Given Randy Newman's love of the sardonic, it probably makes him chuckle that for all his aspirations and gifts, he will always be known as the curmudgeon who made fun of folks of diminutive stature and the composer of scores for Pixar cartoons. When it comes to those animated fairy tales, Newman's facility for composing film music—he's been nominated for 22 Academy Awards in music and won twice—is simply a matter of carrying on the family business. He's the nephew of a trio of composer-conductor uncles: Emil; Lionel; and Alfred, who scored over 200 films and was nominated for an incredible 45 Academy Awards in music categories, winning nine times. Newman's scores for films like Toy Story, A Bug's Life, and Monsters, Inc. have made him Pixar's go-to music brain. His skills at cinematic orchestrations and arrangements also superpower his solo career. While the soundtracks have earned him wide acclaim, his parallel singer-songwriter career is the sweet underbelly of his legacy. Endlessly cannibalizing his own songs with impeccable songcraft, he has come up with more than a few memorable melodies. And then there's his laser eye for detail. Newman's solo work is populated with flawed but very human characters who serve as vessels for his expansive intelligence, corrosive cynicism, extreme social conscience, and outright comedy. His laconic, Southern-accented delivery, bespectacled persona, and matter-of-fact descriptive powers all make universalities out of his compassion, humor, and venom. So much so that his distinctive musical style earned him a hilarious guest appearance on an episode of the animated TV series Family Guy. What follows is a many-hued sampling of Newman's kaleidoscopic film and solo careers.

"Mama Told Me Not To Come" from 12 Songs (1970, Reprise)

Leaving his customary lush string orchestrations behind for 12 Songs, Newman enlisted a small group of SoCal rock heavyweights, including drummer Jim Gordon and guitarists Clarence White and Ry Cooder, who add a country rock feel to this amusing tale of an anxious newbie who's aghast at a Hollywood party and thinks back on some warning advice from his mama: "that ain't the way to have fun ... son." While Three Dog Night made this into a #1 hit in 1970, it has since been covered by acts as diverse as Tom Jones and Yo La Tengo. This version is the most tentative and anxious of all, however, settling in the minds of many that a nerdy personality must go with Newman's glasses, talky delivery, and brainy smirk.

"Sail Away" from Sail Away (1972, Reprise)

Despite his playfulness and love of happy, even wonderfully silly songs, this is where Newman's playing and songwriting gifts first turned toward a more serious subject that's become a lifelong passion: fighting racism. Having spent part of his childhood in New Orleans, he was aware of the South's long history with African Americans. Here he sings from the POV of a slaver trying to entice potential slaves by talking up the joys of America where "every man is free and the easy life doesn't have "no lion or tiger, ain't no mamba snake/ just the sweet watermelon and the buckwheat cake." Taken at a slow, stately tempo, this is also where Newman's orchestrations of horns and strings first ascend to a new level of sensitivity and taste.

"Birmingham" and "Louisiana 1927" from Good Old Boys (1974, Reprise)

This penultimate volume in his collection of insights about the American South is also the pinnacle of Newman's solo career—the man at the very peak of his melodic and intellectual powers. Although the subjects and details come from his experiences in Louisiana, this is world-class chamber pop with cinematic sweep, featuring his finest arrangements for horns and strings. If there is any downside it's that the songs are too short—all seeming to need at least one more verse! In "Birmingham," Newman inhabits the character of a steelworker whose father was "a most unsightly man," and whose dog is gleefully "the meanest dog in Alabam'/Get 'em Dan!" The portrait here, while gently poking fun, is ultimately sympathetic, which will not always be the case in Newman's songbook. Based on the trials and tribulations caused by the Great Mississippi Flood of 1927, Newman's sturdy melody in "Louisiana 1927" has become an unofficial anthem of the state. Forever influenced by Professor Longhair and other New Orleans keyboard giants, his playing is a sterling example of being your own best accompanist. The song is filled with savory details like calling then President Calvin Coolidge "A little fat man with a notepad in his hand." The majestic use of an orchestra-sized backing band is superb throughout. This album spaned Newman as a cut above, an uncommonly crafty and talented songwriter who dreamed big and had the musical dexterity to realize his ambitions.

"The Blues" from Trouble in Paradise (1983, Warner Bros.)

Not unlike the career arc of Jackson Browne, there was a time in the mid-1980s when Newman shifted gears and tried on a shiny production style complete with electric keyboards and female backup singers, while attempting to bill himself as a hip, overproduced SoCal singer/songwriter. While there were moments like "Song for the Dead" where his intelligence was too bright even for all the gloss to disguise, this was also the era of "Short People" and Newman's widest success as a solo artist, so being less clever was kind of the point. Here he trades verses with Paul Simon on a detailed, deadpan tale of a faux white bluesman who, unlike the genuine practitioners of this form, has no real problems to sing about. As is so often the case, the tempo and arrangement are exactly right.

"Dixie Flyer" from Land of Dreams (1988, Reprise)

One striking aspect about Newman's solo work is that while he's expert at creating hilarious, despicable, or sympathetic characters, he rarely speaks directly about himself. Although fictionalized around the edges—the real Dixie Flyer ran from Chicago to Florida—Newman writes in his favored ragtime/New Orleans piano professor–mode about his mother "Dixie" fleeing Los Angeles for her hometown of New Orleans on the train. Aware now of the discrimination he encountered as a Jewish child in the South, he creates a memorable scene when the train pulls into New Orleans:

Her brothers and her sisters came down from Jackson, Mississippi

In a great green Hudson driven by a Gentile they knew

Drinkin' rye whiskey from a flask in the back seat

Tryin' to do like the Gentiles do

Christ, they wanted to be Gentiles, too

Who wouldn't down there, wouldn't you?

An American Christian, God damn.

While the giddy, tuneful "Falling in Love" and the acerbic "It's Money That Matters span this album produced by heavyweights Jeff Lynne, Mark Knopfler, James Newton Howard, and Tommy LiPuma as a strong post-'70s set, the opening trio of "Dixie Flyer, "New Orleans Wins the War," and "Four Eyes"—all straight out of Newman's biography—make this a rare personal statement. This time the character he's painting in detail is himself.