There are plenty of Modern Art threads on the SDMB - perhaps search on “Rothko” or the user capybara, whom I haven’t seen lately but is an expert and patient with the Modern Art is all Crap types.
I’m having a brain fart moment as to exactly what acts/shows/movies qualify, but I have to think that a lot of comedy straddles this particular edge.
Good point, I nominate Zoolander as a film that is both stupid and clever.
Oh yeah!
Bill and Ted’s Excellent Adventure
Something like Buckaroo Banzai, too!
Toby Keith himself described “Red Solo Cup” as “the stupidest thing I’ve ever written”, but I think it’s pretty damned clever 
Yeah, I was thinking of Buckaroo, wondering if it was appropriate for this thread.
I really loved this movie. I recently re-watched it with my son. Yet I don’t really know if it’s genius, or stupid, or both.
The cheesiness of the production values and dialog contrasts with the caliber of the actors in a very interesting way. The weirdest part is how seriously the movie takes itself. It certainly has many layers. But also, the plot is actually a bit lame and the dialog is often wooden and expository.
For me, I think the big thrill is imagining a world where there could be a Buckaroo Banzai person, a comic book character in real life. (That’s why I love lines like- hunter looks at comic book with his flashlight and says, “It’s ‘Buckaroo Banzai’; it’s the latest issue.”)
I’m guessing the actors either had a blast making that movie, or hated every minute.
Laugh a-while you can Monkey Boy!!
So many great, stupid lines in that movie.
Oh lord, Buckaroo Banzai is probably the poster child for this idea, if anything is. It’s dialogue is littered with priceless jewels that make you wonder if there actually is a line, or if you can only accurately graph clever/stupid with the overlap of a Venn diagram
Dr. Lizardo: Laugh(a) while you can, monkeyboy!
The President: Buckaroo, I don’t know what to say. Lectroids? Planet 10? Nuclear extortion? A girl named “John”?
And again, the Prez.: What are you talking about, man? Some kind of race war in New Jersey?
Buckaroo Banzai: John Parker, take this wheel. Just… just hold on, that’s good. It flies like a truck.
John Parker: Good. {pause} What is a truck?
Buckaroo Banzai: {as the thermopod is in free-fall} Can’t you fly this thing?
John Parker: I’m a diplomat! I failed flight school!
New Jersey: Why is there a watermelon there?
Reno Nevada: {after a pause} I’ll tell you later.
Scooter Lindley (who is about 10 years old): Get away from that car, or I’ll drink your blood!
Secretary of Defense: {noticing Scooter is holding an automatic rifle}Whatcha got there, son? That’s not… real, is it?
Scooter Lindley: {fires a shot to the side} Get 'em up!
ETA: Hahah! I actually say that to people IRL. 
Overhead PA: “There are monkey-boys in the facility.”
Billboard: “Yoyodyne- Where the Future Begins Tomorrow!”
Gotta love’em. I could go on and on.
They really had me when I bought the line about the promised sequel- I now believe it was a joke and they had no intention to deliver.
Clearly, there was completed sequel for Buckaroo Banzai vs. the World Crime League, but somehow it fell into nefarious hands! 
It must’ve been that she-devil, HRC! Lock her up!
I laughed like a loon at this. Thanks, man. 
Huh? I honestly can’t grasp what point you’re trying to make. Your first link is Lay Lady Lay from 1969, when he had already sold tons of records with his “blues singer” voice as you put it. One of his biggest single hits btw. Second link, The Time They Are-A Changing, is from 1964. Heck, Dylan sounded never more like a blues man than on his very first album. Even if you unintentionally swapped the links, it wouldn’t make sense. He DID change his voice for 1969’s Nashville Skyline, nobody knows exactly why (he said it was caused by having stopped smoking. Right Bob ;)), but I’ve never heard anything about him trying to sound more commercial. This voice was in any way a brief intermezzo (and one of the many oddities) in his career that was forgotten after the next album, Self Portrait.
This is probably my favorite Dylan verse of all, and I bet the napkin theory is much more probable, or maybe he wrote it in the back of the studio between two takes. That was his style of writing in those times. And right, later he employed the other method, in fact he had long spells of writer’s block later in his career, whereas he could write a song in ten minutes in the mid-sixties. For me, everything in those lines makes sense (except for “No Doz” because I don’t know what it means) and it gives me glimpses of the time and place in which it was written. Of course WordMan is right, the flow and the beat in those lines are crucial, that’s why they work better when Dylan sings them than printed on paper or pixels on a screen, respectively.
“No Doz” = caffeine pills IIRC.
Stone Age “Red Bull”
Ah, I’ve got one: for a while here on the SDMB, I have posted to Best Lyric-type threads with this. Also, there’s been a recent, kerfuffly Beatles Suck thread where “you show me your best Beatles lyric and I will show you better!!!” was tossed down all gauntlet-y (and shit). If it would’ve been productive, I would’ve posted it again there.
The Beatles, When I Saw Her Standing There: "She was just seventeen, you know what I mean."
Paul thought it was stupid. He trotted it out as filler while he was trying to sell the song to John.
John knew it was clever. Because, yeah, we knew exactly what Paul meant. He told Paul “no way, keep it in!!”
Fuckin’ A. I love that.
Bingo! I totally “get” Pollock. I did from the very first canvas I saw. Rothko, I just don’t “get”.
I don’t actually think he’s saying “No Doz”. I admit that I was lazy and grabbed the lyrics from the intertubes. Should have been more careful. I can’t tell with certainty from the record, but after some further research, I think the actual line is:
FWIW, this bugged me, so I checked my good old print copy of the official “Lyrics 1962-1985“, and there it is “Don’t try ‘No Doz’“. Although this is an official publication, it’s somehow infamous for sloppy transliteration and so there is no guarantee for accuracy, but this is how I also always heard it, without knowing the meaning until this thread.
I swear I’m hearing “no bows”. Maybe I’m going nuts, though.
Yet another possibility: In the famous video, Bob is holding up a cue card at that point with the text “no dose”. Some of those cards are punny, though, so it doesn’t have to mean anything.