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Spoiler

I love upside down puzzles, too.

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Jimmy gathers up his cylindrical possessions and then persuades the Dame of Dangerous Disproportion to help him liberate Larry from the Vendito machine.  They heave with all their strength, but can only budge Larry a couple of inches.

Care Bears!

Is he/she/it employed (for money)?

Jimmy unties the now overstretched latex stocking and then humbly asks the Dame of Dangerous Disproportion for forgiveness, and for help extracting his friend Larry, and for any spare change she might be carrying.  Meanwhile the vending machine finally stops churning, coming to rest with one box of Llama brand cigarettes and two cans of Garlic Cola.  Larry's cries now fade to whimpers.

[John Madden offers to deflate iffy balls' in 'Penhagen.]

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I've got nothing concrete.  The letters seem to start words, although why there would be two apostrophes in that case beats me.  But the "in'P" bit makes me think P might be a place, maybe starting with a syllable that is usually dropped.  So my guess is  John Madden offers to deflate iffy balls' in 'Penhagen.   (Grammatically I don't know why his iffy balls would be possessive... )

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Correctamundo el stupido!

NEXT!

It is Panthro!   

Next!

But... room 2A has no doorknob! 

Your cunning plan fails.

I'd like to confirm this guess but ...what guess?

Some thoughts:

Spoiler

I'm thinking "blind guy from Miami" means something like "no eyes" so to take the i's out of Miami leaving "mam". That leaves 4 letters to describe "stinky" and the only word I could come up with was "rank" but couldn't fit them together in any useful way...

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Yeah, you're on the right track.  But...

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a guy from Miami is not called "Miami".

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The rotating dials on the El Vendito machine begin to stop, while Jimmy attempts to aid his stricken comrade.  Unfortunately, with each tug poor Larry's arm seems to get more and more stuck!

One week left, folks.  Keep those mysteries pouring in!

Well, I think it was just a little unfair to keep us guessing when the correct answer had already been guessed, but I appreciate your reasoning.

Stinky, blind guy from Miami (7)

Spoiler

AGS Related

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Jimmy returns the shoe to the Dame of Dangerous Disproportions and then, while she's distracted, he uses the antique casino chip in the vending machine and pulls the crank arm.  The contents of the vending machine begin spinning!  Meanwhile Larry begins squealing about Mary Mother of God (perhaps he has smelled the presence of a pregnant Jewish teenager?).  In the ensuing chaos the cockroach makes good its escape.

[Bop It?]

All right....

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"Out of their Prime" numbers are 1, 4, 6, 8, 9, 10, 12, 14, 15, 16, 18, 20, 21, 22.... I'm not going to continue the list beyond the word count in the clue, because I'm still assuming the sequence of the words themselves is important.  Scanning the clue for new meaning I see that "not first" probably means not using the first non-Prime number, so don't use 1.  From the beginning of the clue we therefore have in slots 4, 6, 8, 9, 10 words be, of, prime, if, they, or b o p i t.  Er... Bop It? 

I'm still troubled by not using the last 12 words of the clue or so.  It seems ...wasteful.  There must be something I'm not seeing....  Let's try something different: looking at the clue meticulously I see that by letter count there are exactly five words that don't have a prime amount of letters.  They are:

Any (3) man (3) could (5) be (2) out (3) of (2) their (5) prime (5) if (2) they (4) did (3) not (3) first (5) accept (6) the (3) lack (4) of (2) energy (6) which (5) saturates (9) their (5) being (5)

Interestingly the first letter of each word with a non-prime word count listed sequentially is t a l e s, which also happens to be a GIP by AprilSkies.  So I'm guessing Tales again, only this time for different reasons.

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Jimmy tries to make a grab for the wallpaper but is foiled by the Dame of Dangerous Disproportions who now accuses him of stealing her shoe.  He counters suavely with a foolproof Cinderella pick-up line, distracting DDD long enough for Larry to slip past and try his hand at the vending machine.  While the distracted Dame of Dangerous Disproportions is still dumbstruck, Jimmy quickly offers her assistance with her vending machine woes.  This softens the slap-the-creepy-guy look she was trying on for size, and for a moment she seems to be considering it.

[Since there are so few letters in the answer are we looking for initial letters of five words maybe?]

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Ok, Ok, Ok.  So from CaptainD with Mandle's hints we have....

Any man = Male?  Out of their prime = Old?  Since there are so few letters in the answer are we looking for initial letters of five words maybe?  "if they did not first accept" = the order of the letters in the word perhaps?

And now through MiteWiseacreLives! we know it has something to do with prime numbers. 

So... just going out on a limb here, but would it be an anagram of the initial letters of the prime numbered words?

Let's see....  Prime numbers are 2, 3, 5, 7, 11, 13, 17.... but we probably only need the first five.

Any man could be out of their prime if they did not first accept the lack of energy which saturates their being. (5)

The first letters of the prime words are... M, C, O, T, D.  So.... M^cDot?

But.... wait, why would the clue be so long?  Why would the word "first" be unused in a cryptic crossword clue?  It must be part of the clue!  It's the thirteenth word, so....  13, 17, 19, 23 -blast!  There are only 22 words in the clue.  That would give us F, O, W.... another dead end.  Maybe "lack of energy" means you start rolling back down the hill you just climbed, so you  are supposed to go backwards from "First" (13), so F, D, T, O, C -no, that still doesn't work.  Gah!  Taking non-prime numbers starting at "first" (13) gives us A, T, L, E, S -these are much more promising letters.  So the answer could be slate, stale, steal, least or ....tales?

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[Any man could be out of their prime if they did not first accept the lack of energy which saturates their being. (5)]

Any man could be out of their prime if they did not first accept the lack of energy which saturates their being. (5) 

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It's like a plot arc: first accept, energy which, prime if, lack of, out of = awioo!

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After determining that each other's trousers smell acceptably, Larry and Jimmy proceed to the vending machine.  There they meet a Dame of Dangerous Disproportions who is attempting to assault the vending machine.  Jimmy attempts to circumvent her fury and insert the antique poker chip into the machine's coin slot, but ends up kicked in the face.  Perhaps a more artful approach is required?