▶ Listen on Spotify, Apple Music or YouTube
3. Wings: “Arrow Through Me”
The pain of a lover’s betrayal is barely contained in one of McCartney’s most chromatically devious songs, from the 1979 Wings album “Back to the Egg.” The song nods toward the jazzy R&B of Stevie Wonder and Earth, Wind & Fire, with a clavinet among the keyboards and a jagged horn-section riff. (It was also funky enough for Erykah Badu to draw on in 2010 for her “Gone Baby, Don’t Be Long.”) McCartney’s vocal pretends to be nonchalant, hopping into falsetto, but it keeps shading into rawness. — PARELES
▶ Listen on Spotify, Apple Music or YouTube
4. Paul & Linda McCartney: “Oh Woman, Oh Why”
This B-side to the aforementioned 1971 single “Another Day” is one of the odder (and darker) entries in McCartney’s vast catalog: A bluesy rocker about a jealous man who shoots his cheating wife — complete with gunshot sound effects! — that a possessed McCartney screeches from the tippy-top of his vocal register. I cannot think of another Paul McCartney song on which he sounds this much like Robert Plant, or, occasionally, Donald Duck. — ZOLADZ
▶ Listen on Spotify, Apple Music or YouTube
5. Paul McCartney: “House of Wax”
McCartney verged on goth in “House of Wax” from his 2007 album, “Memory Almost Full.” Over tolling minor piano chords, soon to be joined by thundering drums and brooding strings, he sang an apocalyptic scenario: “Lightning hits the house of wax / Women scream and run around / To dance upon the battleground.” He finds momentary uplift when he sings about “the answer to it all” — but that answer is “buried deep below a thousand layers,” and the song concludes as a dirge. — PARELES
▶ Listen on Spotify, Apple Music or YouTube
6. Paul McCartney: “Deep Deep Feeling”
One true outlier even in a catalog full of experiments, “Deep Deep Feeling” — from the 2020 “McCartney III” — sets aside verse-chorus-verse form to ride a stark beat and an agony-and-ecstasy mood: “the deep deep pain of feeling” that goes with loving someone “so much you feel your heart’s gonna burst.” The track is spooky and wide open, beginning with just a stark beat and introducing instruments and vocal — all performed by McCartney — to assemble a complex edifice of call-and-response, only to silence it completely and return with a guitar-strumming coda. It’s McCartney going wherever his ears lead him. — PARELES
▶ Listen on Spotify, Apple Music or YouTube
7. The Beatles: “Eleanor Rigby”
Quite possibly the most crushingly sad Beatles song ever, “Eleanor Rigby” is a compassionate, vividly detailed meditation on loneliness and an ode to the sort of person who is not usually the subject of a pop song. Most Beatles compositions were collaborations, of course, but by almost all accounts “Eleanor Rigby” was McCartney’s baby — albeit with small but crucial contributions from the other band members and, in this particular case, the Quarrymen’s former skiffle player Pete Shotton. As McCartney put it in a delightful 2021 New Yorker essay about the creation of “Eleanor Rigby,” “it did feel more like a breakthrough for me lyrically — more of a serious song.” He added, with just a touch of pride, “Allen Ginsberg told me it was a great poem, so I’m going to go with Allen. He was no slouch.” — ZOLADZ
▶ Listen on Spotify, Apple Music or YouTube
