The Jamies, Summertime, Summertime.
The Jamies were a quartet from the Boston neighborhood of Dorchester (one of the guys has a honker of an accent): siblings Tom and Serena Jameson, Jeannie Ray and Arthur Blair. "Summertime, Summertime" was their one-hit wonder. Has any song better captured the joy of the first day after school's ended, with nothing but an endless length of sun-blessed days stretching out before you?
I love the glorious ramshackle nature of this track--the way everyone singing seems on the verge of going flat, or the zinging harpsichord, which sounds like the Jamies' dotty great-aunt is accompanying them, or the way Serena has to cram in an overlong line (so it sounds like "cos whatsa sum'vacation without romance" and you can hear her stumble midway through, poor kid).
There's one line that's always puzzled me: "It's time to head straight for the mills." As a kid, when first hearing this song, I thought of a bunch of teenagers being shipped off to work at a textile factory or something, which seemed a cruel betrayal of the song's philosophy. But what are they singing? The most common, quite logical theory has it that the Jamies are actually singing "It's time to head straight for them hills." The dark horse theory, however, ventured by one crank on Usenet back in the day, was that the Jamies were singing about heading for "The Mills"--a reference to "Dorchester Mills," an alleged hot beach spot somewhere in the Boston area. The main flaw with this theory is that I've never run across any other reference to the so-called "Dorchester Mills" in my life.
(Boston anecdote: I once saw some kids, maybe 10 or 11 years old, walking along Commonwealth Avenue, near Kenmore Square. They were a bit rough, like a 1990 version of the Dead End Kids. One of them hurled a huge plastic Coke cup on the sidewalk behind him. His friend, seeing this, yelled at him: "Hey, this isn't Dorchester!")
While "Summertime" was initially released as Epic 9281 in September 1958 (how cruel to put this track out just as school was resuming), it was reissued four years later. On 25 All-Time Greatest Summer Songs.