song album of the same name was released, it’s poignant and timely of the Beatles official break up that would follow. McCartney’s masterpiece has endured several versions and remastering. While die-hard Beatles fans probably feel it has been overplayed, it’s still the perfect bittersweet representation of the band’s farewell.