The album is named after a 1993 study of black minstrelsy by Virginia social historian Eric Lott, Love and Theft: Blackface Minstrelsy and the American Working Class. However, Love and Theft is only tangentially about popular exploitation of black culture. Not surprisingly the album's jaunty style was reminiscent of the live shows leading up to Love and Theft, in which Dylan covered numerous songs pre-dating rock 'n' roll and re-arranged his older material with country and blues styles that also pre-dated rock 'n' roll.

"Love and Theft becomes his Fables of the Reconstruction, to borrow an R.E.M. album title," writes Greg Kot in The Chicago Tribune (published Sep. 11, 2001), "the myths, mysteries and folklore of the South as a backdrop for one of the finest roots-rock albums ever made."

The opening track, "'Tweedle Dee & Tweedle Dum,' rolls in like a storm, drums galloping over the horizon into ear shot, guitar riffs slicing with terse dexterity while a tale about a pair of vagabonds unfolds," writes Kot . "It ends in death, and sets the stage for an album populated by rogues, con men, outcasts, gamblers, gunfighters and desperados, many of them with nothing to lose, some of them out of their minds, all of them quintessentially American.

"They're the kind of twisted, instantly memorable characters one meets in John Ford's westerns, Jack Kerouc's road novels, but, most of all, in the blues and country songs of the 1920s, '30s and '40s. This is a tour of American music -- jump blues, slow blues, rockabilly, Tin Pan Alley ballads, country swing -- that evokes the sprawl, fatalism and subversive humor of Dylan's sacred text, Harry Smith's Anthology of American Folk Music, the pre-rock voicings of Hank Williams, Charley Patton and Johnnie Ray, among others, and the ultradry humor of Groucho Marx."

Unlike the other songs, the album's second track, "Mississippi" was originally recorded for Time Out of Mind in 1997, but it was omitted from that album. Sheryl Crow would later record it for The Globe Sessions, released in 1998, before Dylan revisited it for Love and Theft.

"In the deceptively rollicking 'Summer Days,' a case of the wedding-day blues ends with the narrator high-tailing it out of town, but not before he sets 'fire to the place,'" writes Kot. An upbeat, fast-tempo number propelled by its swinging momentum, the arrangement recalls a number of jump blues recordings from the immediate post-WWII era.

The following track is also performed with a retro arrangement, bearing a strong resemblance to small group, jazz recordings recorded in the 1930's and 1940's. "Obsession turns to murder in the lounge-crooner ballad 'Bye Bye,'" writes Kot, "as Dylan ominously declares, 'You were my first love, and you will be my last.'"

As Tim Riley of NPR notes, "[Dylan's] singing [on Love and Theft] shifts artfully between humble and ironic...'I'm not quite as cool or forgiving as I sound,' he sings in 'Floater,' which is either hilarious or horrifying, and probably a little of both."

"Love and Theft is, as the title implies, a kind of homage," writes Kot, "[and] never more so than on 'High Water (for Charley Patton),' in which Dylan draws a sweeping portrait of the South's racial history, with the unsung blues singer as a symbol of the region's cultural richness and ingrained social cruelties. Rumbling drums and moaning backing vocals suggest that things are going from bad to worse. 'It's tough out there,' Dylan rasps. 'High water everywhere.' Death and dementia shadow the album, tempered by tenderness and wicked gallow's humor."

"'Po Boy,' scored for banjo with lounge chord jazz patterns, 'almost sounds as if it could have been recorded around 1920," says Riley. "He leaves you dangling at the end of each bridge, lets the band punctuate the trail of words he's squeezed into his lines, which gives it a reluctant soft-shoe charm."

The album closes with "Sugar Baby," a lengthy, dirge-like ballad, noted for its evocative, apocalyptic imagery and sparse production drenched in echo. Praising it as "a finale to be proud of," Riley notes that "Sugar Baby" is "built on a disarmingly simple riff that turns foreboding."

Christopher Ricks, a Warren Professor of the Humanities, writes extensively on "Sugar Baby" in his book, Dylan's Visions of Sin. "The song's beat is fourfold, and the rhythm of the instrumental opening is immediately confirmed by there being four syllables in each of the first two units. But the words that provide the title and that later open the refrain, 'Sugar Baby,' have their four syllables two by two, 2 x 2. The rhythm of the words 'Sugar Baby' is a dual rhythm, fourfold and twofold. And in pacing the song, Dylan pauses at certain points so as to make two syllables occupy the time and space that in the basic scheme of things will be expected to be occupied by four syllables. It is this movement in the voicing, with its pauses (contemplative, disconcerted, riven, chary, sardonic, shifting its grounds), that gives to the song its unique gait..." The song also bears the influence of Gene Austin's "Lonesome Road," first copyrighted in 1928; "Sugar Baby" even quotes a line from Austin's song: "Look up, look up and seek your Maker, 'fore Gabriel blows his horn." However, while both songs share a feeling of apocalyptic dread, the phrasing and structure is very different. "At every point in ['Lonesome Road'], the words and the music and the voice are fittingly in place," Ricks writes. "In ['Sugar Baby'], they are at odds. They move as the spirit takes them, and their spirit engages not only with the precious but with the precarious."