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1* [[https://www.youtube.com/watch?v=FrVwz5al1LE "Positively 4th Street"]] is funny in just how plain BRUTAL it is.
2-->''I wish that for just one time [[InAnotherMansShoes you could stand inside my shoes]]\
3And just for that one moment I could be you\
4Yes, I wish that for just one time you could stand inside my shoes\
5[[TheReasonYouSuckSpeech You'd know what a DRAG it is to see you!]]''
6* Most of ''Music/TheBasementTapes'' songs have some funny turns of phrase ("the comic book and me, just us, we caught the bus."), but a couple can be classified as full-on comedy and are absolutely hilarious: a doo-wop parody called "I'm Your Teenage Prayer" and a bit where Dylan and Music/TheBand [[StylisticSuck deliberately slaughter]] a Mexican ballad.
7** They turn the StylisticSuck up to eleven on the OdeToIntoxication "Bourbon Street". Bob cheers on a painfully bad trombone solo (probably played by Rick Danko): "Play it pretty now, boys! Sounds MARVELOUS!...A ton of joy! I can't take it no more!"
8* On ''The Bootleg Series VI: Live 1964'', recorded just as Dylan was trying to break free of the Protest Singer mold, he is very clearly baked to the gills and in a ''very'' good mood. For instance, his reaction to an audience member requesting "Mary Had A Little Lamb".
9-->[[BigOMG Oh my GOD]]. Did I record ''that''? Is that a ProtestSong?
10** At another point, he tries for a few minutes to get started on "I Don't Believe You" before {{Corpsing}} and [[AudienceParticipation asking the audience how it goes]]. Once somebody sings the opening line, he remembers the rest of the song.
11* The travails of the narrator of "Just Like Tom Thumb's Blues" from ''Music/Highway61Revisited'' get rather amusing, even if you feel sorry for the poor sap. His ScrewThisImOuttaHere reaction to end the song caps off the tour de force.
12** Same goes for "Stuck Inside of Mobile With The Memphis Blues Again", except the situations are more surreal. Don't you hate it when you go to send a letter only to find someone [[StealTheSurroundings stole the post office]]?
13** Same for "On The Road Again". The house he's in doesn't sound very pleasant.
14-->''And you ask why I don't live here - Honey, how come YOU don't MOVE?''
15* '"Motorpsycho Nitemare" is literally a FarmersDaughter joke set to music:
16-->''I fell down to my bended knees\
17Saying, "I dig farmers, don't shoot me please"\
18He cocked his rifle and began to shout\
19"You're that [[TravelingSalesman travelin' salesman]] that I have heard about" \
20I said, "No ! No ! No ! I'm a doctor and it's true\
21I'm a clean-cut kid and I been to college too."''
22* "Foot of Pride", for all its CrapsackWorld-ness, is hysterically funny.
23-->''He looked straight into the sun and said "Revenge is mine!"\
24...But he drinks, and drinks can be fixed.''
25** It also has a great TakeThat aimed at [[CorruptChurch 80s evangelists]]
26-->''Yeah, up on the stage they'll be tryin' to get water out of rocks\
27A whore will pass the hat, collect a hundred grand and say "thanks."\
28They like take all this money from sin, build big universities to study in\
29Sing [[AmazingFreakingGrace "Amazing Grace"]] all the way to the [[SwissBankAccount Swiss banks!]]''
30* "Pay In Blood" has some hilariously cruel lines:
31-->You got the same eyes as your mother does\
32[[MamasBabyPapasMaybe If only you could prove who your father was.]]''
33** and
34-->''I've been through hell, what good did it do?\
35You bastard! I'm supposed to respect '''you'''?''
36* "Brownsville Girl" has some brilliant one-liners:
37-->''She said "Even the swap meets around here are getting pretty corrupt!"''
38** And
39-->''I didn't know whether to duck or to run. So I ran.''
40** And
41-->'''Dylan:''' ''I don’t have any regrets, they can talk about me plenty when I’m gone!''\
42'''Chorus girls:'''[[note]]Including his wife[[/note]] ''Oh YEAH?!''
