Icon: Randy Newman

Released in 1968 (the same year as debut albums from James Taylor and Leonard Cohen), Newman's first LP set the tone for the next 40-plus years of his career, and established him as a singer-songwriter doing something very different from his contemporaries. The record brims with charming little melodies that startle the listener who happens to catch the wicked lyrics – it's funnier than Cohen, more ironic than Taylor and more steeped... in Tin Pan Alley pop than Bob Dylan. The songs tell exquisite little stories. "Love Story," for instance, takes just over three minutes to follow a couple from the time they met to the time they die, but what you remember is the addictive "you and me, babe" refrain. The jaunty "Beehive State" is sung as a conversation between pork-barreling political delegates. "Davy the Fat Boy" witnesses a man turning his tubby friend into a sideshow act, inviting passersby to guess poor Davy's weight: "You've got to let this fat boy in your life!" Newman cries, singing in character, and seducing the listener into a guilty laugh. Cruel? Maybe. But it's such a catchy tune.

Newman's first political album and the ambitious opening bookend of two straight masterpieces, Sail Away opens with the words "In America…," and proceeds to attack that colossal subject from angles rarely found in popular song. (The famous title song, for instance, is sung from the perspective of a slave trader. In a typical Newman twist, the melody is heart-wrenchingly gorgeous.) Meanwhile, "Political Science" packs a cutting, laugh-out-loud-funny colonial satire into just 122... seconds. And "God's Song," a dirge that may be the single best song in Newman's entire catalog, imagines the Lord's deep bemusement – "How we laugh up here in heaven at the prayers you offer me" – at human behavior down on Earth. The litany of classic songs goes on and on: "Lonely At the Top," which would've been a completely different song if Frank Sinatra had sung it, as Newman originally intended; "You Can Leave Your Hat On," the fetish anthem that became a hit for Joe Cocker; "Burn On," an ode to Cleveland's notoriously fire-prone Cuyahoga River. The album's positioned Newman as a major songwriter, and remains a remarkable example of pop music as carefully crafted as literature.

Arguably Newman's strongest album, and certainly one of the definitive creative works about the American South, 1974's Good Old Boys is a meditation on race, politics, marriage, booze and pride. The cast of supporting musicians (Ry Cooder, Don Henley, Glen Frey) is impressive, but no more so than the cast of characters woven throughout these dozen songs. There's Lester Maddox, the racist Georgia governor who appears on a television show in the... opening song, "Rednecks," thus stirring some complicated feelings from a Southerner watching at home, who says "He may be a fool, but he's our fool." There's Huey Long, the populist Louisiana governor who inspired Newman to write "Kingfish," and who actually penned "Every Man A King" (which precedes "Kingfish" on the album). There's Marie, the jilted lover, whose drunk husband is too much of a bum to treat her right, and knows it. There's a textile machinist and a naked man, a black dog whose name is Dan, and "a Polish girl with a space between her teeth." These people and more stumble and brag their way through Newman's world, which comes to life in piano-driven songs that might be called "chamber pop" if that didn't suggest something so precious. Yes, there are strings. And yes, the music is carefully composed. But this is no soft-focus nostalgia trip or condescending head-pat to America's backwater. It's an empathetic, but not uncritical look at the kind of people who endure a great flood ("Louisiana 1927") and assume someone's out for revenge. That the song resurfaced as a Hurricane Katrina anthem serves to prove just how us-versus-them the South can still be – and how right Newman got the place the first time around.

With punk, disco and prog-rock swirling in the air, it's little wonder that Newman's 1979 album sits awkwardly in his pantheon. Always a square peg in a round hole, Newman was especially out of place at this moment in music history. Still, it's difficult to imagine him getting angry enough at Electric Light Orchestra to write a song ("Story of a Rock & Roll Band") that gleefully mocks the "Mr. Blue Sky"... rockers in both style and lyric. And for that matter, what's up with the KISS makeup on the cover? While those references feel dated now, "It's Money That I Love" stayed relevant through Gordon Gekko and Occupy Wall Street. And in keeping with Newman's knack for romantic misadventure, the album gives us "You Just Got Married" (a kind of sequel to "Love Story," from Newman's first album) and "The Girls In My Life, Pt. 1" (which bemoans a woman who borrowed the narrator's car, and then plowed over a man in Mexico).

