There are rules that come with writing individual songs a good deal of the time, and even if rules aren’t made to be broken, like literally, some definitely can be broken. Rules being broken can lead to things feeling exciting and cooler. Maybe there’ll be new rules. Maybe someone didn’t follow an old rule and now things can be done better. And how does it sound? This is music being talked about here, by the way. It’s gotta sound gooooood.
The following songs sound, if not goooood, then definitely gooood. Nothing boring and goood here, so don’t you worry. But speaking of good songs, however you want to spell good, the songs here are good, but they’re being ranked highly here because of their ambition. Quality is great, and it helps, but those songs with big ideas and aspirations that paid off, giving listeners something unique and bold and game-changing… that’s what matters. Also important: long songs that stay interesting for a long time, and there’ll be an effort to only highlight one song per artist (even making sure to highlight 10 artists, no one is going to be happy with the extent of the omissions here, so, apologies in advance).
10
“Jungleland” (1975)
Bruce Springsteen
It wouldn’t be right to praise “Jungleland” without first giving an honorable mention to “New York City Serenade,” because that was a nearly 10-minute-long closing track on a Bruce Springsteen album before “Jungleland” closed Born to Run. Both songs are incredibly cinematic and effective as epic final tracks, but “Jungleland” has more variety and kind of touches upon a greater number of emotional beats throughout.
While Springsteen might have some songs that are even better, few can claim to be as ambitious.
Structurally, this one starts quiet, gets big, then goes mellow again, slows down to a crawl, and then finishes big again. 10 minutes is a lot of time to play around with for one song, sure, but it still does an impressive amount of things with all that time. While Springsteen might have some songs that are even better, few can claim to be as ambitious, and all that’s before even touching upon how remarkable “Jungleland” is on a storytelling front, too.
9
“Purple Rain” (1984)
Another huge song, but yes, “Purple Rain” does have to be mentioned. Even if you’re talking about the best songs of all time, regardless of ambition or an overall epic scope, it’s still commendable and easily among the all-time greats. Prince made a version that was even bigger, too, because the “Purple Rain” on Prince and the Revolution: Live (1985) goes for over 18 minutes, while the studio version is “merely” about nine.
Either way, you lose track of time listening to the titular song from Prince’s greatest album, and finishing such a great album on such a high after eight great tracks was quite the accomplishment. Prince did indeed go bigger and more epic here with this ballad, making it the perfect ending to a perfect album, and it’s a worthy pick for the title of “most ambitious song Prince ever recorded.”
8
“Dance Yrself Clean” (2010)
LCD Soundsystem
LCD Soundsystem have always seemed to love alternative sorts of bands from decades earlier, being a newer band (the 2000s and 2010s were a while ago now, though), that’s a good one to listen to if you want some exposure to those older sounds. LCD Soundsystem still does have an original sound to some extent, but it’s the Quentin Tarantino approach of getting so many influences and blending them all into something unique or postmodern in nature.
There are a good many lengthy LCD Soundsystem tracks out there, with “Dance Yrself Clean” being one of the longest. Here, what’s most impressive, though, is how much this song shifts between sounding quiet and loud, and the way it plays around with dynamics, all in a very cathartic manner. It’s an especially great song if you see a recording of LCD Soundsystem playing it live, but even the studio version here is still incredible.
7
“Close to the Edge” (1972)
The song “Close to the Edge” was probably close to spilling off one side of the vinyl album of the same name, since “Close to the Edge” is about 19 minutes long, and plenty of vinyl sides only hold up 20 minutes of music… or less. There are sections here, like some kind of symphony almost, but it’s rock, and so there are vocals, and you’ve got some experimental instrumentation thrown in there, it being the style at the time and stuff.
Yes would go on to make some even bigger albums, with Close to the Edge and its three tracks being dwarfed by the four songs on Tales from Topographic Oceans, which was a 1973 album that ran for 80 minutes, and the songs were of comparable lengths, all being either a little over or a little under 20 minutes. “Close to the Edge,” though, is better written, structured, and paced, not to mention standing as the older song and being more groundbreaking in that regard as a result, too.
6
“Starless” (1974)
King Crimson
You might know Robert Fripp more from his collaborations with Brian Eno and David Bowie, and regarding the latter, that’s probably where you’re more likely to have heard him, but King Crimson is the band he’s done the most with, since he founded it and has been its only constant member. And King Crimson might not be a household name, but if you’re into progressive rock, then they couldn’t be more legendary and influential.
