Bob Dylan, strictly speaking, is pop. He was pop by the definitions of pop music holding sway in the mid to late Sixties when the word became associated with experimentation, the avant-guard. "Pop" and "Rock" were interchangeable terms. Peter Townsend was the one who coined the term "power pop", in an interview I read in the old Hit Parader music journal, and used the phrase to describe the Who. It was a term he used to define the Beach Boys, a band he admired quite a bit Definitions of terms change, of course, and with the re-emergence of conspicuously commercial tunes in a post-punk era came a new pop music that was heavy on irony and purely obsessed with its hook value.
The Beach Boys were an extension of the harmony prone Four Freshmen, a vocal style overlaid upon a Chuck Berry chord progression with lyrics addressing concerns not of the 40s or 50s, surfing and souped cars. The who borrowed the Beach Boys' vocalese and used it in conjunction with a musical style premised on power chords and snarling teen hooliganism. Dylan, though, was the one who broke from the pack, taking his inspiration from the nominally "pure" genres contained in the folk music revival. The good man, though, had something larger to do rather than adhere to principles; fame was his goal, and fortune; he walked backward into genius, into the backwoods with this nasal, grunting vocals and lyrics that blended an idealized proletariat idiom with great heaping doses of Verlaine and Eliot: he brought literary Modernism to the jukebox. He also understood the dynamics of being a teen ideal. If he couldn't be sexy/dangerous like Elvis, he could at least be vague, mysterious, "poetic".
The "dignity" and" integrity" that Dylan refused to be marginalized by--ie, made quaint and neutered as a revolutionary force of any definition--were those notions codified by the lefty Folk Revival he eventually abandoned. Their idea of those qualities had little to do with Polonius's greatest platitude--"...to thine own self-be true..." --and everything to do with conformity to a vaguely held consensus. I would only insist that the means of Dylan following his muse amounts to deftly selected instances of opportunism. Had Dylan been less inspired in his mashing together of his unlike influences, we likely would have regarded him as a pretentious fool trying to beserk himself into genius. Dylan, though, was a genius, and his careerism is mitigated in the music and lyrics that resulted from it. The work is everything. It took rock and roll by surprise. Someone like Dylan from the Sixties wouldn't be considered pop at all. He had singles that found chart positions, he earned gold albums, he toured internationally, gave interviews and signed autographs. He was a pop star, a pop artist, a contradiction that refused to be marginalized by unprofitable consolations such as dignity or integrity. He was going to be famous and get rich; he was a pop star and a punk. Our punk, our genius.