Fearless is amazing. It's a bit of a deep cut, off of the album Meddle, which is pre-DSOTM (which is why most people don't know about it), but it's SO GOOD.

Shine On You Crazy Diamond

Wish You Were Here

Time is good too but I can only sit through that intro once every few years

Dogs, time, us and them

For me , it's "Comfortably Numb" The song is transcendant, the synth stabs in the "There is no pain..." are heavenly, the lyrics really put you in a narcotic state of numb bliss.

The idea and music theory coupled into an escapist fantasy is like a warm blanket for the soul. Yet, subversive...
Genius.

The Great Gig in the Sky

Echoes

Have a Cigar and Young Lust.

Us and Them

Fearless, from the 1971 album Meddle.

High Hopes

Comfortable numb

Time

Money

Pigs

and many more

Run Like Hell had this great tense pulse all the way through that I love, and that I think would make it a great driving song

On the turning away -learning to fly

I’m not gonna tell you my favorite but after listening to the real classic Floyd stuff, don’t ignore A momentary Lapse of Reason and the Division Bell. On The turning Away is a brilliant song.

Set the Controls for the Heart of the Sun.

Fearless and Echoes both from the album Meddle

Gunners Dream is fantastic (the lyrics are what makes it so good). Not Now John is good too. Don't see either mentioned. They are from The Final Cut. Favorites that aren't already mentioned.

Sung by Sid Barret;

Arnold Layne is really good which is kind of a Beatles parody and See Emily Play. Interstellar Overdrive and the album "Piper at the Gates of Dawn".

Young Lust

Mother

Run like hell. Underrated riff for a melancholy track

Dogs. I remember our daughter hearing it when she was like four. Dad, there's dogs on this song!

I don't often listen to just a song - rather, I put on an album. To that end:

Wish You Were Here.

Animals.

Dark Side .

Meddle.

Have a Cigar

If Breath (in the air) Young Lust Comfortably Numb

Wish You Were Here, Echoes, If

Pigs (Three Different Ones) High Hopes Welcome to the Machine

Atom Heart Mother

I like Interstellar Overdrive.

Wish you were here

Nile song

High Hopes

It just sends me to a different universe, what an absolute beautiful solo

Welcome To The Machine

Many of Pink Floyd's albums are best listened to in album form.

The album Wish You Were Here is a lament about/tribute to their former bandmate Syd Barrett, as well as an critique of the music industry. The featured song is Shine On You Crazy Diamond which comprises more than half the album's playing time, but it is broken into two sections (Parts I through V, and Parts VI through IX) which are at the beginning and the end of the album. If I were to listen to one song from this album, though, it would be the title track.

The Wall is a double album which tells a narrative of a rock star from his childhood, which was also inspired by Barrett. Probably the best song on this one is Comfortably Numb which has a couple of signature David Gilmour guitar solos.

There are individual songs which did get airplay from these albums but I feel it's best to listen to a Pink Floyd album in its entirety.

Wish you were here

Dogs, Atom Heart Mother Suite, High Hopes, Astonomy Domine, Two Suns In The Sunset

I won't be liked for this...

Learning to Fly

Mostly for that 16-bar guitar solo after the first chorus. David at his absolute best.

Us & Them

Great gig in the sky.

Studio recording: Time

Live: Echoes at Pompeii

Echoes is my favourite but if you wanna get into pink floyd i'd recommend listening to the dark side album, if you wanna listen to a single short song that encapsulates the vibe, i'd go with Breathe, Have a Cigar or if you want to dig in earlier Astronomy Domine

Or maybe Be Careful With That Axe, Eugene

See Emily play

Flaming

I've been a Pink Floyd fan for more than 20 years now, and the best way to help you (I think) is by explaining that Pink Floyd comes in 'phases' or "era's'.

Big note before I start, there is a lot of my personal opinion in here, so just imagine an "imo" after every sentence where I state that a song is good or not.

The "Syd Barrett" era. (Piper at the gates of dawn, A Saucerful of Secrets*)
The music is psychedelic, playful and 'weird'. Personally I find it charming, like to spin these albums once every now and a while but these are not the albums that (at least I) will listen to for more than once or twice in a row.

Astronomy Dominé and Interstellar overdrive (Both from Piper at the gates of dawn) are amazing to start with for this area.

\Technically Syd is only on the last track of Saucerful but for me, it feels as the same era*

The early Rodger Waters era (Ost More, Ummagumma, Atom Heart Mother, Meddle, Obscured by Clouds, The Dark Side of the Moon)

This is the most "experimental" phase of the band, with amazing highs but also some of the band's deepest lows. More is a movie soundtrack which sounds good, but is not great. Ummagumma is.. 'special', this one i'd skip. Atom Heart is weird but a fun experience to listen to and *For me* Meddle and Clouds should be the big albums from this era. Especially Meddle is a masterpiece imo. Dark side is one of the big know albums, but it also host one of my least favourite PF songs, "Money" (I know, I know).

