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* BlackSheepHit: "Lay Lady Lay" is a very popular song and one of Dylan's biggest hits, but it's a country ballad sung in a crooning style that is definitely not in Dylan's typical style.
* BreakawayPopHit: "Knockin' on Heaven's Door" from ''Film/PatGarrettAndBillyTheKid''.
* BreakthroughHit: "Blowin' in the Wind". Technically speaking, it wasn't his version to be his first hit - it did not even chart, but it was a hit when covered by Peter, Paul and Mary. That said, it's the song that made him indeed internationally popular and is still one of his absolute {{Signature Song}}s.
** If you go by charting songs, the classic "The Times They Are A-Changin'" was his first hit in the UK, while "Like a Rolling Stone" (arguably also his SignatureSong) was his first hit in the US. "Subterranean Homesick Blues" was his first charting single in the US, but it just barely scraped into the Top 40 (though, very bizarrely, it made the Top 10 on the Easy Listening chart).
* BuryYourArt: Dylan's 1978 concert film/experimental drama hybrid ''Renaldo and Clara'' (documenting the Rolling Thunder Revue tour) has been suppressed following its critical and commercial failure, having been out of circulation since 1980 save for a handful of European TV broadcasts (which has allowed fans to KeepCirculatingTheTapes). With Dylan and Creator/MartinScorsese revisiting the same tour and concept with 2019's ''Rolling Thunder Revue'' film to greater success, ''Renaldo and Clara'' is unlikely to see the light of day any time soon.
* ChartDisplacement: On one hand, his biggest hit is also his possible signature, as "Like a Rolling Stone" reached #2. On the other, this means the classic songs released prior to it barely charted, including "The Times They Are A-Changin'" (a top 10 hit in the UK nonetheless), "Blowin' in the Wind" (which missed the US charts altogether, overshadowed by the Music/PeterPaulAndMary version), "Mr. Tambourine Man" (not even released as a single), and "Subterranean Homesick Blues" (a mere #39).
* CreatorBacklash:
** Dylan pretty much wrote his debut album out of canon, simply put, with a bunch of the songs only performed a small handful of times live.
** Dylan has apologized for "Ballad in Plain D", a one-sided document of the disintegration of his relationship with Suze Rotolo. He was quoted in 1985 as saying "I look back at that particular one and say, of all the songs I've written, maybe I could have left that alone." Rotolo claimed she never felt hurt by the song, and said that she understood that Dylan was channeling his emotions into his music. Her sister Carla, on the other hand, quite understandably never forgave Dylan for calling her a "parasite" in the lyrics which also accused her of sabotaging the relationship. One critic compared listening to the song to reading someone else's private mail.
** The panned movie ''Hearts of Fire'', which he starred in. He's done everything possible to keep it unmentioned in his official biographies. Even his official song database omits one of the songs he did for the film and the other two are listed without mentioning the soundtrack.
** PlayedWith in the case of his hit song "Lay Lady Lay". While he doesn't necessarily ''hate'' the song, some sources report that he's not a fan of it either and describes the song as being [[BlackSheepHit definitely not representative of his music style]].
* CreatorPreferredAdaptation: He loved Music/JimiHendrix's version of "All Along the Watchtower" and has often said that it improved on his own version. Following Hendrix's death Dylan started to perform the song in Hendrix's style as a tribute.
* CreatorRecovery:
** After his 1966 motorcycle accident he settled into married life and fatherhood, and his next few albums featured a less [[WordSaladLyrics Word Salad-ish]] lyrical style, musical RevisitingTheRoots (back to folk and country), and quite a few SillyLoveSongs.
** Averted with his albums after his Christian conversion. If anything his lyrics became more strident.
* CreatorsFavoriteEpisode:
** He's often cited ''Music/BlondeOnBlonde'' as the album he's most proud of, with his description of it as "thin, wild mercury music" in a 1978 ''Magazine/RollingStone'' interview being almost a mandatory quote in anything written about it.
** Judging from his latter-day concert setlists, he also holds ''Music/Highway61Revisited'' in high regard--"Tombstone Blues" (last played in 2006) and "From a Buick 6" (only played twice in 1965) are the only songs he hasn't played live in the last decade.
** He's also been quoted a few times as having affection for the much less celebrated ''Shot of Love'' from 1981
* FanCommunityNickname: Bobcats, though some fans feel like it's a ForcedMeme.
* HitlessHitAlbum: ''Music/JohnWesleyHarding'', ''Music/SelfPortrait'', ''Music/NewMorning'', ''Music/PlanetWaves'', ''Music/TimeOutOfMind'', ''"Love and Theft"'', ''Modern Times'', ''Together Through Life'', ''Tempest'' and ''Rough and Rowdy Ways'' all made the Top Ten in the US without a Top 40 hit single.
* KeepCirculatingTheTapes: To the extent where the 1969 release ''[[http://en.wikipedia.org/wiki/Great_White_Wonder Great White Wonder]]'' is considered the TropeCodifier for unauthorized bootleg albums. Dylan was also (along with Music/FrankZappa) among the first artists to acknowledge the demand for unreleased music by releasing official versions of songs that had been bootlegged for years. Still, even with eighteen (and counting) volumes of the official ''Bootleg Series'', there are still scores of unreleased songs, one out-of-print album (''Dylan'') and literally [[ArchivePanic thousands of live recordings]].
