Songs, in three passes

Song	Where it lives	Why it matters
Comfortably Numb	The Wall, 1979	Two verses of numbness, one guitar solo of pure feeling. Gilmour's masterpiece moment.
Wish You Were Here	Wish You Were Here, 1975	An acoustic campfire song about absence — missing Syd, missing sincerity, missing whoever is not in the room.
Another Brick in the Wall, Pt. 2	The Wall, 1979	The disco-beat protest single with the Islington school choir. Their only UK number one.
Money	The Dark Side of the Moon, 1973	Seven-beat loop of clinking cash from Waters' girlfriend's coin collection, turned into a hit about how money rots people.
Time	The Dark Side of the Moon, 1973	A wall of ringing clocks, then the most quietly terrifying verse they ever wrote: "then one day you find ten years have got behind you."
Shine On You Crazy Diamond (Pts. I–V)	Wish You Were Here, 1975	Nine minutes of grief for Syd, played in a tuning that shouldn't work and does.

Song	Where it lives	Why it matters
Echoes	Meddle, 1971	Twenty-three minutes: pings, wind, seagulls from a Binson Echorec, and the best melody they never released as a single.
Breathe (In the Air)	Dark Side, 1973	The album's gentlest two and a half minutes, and its thesis statement.
Dogs	Animals, 1977	Seventeen minutes of corporate wolves. Gilmour's guitar chases its own tail on purpose.
The Great Gig in the Sky	Dark Side, 1973	Richard Wright's chord sequence and Clare Torry's voice as the sound of dying. No words needed.
Us and Them	Dark Side, 1973	War, generals, and the saxophone of Dick Parry. The saddest chord progression in their catalog.

Song	Where it lives	Why it matters
Fearless	Meddle, 1971	Gilmour's warmest slide work over a field recording of Liverpool fans singing You'll Never Walk Alone.
Wots… Uh the Deal	Obscured by Clouds, 1972	A lost single-never-was: gentle, wistful, better than half of the famous records.
If	Atom Heart Mother, 1970	Waters alone with a guitar, before he decided tenderness was a weakness.
Fat Old Sun	Atom Heart Mother, 1970	Gilmour's English-summer reverie, best in the extended live versions.
When the Tigers Broke Free	The Wall film, 1982 / Echoes compilation, 2001	Waters' song about his father's death at Anzio — outside the album for two decades, essential to the story.
High Hopes	The Division Bell, 1994	The elegy for Cambridge: bells, zeppelins over the meadows, and the last song on the last album.

“I don’t think I’m a great songwriter, but I think I’m a good one. What I do well is the long form: building an album so the songs need each other.” — the case for listening to whole records, not playlists