Unfortunately, as much as I've tried to delve into the deeper meanings of their songs, I've never been one to overly analyse (I do faithfully, keep the incredible SongMeanings site open at all times though) their lyrics. Needless to say, I'm a Gilmour guy in the eternal Gilmour-Waters #youprefer debate. So the following list should really come as no surprise.
I'm not a huge fan of early Floyd. Piper At The Gates of Dawn had it's moments of fun for me, but that's like a cheap circus before moving onto the main thing. The golden era of Floyd for me, as for millions of others, remain the Dark Side Of the Moon -> Wish You Were Here -> Animals -> The Wall era.
So here are the top 20, in reverse order (and YouTube videos!)
20] Atom Heart Mother Suite : After you painfully move through albums 2, 3 and 4 (yeah, I'm not a fan of that era), this track hits you. First - with its sheer length of over 23 minutes. Then, the synth riff. Then, as you read what it's about, the various 'movements'. This set the tone for another epic of similar length an album down the line, as far as listening to the discography goes. The video is linked to a 10 minute live performance in '72, by the way.
19] The Great Gig In The Sky : The first time I saw this was during a PF Tribute show in Thrissur of all places. I was blown away by a lot of songs (I was listening to Floyd - rendition or otherwise - for the first time) but this one in particular mesmerized me. Whatay vocals by Clare Torry.
18] Sorrow : As much a Gilmour fan as I am, I really don't think much of A Momentary Lapse of Reason. This track to me is the album's saving grace. I just love the way it starts, and am willing to overlook the fact that it meanders off lazily like many tracks on the album.
17] Interstellar Overdrive : Among the weirdness of the first album lies this absolute gem. It's hard to think of anyone but Syd coming up with something like this, and is surely one of the definitive guiding moments for the band.
16] Breathe : We were led to believe that the first album was a whimsy of their then leader. The next few albums, they struggled to find a voice. They found their sound with one of the most epic tracks ever from Meddle. But something was still missing. The moment you hear the chatter on Speak To Me, you know something's gonna give. Breathe kicks in. Pink Floyd, ladies and gentlemen, had arrived.
15] Hey You! : Fantastic standalone track from a brilliant concept album.
14] Welcome To The Machine : Fantastic lyrics dissing the record company establishment. Lovely atmosphere. Space-age effects that were different from Piper because they sounded mature and fit in.
13] Dogs : Their last true 'epic'. The whole Animals album showed Pink Floyd at their peak - great musicmanship, writing and production. While I like Pigs better, this was the more hard-hitting. Roger Waters at his lyrical best. I mean, sample these:
And after a while you can work on points for style,
like the club tie and the firm handshake,
a certain look in the eye and an easy smile.
You have to be trusted by the people that you lie to,
so that when thy turn their backs on you,
you'll get the chance to put the knife in.
Simple, yet killer.
12] Wish You Were Here : The title track from their 9th album has #win written all over it - from the concept of an album for Syd to the radio intro. Easily their most sing-along track, as proved by its overkill by college bands and pretty much any group with an acoustic guitar.
11] Pigs (Three Different Ones) : Waters has never sounded more vehement. For the delicious lyrical output alone, this track deserves a listen.
10] Another Brick In The Wall - Part 2 : The song everyone knows. What a tragedy, however, that they do not know how it fits in to the rest of The Wall. Featuring one of Gilmour's sweetest solos and one of rock music's most recognizable basslines.
09] Coming Back To Life : I guess here's where I lose the Waters fanboys. Sorry, chaps. Those guitar solos are just too good to ignore.
08] Have a Cigar : Again, Floyd at their peak from (what I think is) their finest album. The intro is enough to kick you in the tum, and then the fantastic vocals by guest singer, Roy Harper. Like Led Zep would later title a song, hats off.
07] Marooned : My favourite of the Floyd instrumentals. Gilmour again showing signs of genius, which just makes the world sigh wondering what would have been had Waters' ego not got the better of him.
06] Shine On You Crazy Diamond (Parts I - IV) : And each member of the band does shine here, in this tribute to their first leader, Syd Barrett. That first guitar note is probably the most 'anticipated' in the history of rock. Bliss.
05] Time : With good earphones (yay, IE7!) you can bring out the true sonic brilliance of the intro. But you don't need that to realise this is a monumental track from a band that knows it's found its purple patch. With one of the most dry takes on modern life, which still remains relevant today, Floyd were making a statement. One that would continue for the next few albums as well.
04] Money : And a couple of tracks after Time, comes this. Show me one person who hasn't been taken away by the 7/8 bassline or the 'money-sounds-loop'. Or the sax. Brilliant, brilliant track.
This brings us to the final 3.
03] High Hopes : That guitar solo. Period. (for best results, see the P.U.L.S.E version)
02] Echoes : After muddling around for 5 albums and 5 tracks, just having heard the terrible 'Seamus', a first-timer could be forgiven for giving up on Floyd. And then - the piano. THAT piano sound. Only Pink fucking Floyd could have pulled off playing the same note for over a minute. You KNOW from then that the track is going to be freaking epic, you realise this band could actually mean something. And when you hear THIS paragraph:
Cloudless everyday you fall upon my waking eyes
Inviting and inciting me to rise
And through the window in the wall
Come streaming in on sunlight wings
A million bright ambassadors of morning
there are no more doubts. But it all starts with that piano note.
01] Comfortably Numb : While there's always the temptation to move away from the 'expected' #1 in order to look 'cooler' and 'more educated', I'd still rate this as their best ever song. For a variety of reasons. The lyrics. The music. The concept. The video. The way it's sung. The arrangement. One of the greatest guitar solos of all time. The last great song by Waters/Gilmour. Again, overkilled by bands left right and center (including a couple I was involved in, who killed it rather than overkilled it) but still revered by Floydfreaks the moment that first Bm kicks in. Again, best results - P.U.L.S.E version.
Any Floyd list, however, including this one, does tremendous injustice to the masterpiece that is The Wall, where each track lays the foundation for the next. Comfortably Numb sounds freakin' better when preceded by the 2 tracks that come before it, as does ABITW-2. Even if you're going to just listen to these 20, I'd recommend giving The Wall an entire listen, and looking up the lyrics as you go.
There you go, will probably come up with Led Zep or something in a while.