* MeaningfulReleaseDate: ''Tempest'' hitting the streets on September 11, 2012 was seemingly a nod to ''"Love and Theft"'' having infamously been released on 9/11/01. Coincidentally, ''Under the Red Sky'' was also issued on September 11 (way back in 1990, though).
* ReclusiveArtist: While he still plays nearly 100 concerts a year, he rarely does interviews[[note]]And when he does it's usually with journalists who have interviewed him before and he seems to trust, like Bill Flanagan and Edna Gundersen.[[/note]] and is known for keeping his recording sessions top secret, only announcing new albums on short notice before they're released. He's played out the more literal version of this trope from time-to-time as well, taking breaks from his work.
* TrollingCreator: Arguably one of this trope's main [[TropeCodifier codifiers]].
* WhatCouldHaveBeen:
** There was talk of Dylan recording an album backed by Music/TheByrds in 1969, which made sense since they shared a label (Creator/ColumbiaRecords) and a producer (Bob Johnston). But Dylan seemed to lose interest in the idea quickly, and The Byrds fired Johnston after just one album.
** Dylan and Music/TheBand spent much of the summer of 1967 in the basement of their house, fooling around with covers and original songs, and recording snippets of it on an old tape machine. ''Music/TheBasementTapes'', as released 8 years later, contains only a handful of the songs recorded, often with obvious overdubs, and padded with Music/TheBand originals recorded years later. A lot of fans agree that some of the songs left off are among his best ever - or at least would have been if they'd been finished. It took until 2014 and the release of vol 11 of the Bootleg Series for most of the songs to see daylight.
** Similarly, from 1974 (''Music/BloodOnTheTracks'') onward, Dylan has frequently second-guessed his studio performances, leaving off songs or performances from his studio albums that fans, critics, producers and backup musicians consider far better than what ended up on the album. Some of the more obvious examples include "Blind Willie [=McTell=]", "Mississippi", "Caribbean Wind", "Abandoned Love" and "Series of Dreams". A lot of these have since ended up on the various ''Bootleg Series'' releases.
** He was asked to play at the Film/MontereyPop Festival, but he was still recovering from his motorcycle accident the previous year. Music/JimiHendrix paid tribute to him by covering "Like a Rolling Stone".
** Could Dylan have played {{Film/Woodstock}} in 1969? The organizers asked him, expecting he'd say no, and while he seemed negative about the idea (mainly fearing for his safety) he didn't formally say no. A few days before the festival he told an associate that he was still considering it. He was ultimately a no-show, but two weeks later appeared at Woodstock's TransAtlanticEquivalent on The Isle of Wight, suggesting that money may have been the issue all along. He ''did'' play Woodstock '94 and the Bethel Woods Center for the Arts on the original site in 2000s (with jokey stage banter implying that he'd played there in '69 after all).
*** Woodstock's location was chosen ''because'' it was near where Dylan was living at the time. When Dylan returned from Europe, he was angry about hippies lingering around his house days after the festival had been completed.
** He was reportedly Creator/WarrenBeatty's first choice to play Clyde Barrow in ''Film/BonnieAndClyde'' before Beatty decided to star as well as produce. Dylan recently confirmed this but suggested that Albert Grossman didn't pass along the offer to him because they were on poor terms at the time. There's still a Dylan presence in the final film: Michael J. Pollard based C.W. Moss' voice on Dylan's.
** In March 1984, Dylan appeared on ''Series/LateNight with Creator/DavidLetterman'' backed by the L.A. post-punk band the Plugz for a three-song set considered one of Dylan's best-ever television performances and a highlight of a decade where Dylan was largely written off. The performance was so popular with his fans that it even circulated as a bootleg recording for years. However, Dylan never followed up on either his chemistry with the Plugz nor the acclaim his stylistic shift received. The Letterman set is often thought of as a great "what-if" moment in rock history, to the point where the Canadian indie band Daniel Romano's Outfit released full-length cover of Dylan's 1983 album ''Infidels'' in 2020 done in the post-punk style of the Plugz and titled it ''Daniel Romano's Outfit Do (What Could Have Been) Infidels By Bob Dylan & the Plugz''.
** The Bob Dylan Center has some notebooks in which Dylan jotted down some ideas while he was editing his experimental documentary ''Eat the Document'', and buried among them is a very intriguing entry: the name and home address of Creator/AlfredHitchcock. Whether Dylan was somehow going to try to enlist Hitchcock's help in putting ''Eat the Document'' together, or the two were considering a different potential collaboration, is not known.
* WorkingTitle: ''Music/BlondeOnBlonde'' boasts such classic tunes as "A Long-Haired Mule and a Porcupine Here", "What You Can Do For Your Wigwam" and "Seems Like a Freeze-Out"...or, as they ended up becoming, "Rainy Day Women #12 & 35", "Pledging My Time" and "Visions of Johanna".
** ''Music/PlanetWaves'' was originally going to be called ''Love Songs'', then ''Ceremonies of The Horseman'' (a CallBack to "Love Minus Zero/No Limit" from ''Music/BringingItAllBackHome'').
* WritingByTheSeatOfYourPants: He's gone both ways with this when it comes to songwriting. For many of his albums he arrived at the studio with the songs already written in advance. For ''Music/BlondeOnBlonde'' he wrote a good deal of it in the studio, leaving the musicians to jam or play cards while they waited ("Sad-Eyed Lady of the Lowlands" was recorded with the ink still drying on the lyrics). ''Music/NashvilleSkyline'' was also largely written during the recording sessions.
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