"September Gurls" (Big Star)

Although Alex Chilton was just 16 years old when he recorded the #1 hit "The Letter" (1967) with the Memphis-based band The Box Tops, his gritty, bluesy voice sounded like that of someone three times his age.  Chilton would score one more Top 10 hit with The Box Tops (1968's "Cry Like A Baby") before the group decided to call it quits in 1970.
From there, Chilton joined up with former schoolmate and songwriter/guitarist Chris Bell, an adamant Anglophile and Beatles fanatic, to found the band Big Star.  Chilton permanently retired his affected blue-eyed soul growl and began finding his true voice through their Lennon-McCartney-esque songwriting partnership, which generated some of the best so-called "power pop" ever recorded. 
Story goes, Big Star (which also consisted of bassist Andy Hummel and drummer Jody Stephens) recorded its debut album #1 Record in mid-1971 and released it to a huge amount of critical fanfare in early 1972.  But despite the praise and expectations of making it big (it was called #1 Record, after all), the album simply didn't sell.  
The problem was not that the music didn't resonate; it was record label politics.
Big Star's label—the indie outfit Ardent Records, a subsidiary of the Memphis R&B/soul label Stax Records—had worked out a distribution deal through Columbia Records, where music mogul and all-around douchebag Clive Davis was head of operations in the early 70s.  Davis got canned after getting caught with his hand in the company coffers, and the new guard at Columbia saw the distribution arrangement with Stax/Ardent as a threat to its own record sales.  So they essentially let #1 Record and other Stax/Ardent recordings wither on the vine by simply not shipping their albums to record stores.  
In turn, #1 Record sold fewer than 10,000 copies, and Stax went bankrupt.
After the album flopped, Bell departed the band and spent time hanging out in Europe, where he attempted to cut a solo record.  In the meantime, Chilton went back into the studio in Memphis and cut a second album called Radio City (1974)—which, incidentally, sounds more like late-70s Television, mid-80s R.E.M., or 2000's Wilco than anything Big Star's contemporaries were producing, circa 1974.  The album is filled with instantly catchy melodies that have beautifully jagged edges and unexpected twists, as well as smart lyrics, real emotion, and unbridled, uncompromising creativity.  It was way ahead of its time and still sounds amazingly fresh.  
(Unfortunately, it also met with poor sales and led to the band's disintegration before its brilliantly quirky third album, Sister Lovers, was released.)
A standout song from Radio City is "September Gurls"—a Chilton-penned song that's about longing and depression and sex and girls and loneliness...all in three terse stanzas and two perfect minutes and forty-eight immaculate seconds.  The track has the same kind of chiming guitar sound as a Byrds or Beatles track from 1965/66 with the same kind of spry immediacy and urgency, too.  Chilton's vocals (including his harmony backing vocals) sound as sunny and bright as a day at the beach yet are tinged with real melancholy, adding a layer of complexity to what might have been just a fluffy pop confection in lesser hands.
A classic song from a classic album.