“Now I know what you’re thinkin’.” “Barry and Levon, where did you get two hundred and forty dollars?” “Shhhhhhh.” “Don’t worry your pretty little head about it, baby.” 
Ding ding ding! 
About the $240 worth of pudding: that was . . . weird.
Still awaiting answers:
S3: $38.82
S6: “Here’s a dime.” (Actual dialogue; I’m anticipating a particular incorrect guess)
And I’ll add another:
S7: “FOUR dollars?” (Hint: this one comes from the same movie as another clue already mentioned, and the movie was a wrong guess for a different clue.)
want2know: Would a bit of dialogue help with your clues, or give them away?
Might give them away…
Tell you what, change “dollar” to “buck” on W1.
And W2 (movie) and W3 (TV) both take place outside the US.
Oh, heck, make that in the UK.
Anyone? Anyone? Jésus?
Did you notice Barry was Thomas Lennon, aka the short-shorted Lieutenant Dangle from Reno 911? Levon was Michael Ian Black, the current host of “Reality Bites Back.”
These three are hardish, so I’ll give a hint: they’re all movies with a common theme.
pr3: $570 - $20 for the job, $50 for the date, $500 for expenses
pr4: $250, just this once, then you retire
pr5: $1000 reward for a hairpiece, dead or alive
R1 - $300, $400, $500.
Goldfinger?
Nope. See #44 for a hint.
Thought of another one, used by two different charaters.
LS2: $200 a day, plus expenses.
I started to put that one up myself. Jim Rockford on “The Rockford Files” was one, I think Magnum PI was the other.
Right on both.
Three Kings
New one:
X2: $30,000,000
I don’t recall anyone referred to as “Jésus” in that movie.
Incorrect. The answer the judges were looking for was “Die Hard With A Vengence” - the amount the terrorists carried in their pockets to pay for the tolls.
John Houseman to Timothy Bottoms in The Paper Chase. The full line (paraphrased) is, “Mr. Hart, here’s a dime. Call your mother and tell her you’re leaving law school.”
Team America. It’s a heavy fuckin’ fee.
Cool, another duplicate! Again, I had another movie in mind. Here’s another one from the same movie:
$85 a month (it used to be $80)
Here’s the full line for the dime reference:
“Just making a personal call. Here’s a dime.”
From the same movie: “I know the man, I know the family. The only thing better than blowing up a hundred billion dollars worth of gold bullion is making everyone think you did.”
Fuckin’ A right!
OK, more hints:
W2: Unlike the above, the answer is “very clean”.
W3: If you don’t know this one, “you’re a weedy pigeon, and you can call me Susan if it isn’t so!”
pr3: $570 - $20 for the job, $50 for the date, $500 for expenses
I’m going to take a guess with “10 things I hate about you”?
pr5: $1000 reward for a hairpiece, dead or alive
Wallace & Grommit’s Curse of the Were Rabbit??? Nah, that can’t be it…