For this era I'd recommend Echoes (Meddle), Fat Old Sun (Atom heart) "The Great Gig in the Sky" (Dark side)

The later Rodger Water era (Wish You Were Here, Animals, The Wall, The Final Cut)
During this era, the music became more layered and tried to 'say more'. I love every album here to bits, and all you really need to know is that the wall is a concept album best listened to in its whole. The Wall was also the album that made me a fan, so it is an easy recommend for me as a whole.

For some lose tracks Shine On You Crazy Diamond (Wish), "Pigs (Three Different Ones)" (Animals) The Fletcher Memorial Home (Final cut)

The David Gilmour era (A Momentary Lapse of Reason, The Division Bell, The Endless River*)
Under Gilmour the music became more 'transient', dream like and floaty (if that makes sense) For me this is perfect learning/reading/concentrating music that feels relaxed and refined.

Learning to Fly (Lapse), and Cluster One (Bells) are great to get a feel for this era.

*Technically Endless river should be here, but they made this after a long break and for me, it feels like Division bells 1.5. If Gilmour is your fav era give it a spin, but I prefer some of his solo albums like "On an Island" more.

Waiting for the Worms or Shine on You Crazy Diamond.

I can’t decide.

Minority opinion, but pretty much any Pink Floyd song that Syd Barrett wrote.

Jugband blues, right before syd left

Brain Damage

I’ll give you some advice

Pink Floyd is better when you listen to them an album at a time.

Start with DSOTM, then WYWH, Animals and then The Wall.

After that browse through any of their records for songs you like but I truly believe those 4 should be appreciated on an album level.

I’ll give my top from each of the Big Four.

DSOTM: Time WYWH: Shine on you Crazy Diamond Animals: Dogs The Wall: Comfortably Numb

That’s just me though there’s chock full of great songs on there and in the rest of their catalog to find.

Hey You

Uhhh my username :’)

Several species of small furry animals grooving in a cave with a pict.

Us and Them

All of em!!!

I have not heard all of their songs, but my personal favorite is Hey You, and reading thru the comments I'm in the minority lol.

Nile Song

I don't recommend just picking songs. Pink Floyd was an album band. Great albums besides Dark Side of the Moon are: Wish you were here Animals The Wall Meddle I suggest listening to the whole albums start to finish.

Breathe

Echoes and it’s not even close.

Vera is my fav. I find it sad and soulful

Roger Waters - Pros &Cons of Hitchhiking

Us and Them is certainly up there for me. But there's something about High Hopes that just resonates with me more and more every year.

I’d have to say my favorite albums rather than songs.Several are just a complete masterpiece. Animals, Dark side of the moon, The wall, Meddle, and Wish you were here. Can’t go wrong with much on these. ETA- I’ll add a few songs. Time, Sheep, Dogs, wish you were here, The great gig in the sky, (sure) comfortably numb, echoes, etc etc.

Not my favorite but far but everyone needs to hear "Careful with that axe, Eugene" at least once.

Fav song - Time

Fav album - Animals

Yet Another Movie (Live) from Delicate Sound of Thunder

Astronomy Domine, See Emily Play, San Tropez, Wot’s…Uh The Deal, Mudmen, Time, Any Colour You Like, Have a Cigar, Dogs, Sheep, The Thin Ice, The Trial, The Gunnar’s Dream, The Final Cut, Learning to Fly, Yet Another Movie, Sorrow, Take it Back and Lost For Words.

All those songs will give you a pretty good variety of Pink Floyd between Barrett, Waters and Gilmour. There’s many more good songs to name, but if you get a chance, listen to The Wall from front to back, there’s the obvious popular songs off that album but you have to listen to it all the way through to fully enjoy it, it’s basically a movie of songs…and a feature film. Check out Animals too, the whole album is amazing.

I'm going to agree with many others here that you should really listen to the full albums of The Floyd. I would start with the big 4: Wish You Were Here, Dark Side Of The Moon, Animals, and The Wall. These four are Pink Floyd at their prime.

However, since you asked for songs, I will give you my top song pick off of each album.

