500 Greatest Albums

100. In the Wee Small Hours – Frank Sinatra

In the Wee Small Hours, the first collection of songs Sinatra recorded specifically for an LP, sustains a midnight mood of loneliness and lost love ”” it’s a prototypical concept album. From the title track, brought in on the bell tones of a celesta, through a trenchant recast of “This Love of Mine,” a hit from his Tommy Dorsey days, Sinatra ”” reeling from his breakup with Ava Gardner ”” is never less than superb. His voice rarely hits the same downbeat as his languorous rhythm section, yet they’re locked in a fluid step. Put your ear close to the speaker and you can hear the soft intake of his breath.

99. There’s A Riot Going On – Sly and the Family Stone

This highly anticipated studio follow-up to Sly and the Family Stone’s 1969 blast of hope, Stand!, was the grim, exact opposite: implosive, numbing, darkly self-referential. Sly Stone’s voice is an exhausted grumble; the funk in “Family Affair,” “Runnin’ Away” and especially the closing downward spiral, “Thank You for Talkin’ to Me Africa,” is spare and bleak, fiercely compelling in its anguish over the unfulfilled promises of civil rights and hippie counterculture. “It is Muzak with its finger on the trigger,” wrote critic Greil Marcus in Mystery Train. Take that as a recommendation.

98. This Year’s Model – Elvis Costello

His second album and first with his crack backing band the Attractions, This Year’s Model is the most “punk” of Costello’s records ”” not in any I-hate-the-cops sense but in his emotionally explosive writing (“No Action,” “Lipstick Vogue,” “Pump It Up”) and the Attractions’ vicious gallop (particularly the psycho-circus organ playing of Steve Nieve). Many of the songs rattle with sexual paranoia, but the broadside against vanilla-pop broadcasting, “Radio, Radio” (a U.K. single added to the original U.S. vinyl LP), better reflects the general, righteous indignation of the album: Costello vs. the world. And Costello wins.

97. The Freewheelin’ Bob Dylan – Bob Dylan

Dylan’s second LP was released on May 27th, 1963 ”” three days after his twenty-second birthday. It was a tender age for such a historic triumph. On Freewheelin’, the poetry and articulate fury of Dylan’s lyrics and his simple, compelling melodies transformed American popular songwriting. He later made light of the protest anthem “Blowing in the Wind” (“I wrote that in ten minutes,” he said in ’66). But Dylan’s wholly original grip on grit, truth and beauty in “A Hard Rain’s A-Gonna Fall” and “Masters of War” still changes everyone who hears this album, four decades later.

96. Tommy – The Who

“Rock Opera” is one way to describe the pioneering ambition in Pete Townshend’s musical exploration of childhood trauma, sexual abuse, repression and spiritual release. Here’s another way: the slash and thunder of “My Generation” blown wide open. Driven by the hellbent drumming of Keith Moon, the Who surge and shine, igniting the drama in Townshend’s melodies (“Pinball Wizard,” “We’re Not Gonna Take It”). “We worked out the sociological implications, the religious implications, the rock implications,” he said. “When we’d done that, we went into the studio, got smashed out of our brains and made it.”

95. Green River – Creedence Clearwater Revival

The third Creedence Clearwater Revival album was their first classic LP, a tightly wrapped package of blistering guitar, roadhouse-rhythm snap and John Fogerty’s backwoods howl. The lengthy jamming on CCR’s previous LPs is gone, and Fogerty has found his lyrical voice ”” radio-ready essays in frontier living (“Green River,” “Lodi”) and working-stiff politics (“Bad Moon Rising,” “Wrote a Song for Everyone”). As producer, he makes it all sound so gritty and easy, too ”” like CCR had cut it all in a toolshed. “All this overproduction is funny to me,” Fogerty has said. “It doesn’t make it mo’ betta when you add more junk.”

94. Bitches Brew – Miles Davis

In February 1969, Davis recorded In a Silent Way, a bold step into ambient funk and electric futurism that inspired the trumpeter to go further out at the sessions for Bitches Brew that August. Davis wanted, he said, “the best damn rock & roll band in the world,” to connect jazz with the forward motion of Jimi Hendrix and Sly Stone. Davis’ band was superbad (Joe Zawinul, John McLaughlin, Chick Corea, Wayne Shorter, etc.). But the word fusion was never big enough to describe the visceral thrill of these explosive studio explorations and the pioneering tape-edit wizardry of producer Teo Macero, arguably the original Chemical Brother.

93. Sign ‘o’ the Times – Prince

He’d fired his band, and his latest movie had flopped; just three years after Purple Rain, Prince was in the market for a comeback. So he recorded one of the great albums of the Eighties. Times is best known for the apocalyptic title track, the brontosaurus funk of “Housequake” and the gorgeous “If I Was Your Girlfriend.” Yet the simplest moments are unforgettable: the “Sweet Jane”-style guitar plea of “The Cross,” the Stax revamp on “Slow Love,” a jilted girl’s sadness in “I Could Never Take the Place of Your Man.” “I hate the word experiment,” Prince said. “It sounds like something you didn’t finish.” Here, he finished.

92. 20 Golden Greats – Buddy Holly

Holly spent his teenage years kicking around Texas playing straight country music ”” until, at nineteen, he got a gig opening for Elvis Presley. With that, Holly later claimed, he became a rock & roller. For the next two years, he put his trademark vocal hiccup on springy rockabilly, orchestral ballads and Chuck Berry covers ”” an eclecticism that had a huge impact on the future Beatles. “Rave On,” “Peggy Sue” and “Not Fade Away” made Holly one of rock’s first great singer-songwriters. He was also its first major casualty: dead at twenty-two, in a plane crash after a show in Iowa in 1959. He was just getting started.

91. Goodbye Yellow Brick Road – Elton John

When John compared himself to the Beatles, it wasn’t just a delusion of grandeur. “Revolver lifted them onto a higher plane, and Honky Chateau did the same for us,” he said in 1973. “Then they did the White Album, and now we’ll have a double, too.” Everything about Goodbye Yellow Brick Road is supersonically huge, from the Wagnerian-opera-like combo of “Funeral for a Friend” and “Love Lies Bleeding” to the electric boots and mohair suit of “Bennie and the Jets.” On the title track, John and his songwriting partner, Bernie Taupin, harnessed the fantastical imagery of glam to a Gershwin-sweet melody.