Trying to come up with a ranking of the best albums of all time is hard enough, what with there being so many out there released over numerous decades. That medium, as a way to collect music, isn’t quite as old as the notion of a feature film, and then early novels came out so much further back in time still, but there do remain a great many albums regardless.

So, when you try to do some kind of massive ranking for songs, it feels even more daunting. An artist might have a dozen albums, or several, or maybe several dozen, and then on each album, you usually get more than a handful of songs, meaning artists will generally have dozens (or even hundreds) of recorded songs to their name. There are too many great ones to choose from, and so any ranking of the best songs of all time will have omissions, even if someone had the patience to do a list that was “The Top 10,000 Songs of All Time.” What you’ve got here is only 25. One song per artist, as a limit. Sorry in advance for all those omissions.

25

“Tangled Up in Blue” (1975)

Bob Dylan

To kick things off with an artist who has an overwhelming number of songs, here’s Bob Dylan. He’s been active since the 1960s, and during that decade, he was pumping out at least one album a year. Things slowed down a little as he got a bit older, but still, not that slow. There are several hundred, and of the bunch, “Tangled Up in Blue” might well be his very best.

It’s the opening track on Blood on the Tracks, which is easily the best post-1960s Dylan album, and possibly his greatest of any decade, too. The storytelling here is as great as you’d expect from Bob Dylan at the top of his game, with it tackling love and relationship troubles, but in that usual poetic and slightly abstract Dylan-esque way. His 1960s songs, especially the politically and socially conscious ones, might sometimes be celebrated even more for their lyrics, though Bob Dylan showing he could write about more abstract and emotional things here, on Blood on the Tracks (and especially in “Tangled Up in Blue”), demonstrated even further range for the equal parts legendary and enigmatic artist.

24

“Fairytale of New York” (1987)

The Pogues featuring Kirsty MacColl

The best Christmas song of all time also happens to include the line “you scumbag, you maggot,” and then another word that rhymes with “maggot” that probably can’t be mentioned here. And then there’s some other language in “Fairytale of New York” that’s not very Christmassy. But that’s The Pogues for you, with this song – the most iconic the band ever made – being beautiful at the same time that it’s kind of rough and crass. Very Pogues.

Also, it’s a duet, with the controversial parts being as a result of an argument between the two characters being “played” by the lead singers: Shane MacGowan (the band’s lead singer) and Kirsty MacColl (as a guest vocalist, whose contribution to the song has to be acknowledged). “Fairytale of New York” might be more of an anti-Christmas song, in all honesty, but depending on where you are in the world while celebrating that time of year, you may hear it in rotation with the likes of WHAM’s “Last Christmas,” John Lennon and Yoko Ono’s “Happy Xmas (War Is Over),” and, yes, maybe even Mariah Carey’s “All I Want for Christmas Is You.”

23

“This Must Be the Place (Naive Melody)” (1983)

Talking Heads

“Tangled Up in Blue” was a change of pace lyrically, to some extent, for Bob Dylan. The same can possibly be said about “This Must Be the Place (Naive Melody)” for Talking Heads. The band’s music hadn’t really been political in the same way Dylan’s had, but most of the band’s songs that came out before “This Must Be the Place (Naive Melody)” were not love songs, and were more focused on… like, society? And general anxiety within society. This was a band that called one of their albums Fear of Music, after all.

Yet “This Must Be the Place (Naive Melody)” is an all-timer of a love song. It is genuinely sweet and romantic, while still retaining a little by way of Talking Heads’ quirkiness and eccentricity. It’s also tempting to call the performance of the song in Stop Making Sense a highlight of the movie, but that movie is almost nothing but highlights, so it’s hard. It’s one of many great songs performed in that concert movie… how about that?

22

“Juicy” (1994)

The Notorious B.I.G.

The Notorious B.I.G. might have reached further heights artistically, had he not been cut down when he was still so young, but as it stands, “Juicy” is his crowning achievement. Then again, it might’ve been hard to top, and there aren’t too many hip-hop songs released since, by other artists, that come all that close. “Juicy” is infectious, and then lyrically, it’s also tremendously emotional while being confident and triumphant, too.

It’s a song where The Notorious B.I.G. celebrates what he’s done, but without coming across as purely boastful or tacky. It is the centerpiece of Ready to Die, which is a fairly strange listen from start to finish, at least for an album considered as such a classic (what with some pretty gonzo interludes and then such a dark closing track… but at least “Juicy” is all good, baby baby).

