what songs would you recommend to a new listener?
It’s difficult to recommend individual songs because all except Pink Floyd’s earliest work is based on albums rather than singles, but here is one path you could follow:
Start with The Dark Side of the Moon (1973). The essential songs are Time, Money, Us & Them, and Brain Damage / Eclipse, but the whole album is recommended.
Next, Wish You Were Here (1975). The key tracks are Shine On You Crazy Diamond and the title track, but again it’s best to listen to the whole album. The album is a tribute to founding member Syd Barrett and has a theme of absence as well as makes a statement about what the music industry can do to a person. I think it’s also important to understand the historical context: Dark Side of the Moon was wildly successful, and Wish You Were Here is the album that followed it.
From here, we go to The Wall (1979). Essential tracks are Another Brick in the Wall Part 2, Young Lust, Hey You, Comfortably Numb, and Run Like Hell. The album is a rock opera and the context of each of these songs is lost unless you listen to the whole album.
So far you may not have heard anything that a classic rock radio station does not play, but now it’s time to explore the songs that they don’t play. There are big differences in musical and lyrical styles between Wish You Were Here and The Wall. The bridge between them is Animals (1977). The album is loosely based on George Orwell’s Animal Farm. It is overlooked by radio because the three principal songs are each 10+ minute jams. In my opinion, Animals and especially the song Dogs is some of Pink Floyd’s best work.
Moving backwards from DSOTM, the album Meddle (1971) has One of These Days and the 23 minute epic Echoes, a masterpiece of psychedelic rock and a turning point for the band that led them to DSOTM. If you want to hear how they arrived at Echoes, there’s Astronomy Domine and Interstellar Overdrive from The Piper at the Gates of Dawn (1967), and Set the Controls for the Heart of the Sun and the title track from A Saucerful of Secrets (1968). And if you can’t get enough of Floyd’s psychedelic period then Atom Heart Mother (1970) is for you.
If you love The Wall and the political commentary of Animals, there is The Final Cut (1983) which is Roger Waters’ last album with the Floyd. On this album, Richard Wright is completely absent (having been fired during The Wall sessions), and David Gilmour has little input other than some guitar solos (if you listen closely you can hear his frustration). The album is essentially a Roger Waters solo work. It is Waters’ political statement on Margaret Thatcher’s England, provoked by the Falklands war in 1982. It is the least accessible to casual fans, but by this point you are probably no longer a casual fan.
A Momentary Lapse of Reason (1987) and The Division Bell (1994) are the Floyd albums of the post-Waters era. Learning to Fly, On the Turning Away, Sorrow, What Do You Want From Me, Keep Talking, and High Hopes are the highlights of those. Sorrow is one of my favorites, the guitar solo is in my opinion Gilmour’s best work since Comfortably Numb.
The 1972 film Pink Floyd: Live at Pompeii features excellent live performances of Echoes, A Saucerful of Secrets, Set the Controls for the Heart of the Sun, One of These Days, and Careful with That Axe, Eugene.
From there you’re going into solo territory with the albums of Roger Waters, David Gilmour, and Richard Wright, as well as the leftover albums in the psychedelic period such as Ummagumma, Obscured by Clouds, and the More soundtrack.