Of course, you’re best off listening to some of the band’s best albums in full, with In the Court of the Crimson King being a good starting point, but Red might be an even stronger album. It helps that it concludes with the best-ever King Crimson song, “Starless,” which is impossibly expansive and monumental for a perfect 12 minutes. You really get a whole album’s worth of ideas and sounds crammed into a single remarkable track here.
5
“Runaway” (2010)
Kanye West
“Runaway” is at the center of My Beautiful Dark Twisted Fantasy, and then that’s an album which itself pretty much sits in the center of Kanye West‘s whole discography. Technically, his whole discography to date, but like, probably forever. West’s been on shakier ground critically and culturally in the last few years, but still, My Beautiful Dark Twisted Fantasy is My Beautiful Dark Twisted Fantasy, and “Runaway” represents that great album at its greatest.
Lyrically, it’s a very introspective and brutally honest song, and those all-time great lyrics are backed up with everything the song does interesting on an instrumental front, and then that extended intro probably shouldn’t work as well as it does, but it feels perfect anyway. It scores some extra points by way of ambition because of its length and the way it shifts into something so odd but fitting for its final few minutes, yet even if you look at the song regardless of length, it’s still a pretty monumental achievement artistically.
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“Echoes” (1971)
Pink Floyd
There’s no lack of ambition to be found throughout the Pink Floyd discography, and that’s especially so if you hone in on the band’s albums from the 1970s, because that decade saw the release of The Dark Side of the Moon, Wish You Were Here, Animals, and The Wall. Those are probably the big four, and they’re all grand progressive rock albums (alongside dipping into some other genres), but if you want a big five, you can throw Meddle in there as well.
That one came out earlier in the decade, and it houses Pink Floyd’s longest and grandest track: “Echoes.” This one is literally half the album, like “Close to the Edge,” because “Echoes” takes up the whole of the album’s second side, running for over 23 minutes, while Meddle overall is a bit over 46 minutes long. If that’s cheating a bit, because it’s the length of multiple songs already… uh, sorry. But it’s still technically one song, and there is so much going on in this one song, so it’s worthy of praise here, for present purposes.
3
“A Day in the Life” (1967)
The Beatles
It’s a clichéd pick perhaps, since the amount of praise “A Day in the Life” has gotten over the decades is a bit exhausting, and there is probably even a bit of exasperation that comes with seeing yet another person declare it the best of all The Beatles songs. That’s not being done here, though, necessarily. “A Day in the Life” is here because it’s probably the most impressive of all the songs the band ever did, and that counts for a lot when the band you’re talking about is The Beatles.
While there is no single song by The Beatles that captures everything the band was capable of, the closest one track comes to doing that is probably “A Day in the Life.” There is a real contrast between the John Lennon and Paul McCartney parts that you don’t get on many other Beatles songs, it’s one of the band’s longest tracks, and then it does have a genuinely surprising final minute or so (all the while being timelessly unsettling, and hard to describe without just recommending someone listen to the whole thing for themselves).
2
“Impossible Soul” (2010)
Sufjan Stevens
No song tries to put all the songs into one song in quite the same way as “Impossible Soul.” This Sufjan Stevens track is 25 minutes all up, and it’s another song that might as well be a mini-album. It closes The Age of Adz, which is a very eclectic and experimental album, and then “Impossible Soul” is the culmination of all that wonderful chaos, going far to keep the head-spinning colorfulness of it all going.
It’s absolutely overwhelming when it starts quiet, glitches out for a while, then gets booming and cathartic, before collapsing and getting a little quiet once more, and then being ever-so-fragile as it finally concludes all those minutes later. All that only captures the truly impossible journey that “Impossible Soul” takes you on, but it’s such a massive accomplishment, it’s hard not to sit back and just feel hugely impressed at the whole unwieldy thing.
1
“Bohemian Rhapsody” (1975)
It’s the obvious pick, but it’s deserving, so here it is: “Bohemian Rhapsody” by Queen. As some of the other songs from the 1970s here demonstrate, this was not the first song to be twice as long (or even longer) than your average song, and it can’t even be counted as the first song to successfully have different parts that sounded distinct while all adding up to one coherent whole, as “A Day in the Life” makes clear. That one did beat “Bohemian Rhapsody” by almost a decade, too.
Where “Bohemian Rhapsody” shines, though, is having such a wild collection of genres/types of music blended into one track. Like a lot of the songs here, you’d look at this on paper and say it would never work in execution, yet here the song is regardless, standing as one of the most famous and beloved of all time. If you’re after something groundbreaking, iconic, and approachable, even with it being so strange, songs don’t really get much more impressive.
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Freddie Mercury
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Brian May
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Roger Taylor
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Joseph Mazzello
John Deacon
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