21

“Pyramids” (2012)

Frank Ocean

While Blonde is the ultimate Frank Ocean album, being an even stronger listen from start to finish than Channel Orange, it’s Channel Orange that contains what’s arguably the ultimate Frank Ocean song. That song is “Pyramids,” and it has enough stages to feel like a few songs packed into one, being like an R&B “Bohemian Rhapsody,” and maybe just better than “Bohemian Rhapsody” generally, too.

Lyrically, “Pyramids” is also adventurous and willing to go to a bunch of different places, fitting the mash-up of genres heard throughout. It sounded phenomenal back in the 2010s, of course, but it feels like the kind of thing that’ll endure and probably sound even better once a few more years (or even decades) have passed by. It’s the most recent song in this ranking, and more than deserves a place here, among the all-timers, relative recency be damned.

20

“Live to Tell” (1986)

Madonna

The high-energy Madonna songs are fun, no doubt. If you’re in a certain mood (like, a good one, in other words… lucky you!), they’re the ones you’re probably going to gravitate towards. Even Ray of Light, which is fairly mellow, has the high-energy title track standing out as a highlight. Confessions on a Dance Floor feels like a continuous party disguised as an hour-long album, and then her self-titled debut is also very bubbly and infectious.

True Blue, though, her third album, is a bit more mature, and you definitely hear that on “Live to Tell,” which is an early ballad from the artist. There are other songs on True Blue that are poppier and kind of danceable, but the introspection and moodiness heard in “Live to Tell” is significant, and really did suggest a level of depth Madonna kept exploring in subsequent albums (especially the aforementioned Ray of Light).

19

“Us” (2003)

Regina Spektor

The best song from an album named after a term from a great book (album: Soviet Kitsch, and book: The Unbearable Lightness of Being), “Us” feels very special, and in ways that are hard to describe. Regina Spektor tapped into something next-level here, and it’s not like she doesn’t have other good songs, but there’s something about “Us,” and not in a Daft Punk way.

“Us” is lyrically odd, since it manages to be about love (probably) and politics at the same time, and then it’s also very abstract at times, even if you’re able to quite intensely feel what it’s going for. Spektor’s vocals and the production of the song might be the parts that sell that a little more, yet there are still so many lines in “Us” that, once heard, are hard to forget.

18

“Come On Eileen” (1982)

Dexys Midnight Runners

“Come On Eileen” went to #1 in a bunch of different territories, so of all the songs here, it’s probably one of the ones you’ve had the best chance of hearing at some point. Possibly, you might’ve heard it more times than you wanted to. It’s also got some instrumentation that’s unusual for a hit song, but it works, and Dexys Midnight Runners do indeed get away with it. Still, if you don’t like hearing a banjo and accordion, among other instruments, in your pop music, maybe it’s not going to be for you.

If you’re on board with that, though, “Come On Eileen” is everything. It’s got one of the best choruses maybe ever, and then the bridge (the “ta-loo-rye-aye” part) is also immense, with the build-up back to the final chorus and all. The grandness and sweeping quality of the song emotionally, and then what it does instrumentally, make it easily among the best of the best chart-topping songs of the 1980s.

17

“All My Friends” (2007)

LCD Soundsystem

As was sort of cool at the time, (in the 2000s, and for rock-adjacent music), “All My Friends” has a postmodern and meta aspect to it, unavoidable when the first line is “That’s how it starts.” LCD Soundsystem kind of subverts this at the same time, because “All My Friends” technically starts with just a piano riff, and then some other instruments gradually join in, and then the line “That’s how it starts” is heard after one minute and 20 seconds. Plenty of other songs are already half over by that point and all.

That build you get throughout the instrumental intro is continued once James Murphy starts singing. The song gets a little louder and more emotionally intense, bit by bit, and the effect is very cathartic, and also very sad. Whether you get more catharsis or sadness out of it depends on your mood whenever you listen. Of all the songs that focus on middle-aged angst, or an approaching sense of middle-aged angst (admittedly not many, but still), “All My Friends” might well be the best.

16

“Dancing Queen” (1976)

ABBA

Arrival houses so many great ABBA songs, and though The Visitors might be conceptually more interesting, and a little more consistent, as an album, it’s hard to overlook Arrival when it comes to crowning an album as ABBA’s best, in large part thanks to it having “Dancing Queen.” You might reject disco, as a genre/sound, yet deep down, you know you secretly like “Dancing Queen.” You don’t have to admit it to anyone, don’t worry, but at least admit it to yourself. Be free. Be liberated.

It’s right and proper to feel liberated when that’s the main emotion this song inspires. “Dancing Queen” is as bouncy and euphoric as pop songs get, and pretty much the whole appeal of ABBA can be found within this single track. A song having “dancing” in its title and not feeling inherently danceable would be kind of embarrassing, but thankfully, “Dancing Queen” has never had – and will never have – to worry about that.