While no one would confuse Trouble in Paradise with a serious concept record like Dark Side of the Moon (or, for that matter, Newman's own Good Old Boys) the album still comes off as a postcard from the go-go 1980s. Never before or since did Newman write so much about quintessential rock 'n' roll subjects like sunshine and girls. "There's A Party At My House" feels like such big, dumb fun that... it's almost out of character – and then Newman cracks a joke about bondage. The cheerful and half-joking "I Love L.A.," which kicks off the record, would become a kind of theme song for the singer, and rightfully so – it's a perfect mix of genuine affection and faux ignorance, and it comes paired with a similar (if lesser) song called "Miami" for everybody back East. Anyone bothered by the cheesy, deeply '80s production style can turn for relief to "Real Emotional Girl," a ballad performed with just voice and piano.

Perhaps the most underrated album in the career of an underrated artist, Land of Dreams captures Newman in a charming mood. (Okay, there's a vicious ballad called "I Want You To Hurt Like I Do" – it's still a Randy Newman record – but most of its memorable songs are easygoing larks.) Four stand out: "Dixie Flyer" and "New Orleans Wins The War" are utterly delightful nostalgia trips about Newman's beloved birthplace;... "Falling In Love" has an addictive seven-note hook that can hover in your head all day; and "Something Special" is a Newman rarity – an unabashedly happy love song. Together these highlights constitute an extremely strong batch, highly recommended as a second step after the essentials of Sail Away and Good Old Boys.

At this point, the musical production Faust (like Cop Rock, the ill-fated, Newman-scored TV musical about singing law-enforcement officers) remains pretty unheralded. Any career this long is going to have its footnotes and pitfalls, and maybe this is Newman's. And yet, even here amid an album that's tough to play all the way through, there are songs worth plucking. For instance "Glory Train" is a lovely bit of call-and-response gospel voiced largely... by James Taylor. (Other guests on the project include Ry Cooder, Bonnie Raitt and Elton John.) And almost as good is the spry "I Gotta Be Your Man," which bops along with a nervous high-hat rhythm and a careening piano line that dips and swerves like a roller coaster.

Although Toy Story is arguably the most famous of Newman's countless original film scores, and although it contains the instant-classic buddy anthem "You've Got A Friend In Me," the album still couldn't quite break Newman's famous bridesmaid's streak at the Academy Awards. (He wouldn't win until his 16th Oscar nomination, for Monsters Inc., in 2001). In any event, the album – which is largely instrumental compositions – stands as an approachable entry... point for parents looking to introduce children to orchestral music. And it also contains another pop song (the wistful "I Will Go Sailing No More") that ranks among the most beautiful tunes Newman has ever written.

By this point in his career, Newman had already released his most famous material. He was no longer a young man, no longer the Next Dylan, or for that matter, the next anything. He was just himself. And so Bad Love may come off as more of the same — more witty piano-pop about sex, death and regret, with a dash of political imperialism for good measure — and how you feel... about that may depend on whether you've been on the bandwagon all along. In any case, as usual, the songs aren't all depressing, as the subject matter might lend you to believe. This is Newman, after all, who treats his unsympathetic narrators (in this case, the guy who sings the sugar-daddy's lament "Shame") with mercy, and who cares enough to play at least a few of his ballads (like "I Miss You" and "Every Time It Rains") straight. Fans of "Political Science" can get their dose of social commentary on "The Great Nations of Europe" and "The World Isn't Fair" (which cheekily describes Karl Marx as "a public-spirited man"). But unlike some of Newman's previous offerings, Bad Love is less about individual songs and more of an album — consistent, and not his best, but a respectable continuation of the themes he's dealt with all along.

After almost a decade releasing film scores instead of pop songs, Newman returns with an album that could be said to show his age (after all, it's about lost love, mortality and parenting), except that those subjects have been in his wheelhouse all along. In fact, the album feels quintessentially Newman-esque, with "A Few Words in Defense of Our Country" playing like the third song in a trilogy with "Political Science" and... "The Great Nations of Europe." "Korean Parents," meanwhile, is a biting Tiger Mother send-up, and the sunny "Laugh and Be Happy" is so blithe that you think Newman, the irony king, can't possibly be serious. But the real standout is the title track – a droll tale of one man's brief visit to the afterlife, with a melody and a lyric that could've been written by anyone else.