Five of Paul McCartney’s saddest solo songs

It’s hard to find another artist more optimistic than Paul McCartney. Compared to the other Beatles and almost every other songwriter that has walked the Earth, Macca couldn’t have more upbeat tunes unless he had literal sunshine projecting out of his ass every time he played a concert. Despite being the living embodiment of Eric Idle’s cheery character from Life of Brian, McCartney could have his fair share of downer moments as well.

Throughout his career, McCartney never claimed to be happy all the time, and some of his most emotional songs are when he decides to put his cheeriness on the shelf for a little while to let everyone know how he’s feeling. They aren’t always comfortable listening, but it’s usually interesting to see him open himself up in a way that no one had seen before.

That doesn’t discount the songs that he made during his Beatle years, either. Throughout his time with the Fab Four, McCartney could match John Lennon’s cynical streak when he wanted to, either singing about his personal struggles or putting a character in its place by singing about what they’re dealing with daily.

McCartney doesn’t need to prove his worth to anyone anymore, but his morose tunes remind people that he was more than just a one-trick pony. This was a man who had a lot of dark things on his mind, and when they did decide to rear their head, it caught many of us off-guard, knowing that this was the man behind something as silly as ‘Maxwell’s Silver Hammer’.

Paul McCartney’s saddest solo songs:
5. ‘I Don’t Know’
After going through half a century in the public eye, it would be easy to think that McCartney has everything in his life figured out. He doesn’t seem to even breathe the same air as the rest of us, so it makes sense that he could just go through life without a care in the world. But even after years of experience and performing every genre under the sun, he’s here to remind us that even he’s insecure on ‘I Don’t Know’.

Despite Egypt Station being one of the more upbeat albums that Macca has released as of late, hearing him talk about his own struggles from day to day is a breath of fresh air from him. Looking back on the kind of life that he has led and the countless hits that he has put on the charts, it’s almost a little bit reassuring knowing that even one of the biggest pop idols the world has ever known is still having the same internal questions that we all have.

4. ‘Little Willow’
McCartney is usually the one Beatle everyone goes to for a pick-me-up. Even though he’s been able to have his downer moments, one of his greatest strengths is doing exactly what he said in ‘Hey Jude’: taking a sad song and making it better. But sometimes life doesn’t have all the right answers, and when Ringo Starr’s wife Maureen passed away, McCartney penned this beautiful tearjerker to help Starr’s kids make sense of their mother not being around anymore.

While death is never easy to come to grips with, McCartney’s tone sounds like a concerned uncle trying his best to make the most out of the situation that he can. Although nothing could ever replace someone in their lives, hearing him sing about how no one is out to break their heart and that they should keep moving on is actually the best advice possible. There’s no way for someone to put a positive spin on death but leave it to McCartney to take a morose song and let everyone know that the world hadn’t ended.

3. ‘Dear Friend’
The fallout of The Beatles was bound to be incredibly messy the minute that everyone started hurling abuse at each other. No one had to leave with warm feelings, but when Macca released ‘Too Many People’ and John Lennon retorted with ‘How Do You Sleep’, most people thought that the songwriting team legitimately hated each other for years on end. Whereas those first songs were pure musical frustration, ‘Dear Friend’ was when Macca seemed genuinely hurt.

Now that he had a new band by his side, McCartney sings about Lennon as if he’s trying to mend the fences of his relationship. Even though the song itself has a positive message, McCartney sounds like he’s on the verge of tears behind the sad accompaniment, as if he knows that there’s a slim chance that he will ever be on speaking terms with his best mate ever again. Thankfully, they did eventually patch things up, but if fans didn’t know any better, they may as well have seen a musical relationship die right before their eyes.

2. ‘The End of the End’
Most artists have to face mortality at some point or another. No one is going to be around forever, so it’s better to try and bow out gracefully before time comes looking for you on the other side. Even after another decade on from Memory Almost Full, McCartney delivered one of his most stirring songs on ‘The End of the End’ where he faces down the life that he has lived for over 60 years.

While Blackstar by David Bowie is a more immediate version of facing mortality, McCartney is looking ahead on this song to the day that he passes away, saying that he would rather have jokes be told and people laughing about what he gave to the world. Then again, no one would want it any other way, right? McCartney was known to be the light in the darkness throughout his career, so what better way to reminisce than to hear all of the great fun people had with his music?

1. ‘Here Today’
It’s hard to really think of Paul McCartney’s career without the help of John Lennon. He has had more road miles as a musician without his writing partner by his side, but nothing can take away that borderline telepathic bond they had in the group’s early years. Once Lennon was shot in cold blood outside his apartment building, though, there was no way that McCartney could sidestep his grief anymore.

Written as an imaginary conversation that he wanted to have with Lennon, McCartney is practically tearing up as he’s singing the song, thinking that he never had the chance to say everything that he wanted to his old mate. With the help of Beatles producer George Martin, this is like the friendship companion to a song like ‘Yesterday’, where McCartney thanks Lennon for being a part of his time on this Earth. And who knows? Maybe someday when they have long since departed from this world, perhaps they can make beautiful music together again on the other side of reality.

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