43* "Highlands" is a 16-minute [[ContemplateOurNavels rumination]] on [[CrapsackWorld mortality, morality and failure...]] in the middle of which, Dylan pops into a diner and gets into a [[FailedAttemptAtDrama bizarre argument]] with the waitress, who thinks he's a famous painter and refuses to let him go until he draws her. The section ends with Dylan running out without paying and returning to his Serious Philosophizing.
44-->''Then she says, “I know [[MistakenIdentity you’re an artist]], [[FanDumb draw a picture of me!]]”\
45I say, “I would if I could, but [[ArtistDisillusionment I don’t do sketches from memory]].”\
46“Well,” she says, “I’m right here in front of you, or haven’t you looked?”\
47I say, “All right, I know, but I don’t have my drawing book!”\
48She gives me a napkin, she says, “You can do it on that”\
49I say, “Yes I could, but [[HurricaneOfExcuses I don’t know where my pencil is at]].”\
50She pulls one out from behind her ear\
51She says, “All right now, go ahead, draw me, I’m standing right here.”\
52I make [[FlatCharacter a few lines]] and I show it for her to see\
53Well, she takes the napkin and throws it back and says, “[[UnpleasableFanbase That don’t look a thing like me!]]”\
54I said, “Oh, kind Miss, it most certainly does.”\
55She says, “You must be jokin’.” I say, “[[StealthInsult I wish I was!]]"''
56* From a 1980 concert:
57-->I want to say hello to Greil Marcus, if he's here tonight. I think he's here tonight. Greil Marcus is one of the...I guess he's the top rock ‘n’ roll critic of the era. [[OverlyNarrowSuperlative Whatever that means]].
58* "Tombstone Blues"
59-->''The sun's not yellow - it's chicken!''
60* "Bob Dylan's 115th Dream". All of it, basically. Dylan tries to discover America, only to find it already occupied by Americans, escapes from jail, keeps losing his clothes, gets mistaken for Music/TheBeatles...
61-->''I ran right through the front door like a hobo sailor does\
62But it was just a funeral parlor and a man asked who I was\
63I repeated that my friends were all in jail, with a sigh\
64He gave me his card and said "Call me if they die!"''
65** Later...
66-->''I decided to flip a coin, like, either heads or tails\
67Would let me know if I should back to ship or back to jail\
68So I hocked my sailor's suit and I got a coin to flip\
69It came up tails, that rhymes with ... [[DirtyCoward sails]], so I made it back to ship''
70* "I Shall Be Free", particularly the last line.
71-->''I make love to Creator/ElizabethTaylor\
72Catch hell from Creator/RichardBurton''
73* In Creator/MartinScorsese's ''Rolling Thunder Revue'', the 78-year-old Dylan trying to explain what the tour was about. And clearly pulling the audience's leg more than once.
74-->'''Dylan:''' I wouldn't say it was a, uh, traditional revue, but it was in the, uh, traditional... um... form of, uh, of a revue. ({{Beat}}, laughs) That's all clumsy bullshit. I'm trying to get to the... To the core of what this Rolling Thunder thing is all about, and I don't have a clue, because it's not... It's about nothing. It's just something that happened 40 years ago. And that's the truth of it. I don't remember a thing about Rolling Thunder. I mean, it happened so long ago I wasn't even ''born'', you know?
75* Many of the improvised duets with Music/JohnnyCash on ''Travelin' Thru'' are chuckle-worthy, but their improvised verses on "Careless Love", trying to one-up each other with increasingly [[PainfulRhyme painful]] rhymes based on gun calibres, is pure comedy.
76-->'''Johnny Cash:''' ''You can pass on by my window pane...'' That don't rhyme with nuthin'!\
77''Pass on by my window pane\
78You can pass on by my window pane, but you can't get by my .44 again!''
79* "Po 'Boy" from ''"Love and Theft"'' includes, of all things, a knock knock joke:
80--> Knockin’ on the door, I say, ‘Who is it and where are you from?’\
81Man says, ‘Freddy!’\
82I say, ‘Freddy who?’\
83He says, ‘Freddy or not here I come!'
84* Dylan is evidently quite fond of cracking [[{{Pun}} dad jokes]] on his Never-Ending Tour. [[https://www.expectingrain.com/jokes.html This page]] collects a number of them up to 2009.

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