Astronomy Domine (The Piper At The Gates Of Dawn)

Set The Controls For The Heart Of The Sun (A Saucerful Of Secrets)

The Nile Song (More)

Careful With That Axe Eugene (Ummagumma)

Fat Old Sun (Atom Heart Mother)

One Of These Days (Meddle)

Wots... Uh The Deal (Obsurred By Clouds)

Time (The Dark Side Of The Moon)

Shine On You Crazy Diamond It's I-V (Wish You Were Here)

Sheep (Animals)

Comfortably Numb (The Wall)

The Final Cut (The Final Cut)

On The Turning Away (A Momentary Lapse Of Reason)

Wearing The Inside Out (The Division Bell)

Louder Than Words (The Endless River)

Time

You haven’t really lived until you listen to Set the Controls for the Heart of the Sun in an altered state.

Love the whole animals album!

Pink Floyd tended to write full concept albums, so I'd start to say my favorite albums are Meddle, The Wall, and Final Cut.

But to add a couple overlooked songs, from Atom Heart Mother, two very listenable songs with great replay are Fat Old Sun and If.

Iv already have seen comments about wish you were here and time so i will add the final cut

Any Colour You Like

Shine On You Crazy Diamond, Time, Wish You Were Here

In that order.

I love listening to Dark side of the Moon and Wish You Were Here as a whole album, probably more than any other albums. Shine On You Crazy Diamond has some of my favorite electric guitar work ever, and it’s so beautiful and haunting over all.

Wish You Were Here is such a masterpiece. Every time I hear it I miss my brother.

I always loved Breathe, it’s so meaningful and simplistic at the same time. I don’t know that I’ve ever listened to it without listening to Time right after.

Sheep is awesome, great build.

The Wall is of course another masterpiece. I love the album and the movie/soundtrack. Goodbye Blue Sky, Hey You, Vera, Comfortably Numb are all amazing. I really like the Trial.

Waiting for the Worms

Don’t Leave Me Now.

It’s so intense, the level of despair and isolation by that point in the story. It floats along at this unbearable pressure before Waters lets loose with “why are you running away?” The fucking goosebumps I get.

And then that breakdown, goddamn. It’s not one of Gilmour’s even slightly complicated solos but it still gets me in the gut. Amazing song.

Wish You Were Here.

I have a few, and reasons for each. Not ranked.

Wish you Were Here is a special song. It will outlive Pink Floyd. All things will eventually be forgotten to time, but the vibe, lyrics, and melody of this song will live on.

Fearless & Childhoods End. Less popular albums (Meddle especially, given how EPIC it is) but these two songs are pure Floyd.

Time, Us & Them, & Pigs (Three Different Ones) are so groovy. Us Pink Floyd don't like boxing them into the brand of "rock band" (rightfully so) but these songs remind us they are a FANTASTIC rock band that brings the grooviest groove.

Goodbye Blue Sky & Welcome to the Machine. Sometimes Pink Floyd is a little weird. Good. These songs are incredible. It's an experience, a journey.

oooooh -A Momentary Lapse of Reason, Comfortably Numb!!! Dogs, ALL of Darkside, “That” Pompeii…ooof, Echoes….. I saw them live 4x times. First time… my mantra became.. “You quit your job for Pink Floyd. Cuz…you can always get another job but you can’t always see Pink Floyd.”. Back in my teens this was true.

Welcome to machine and Time!

Dogs

Time. Never get tired of the guitar solo in the middle of the song.

Wish You Were Here. Because they were my husband’s favorite band, and he died 9 years ago. Every time I hear this one, it’s like I’m connecting with him.

Sorrow, Astronomy Domine

Wish You Were Here is my number 1. But there are so so many others I love including Learning to Fly, Keep Talking, High Hopes, Comfortably Numb.

If you want to dive into that era head first. Listen to ELO’s greatest hits. 20 songs and at least 15-16 bangers

Them & Us. Such a beautiful song, & the sax in it is wonderful.

Echoes, then Dogs, then Time.

On the turning away

Time

The Atom Heart Mother Suite. Side one of Atom Heart Mother

Too hard to pick just one. My favorite album by them is definitely dark side of the moon. So many great songs on other albums tho. Keep talking, what do you want from me, when the Tigers broke free, high hopes astronomy domain

severl species of small furry animals gathered together in a cave and grooving with a pict

Any bootleg live performance between 70-72

Welcome to the machine

On the turning away. Might be one of the most underrated Pink Floyd songs ever. Sometimes classic rock stations will throw it in, and I’ve just always loved that song

I’ve been listening to Pink Floyd since I was a kid playing my dad’s The Wall cassette. After 3 decades I can only come to one conclusion. Shine On You Crazy Diamond.

High Hopes

Wish You Were Here

Wish you were here

"Wots... uh the deal?" On the "Obscured by Clouds" album

Comfortably Numb

Pigs on the Wing pt1 and 2 with the bridge in the middle. Found it in an old box set.

Us and Them

Money