Michael Lindgren is a frequent contributor to The Washington Post.

Paul Simon was never very happy about his appearance. According to Peter Ames Carlin’s biography “Homeward Bound,” as early as 1966 the young singer “became skilled with his comb, developing new and increasingly convoluted patterns to cover the pink top of his otherwise bushy head.” The alchemy of pop stardom is a curious process, and few stories are as unlikely and as absorbing as that of the Jewish kid from Queens turned folk superstar. Fresh off 2012’s “Bruce,” his take on another quintessentially American subject, Carlin provides a brisk and engaging overview of Simon’s career and protean musical output.

The son of a Newark bandleader and a schoolteacher, the young Simon found his way to rock-n-roll via the radio dial, just as many a future star was doing in bedrooms from Liverpool to Los Angeles. A precocious talent, he teamed up with another neighborhood youth named Artie Garfunkel for a short-lived stab at pop stardom, recording the marginal hit “Hey, Schoolgirl” as Tom and Jerry in 1957. When his fling with teen-pop stardom flamed out, Simon decided to forgo performance for a foray into the labyrinthine undercurrents of the record industry as a songwriter and producer.

To my mind, Carlin’s account of this early, near-anonymous phase of Simon’s career is both the most fascinating and the most telling part of the story. Working in the Brill Building, the famed laboratory of the nascent rock industry, Simon found himself alongside other architects of the new sound such as Carole King, Jerry Leiber and Mike Stoller, with “the pickles-and-cigar aura of Tin Pan Alley turning neon with Brylcreem and Tabu, grass-kissed sweatshirts and hairspray.” It was an education in a cheerfully cutthroat approach to songmaking, full of outright theft and bald-faced one-upmanship, built on simulating and repackaging the heat and flash of black music for a white teenage audience. Carlin doesn’t make the point explicit, but the lessons learned in the grimy studios and offices of midcentury Manhattan would shape Simon’s assumptions and methods for the duration of his career.

The fast-and-loose rules of ’60s pop also ended up kick-starting Simon and Garfunkel’s rise into the pop stratosphere. It’s a good story, and Carlin tells it well: In 1964 the duo recorded a lifeless folkie debut album called “Wednesday Morning, 3 AM,” which went nowhere until Columbia Records executive Tom Wilson decided to re-record a bit of portentous minor-key poetry called “The Sound of Silence” with electric instruments and drums, in the style of Bob Dylan and the Byrds. When the record hit, Simon was in England, making a name for himself playing the ultra-earnest folk clubs of London, while Garfunkel was working on his doctoral degree in mathematics at Columbia University. Within a year they were “rock’n’roll’s first intellectual sophisticates,” the ragingly popular “elite practitioners of a new pop art form. . . . Poets. Visionaries. Sages.”

"Homeward Bound: The Life of Paul Simon," by Peter Ames Carlin (Henry Holt)

For the most part “Homeward Bound” is crisp and well-paced, not long on psychological depth or detailed analysis, but generally lucid and evocative. Carlin is especially good when writing about the music, describing Simon’s 1973 classic solo tune “Kodachrome” as “revving the engine with a spinning riff . . . piano jangling, drums kicking, horns blaring.” Not coincidentally, Simon’s work of the mid-1970s, with its sardonic resignation; easy-groovin’ melange of folk, jazz and pop; and inward-focused lyrics marks not just his best work but the period when he was most keenly in tune with the zeitgeist.

Carlin gives a moving description of the famous 1981 reunion concert with Garfunkel in Central Park, when “half a million human beings were made to feel joy on a September evening, all of it so heartfelt and so exactly right that you could forget all about the heartbreaks along the way.”

Carlin is admirably even-handed when faced with Simon’s sometimes acrid personality; the singer’s acts of sudden generosity often “made it seem impossible for such kindness and compassion to exist within the consciousness of the same man,” and one comes to feel that this doubleness, this mixture of the ruthless and the sensitive, is the engine of his entire artistic being. His fractious side surfaces most regularly in his dealings with Garfunkel, who in Carlin’s telling comes across as moody, cerebral and defensive. Chronicling the pair’s half-cen­tury dance of partnership and separation, the central dynamic in both men’s lives, is the first challenge faced by any Simon biographer.

The second, of course, is the fraught, maddening, complex phenomenon that was 1986’s “Graceland” — “this astonishing, troublesome record,” Carlin calls it — which remains the defining achievement of Simon’s career and the apotheosis of both his most brilliant talents and of his darkest, most exploitive instincts. As anyone who was even marginally sentient at the time will recall, Simon’s inescapable hit album was built on rhythms he had recorded in then-apartheid South Africa with a coterie of musicians skilled in indigenous genres such as mbaqanga and famo. The resulting music, as effervescent as it was, raised potent issues about cultural appropriation that remain as trenchant today as they were then.

To understand is not to condone; nonetheless, the primary insight supplied by “Homeward Bound” is in the context of Simon’s long history as a musical and cultural magpie. At some point, Carlin reports, “Paul stopped worrying about how he’d be received by musicians and singers he traveled to work with. They all knew he was a big star and that he paid extremely well for their time and help. If he wanted to project their sound and their names to his enormous audience, how could that be a problem?” This is intentionally disingenuous, of course, and the best Carlin can do in the end is to provide a carefully neutral account of the contretemps, observing mildly that “Paul never cared that much about politics.”

Not surprisingly, the long anticline of Simon’s post-“Graceland” career is the dullest part of the book. A disastrously received foray into musical theater aside, Simon seems to be content to cede the stage to his younger successors, and the author follows him into a stately late-middle-age eminence, not without a slightly smirking description of his looks as “somewhere between a domesticated rock star and a stylishly hip literature professor.” These days, it can be hard to tell the difference.

Homeward Bound
The Life of Paul Simon

By Peter Ames Carlin

Henry Holt. 415 pp. $32