You can break down the 15 albums that Pink Floyd made over three decades into several distinct eras. There's the Syd Barrett one, where they were a mind-tripping psychedelic band; there's the post-Barrett era, where they became heady prog-rockers, which gave way to their reign as one of the '70s biggest groups; and finally there's the period after main songwriter Roger Waters left, a mostly indistinguishable decade of by-the-numbers pointlessness. The majority of tracks on our list of the Top 10 Pink Floyd Songs come from that stretch in the '70s when they were one of the hugest bands on the planet. But we left room for some of the trippy stuff too.
'Astronomy Domine'From: 'The Piper at the Gates of Dawn' (1967)
Syd Barrett lasted for only a handful of singles and one album (well, he has one song on Floyd's second LP) before his drug-accelerating mental problems pushed him out of the band. The opening cut on their debut album is an outer-space freak-out that bridges Pink Floyd's psychedelic and prog eras with warped brilliance.
'Have a Cigar'From: 'Wish You Were Here' (1975)
Everyone wanted a piece of Pink Floyd after 'The Dark Side of the Moon' sold a gazillion copies (see No. 6 on our list of the Top 10 Pink Floyd Songs), especially the shady music-industry types Waters never trusted. "Have a Cigar" is all about those clueless suits. "By the way, which one's Pink?" sings guest Roy Harper, a British folkie, summing up the era.
'Brain Damage'From: 'The Dark Side of the Moon' (1973)
The penultimate 'Dark Side of the Moon' track is more or less the theme song of Pink Floyd's most popular album. More than any other cut on the record, "Brain Damage" surveys the mental scars left on both the band and Syd Barrett after their former bandmate's mental illness forced his departure (first from the group and eventually from reality). This centerpiece segues into the closing "Eclipse," so feel free to tack it on.
'Echoes'From: 'Meddle' (1971)
Pink Floyd's sixth album was a turning point of sorts, as the band inched closer to more structured songs, as opposed to the atmospheric set pieces that dominated their previous records. "Echoes," the highlight of 'Meddle,' still runs more than 23 minutes, but its mix of long instrumental passages and vocal patches is a precursor to the career-changing 'The Dark Side of the Moon.'
'Money'From: 'The Dark Side of the Moon' (1973)
Once the band started to receive some attention, the concept of fame and its trappings became an obsession for Waters (see No. 9 on our list of the Top 10 Pink Floyd Songs). Ironically, "Money" – an anti-greed rant – became the group's first hit single and set 'The Dark Side of the Moon' on its path to one of the bestselling albums ever made. Its massive popularity only added to Waters' list of complaints.
'Another Brick in the Wall (Part II)'From: 'The Wall' (1979)
Pink Floyd's only No. 1 single doesn't make a whole lotta sense outside of the hit album's concept, but it's an important song in the band's career and another of songwriter Waters' long list of gripes against society in general. The fact that "Another Brick in the Wall (Part II)" managed to top the pop-music chart says much about the band's popularity in the late '70s and early '80s.
'Shine on You Crazy Diamond'From: 'Wish You Were Here' (1975)
"Shine on You Crazy Diamond" was originally released as a two-song, eight-part, 26-minute suite on the band's follow-up to the mega-popular 'The Dark Side of the Moon.' And like several Floyd projects from the period, the song references former bandmate Syd Barrett's descent into mental illness. It's an epic piece, the bookends to one of the group's most durable LPs.
'Time'From: 'The Dark Side of the Moon' (1973)
Like many tracks on our list of the Top 10 Pink Floyd Songs, "Time" works better as part of a bigger album concept than as a standalone cut. But it's 'The Dark Side of the Moon''s linchpin and features the album's best performances, especially Nick Mason's drum solo near the beginning of the song and David Gilmour's ripping guitar solo in the middle.
'Wish You Were Here'From: 'Wish You Were Here' (1975)
The members of Pink Floyd were still friendly with Syd Barrett after he left the group in 1968. He even showed up in the studio, somewhat unrecognizable, while they were recording of their ninth album. 'The Dark Side of the Moon' touched on the mental illness that crippled Barrett, but 'Wish You Were Here' was an album-length tribute to both his genius and madness. The title track ties Barrett's plight to Waters' own distancing from society.
'Comfortably Numb'From: 'The Wall' (1979)
Waters penned most of 'The Wall' by himself, tracing childhood issues to Floyd-era conflicts. "Comfortably Numb" is one of the few songs written with Gilmour, who supplies the music and terrific guitar solo, one of the most celebrated in rock history. The song shows up in the middle of 'The Wall,' as the main character struggles to get through another day and another show. Then the guitar breaks through the fog, providing a brief glimpse of cathartic clarity.