1. "Arnold Layne" 2. "See Emily Play" 3. "Paint Box" 4. "Julia Dream" 5. "Point Me at the Sky" from The Early Singles These songs were recorded during the early years under Barrett, who holds the distinction of naming the band, which is a combination of the names of two blues musicians whose records he owned. The first two songs here were originally included in the band's first full-length album, The Piper at the Gates of Dawn (coming up next in this list), but were later removed because they wanted to stay true to their developing counterculture status. Also controversial were the singles' themes: "Arnold Layne" is about a transvestite (and, according to Waters, based on a real person), and "See Emily Play" is about, well, you'll have to hear it for yourself. I think "Paint Box" is my favorite selection here, not only because of its unusually sublime music a la The Beach Boys' classic Pet Sounds but also because of its instantly identifiable lyrics. The song opens, "Last night, I had too much to drink..." and tells the sorry tale of a poor loser down on his luck with life and the ladies. Later, the narrator laments the bar scene ("Trying to impress, but feeling rather empty/I had another drink") and then uncomfortable first dates ("So what can I do?/I can't think of what to say/She sees through anyway"). "Julia Dream" begins innocently enough but then devolves into an almost nightmarish scenario, with Waters and company hissing threateningly in the background while an ominous organ underscores the drama. And "Point Me at the Sky" soars (quite literally, toward the end) with surreal, out-of-this-world, overlapping melodies set to a twisted fairy tale.
6. "The Scarecrow" 7. "The Gnome" from The Piper at the Gates of Dawn Well, here it is: the band's first studio album. The material is extremely different, even more experimental than their later work when Barrett left the band and Roger Waters took over. "The Scarecrow" is a fun little ditty that would be at home on a children's record or an entry in the diary of a madman. Not many songs can boast that duality; for this reason alone, I included it here. "The Gnome" is also deceptively childish, even beginning like a toddler's picture book ("I want to tell you a story..."), but it's actually a disguised critique of society and our selfish, single-minded ways.
8. "Set the Controls for the Heart of the Sun" from A Saucerful of Secrets In my opinion, this is one of the worst Pink Floyd albums. (This is the one with the aforementioned "Jugband Blues.") This sci-fi gem, however, became a standard at live shows and a favorite with fans. It's one of the first songs that Waters wrote completely on his own, and his writing talent is later capitalized on the hugely successful Dark Side of the Moon, Wish You Were Here, Animals, and, of course, The Wall. Waters' gift lies with inventing original, ironic lyrics, yet surprisingly, this one only features a few lines that are mumbled incoherently, except for the title.