English majors and their willful ignorance of basic microeconomics! I doubt you could even buy a vowel for FIVE DOLLARs these days, much less a fancy-pants word. I wonder what five dollars bought back when this term was coined. Probably a manse, a horse and buggy, and you'd still get a bag of gold dust in return.

Reminds me of when my just-out-of-school brother-in-law had a delicious meal and a cold beer and said, "I feel like a hundred bucks!" Chris could have bought twenty juicy words that night.
It's a shame that the term isn't FOUR DOLLAR WORDS, since NOTE, BUCK, BILL, and CLAM all fit so tidily into single squares (if you write carefully). Not so much with SINGLE. Jamming six letters into a SINGLE square is bonkers, which is why Will Shortz almost always sticks to shorter rebus words.
As an embarrassingly bad bridge player, SINGLETON came easily to me. I'm not sure how common that term is outside the bridge world, but then again, if you don't play bridge, you're of no consequence.
I appreciate when rebus squares are worked into both long across and long down entries. It'd be easier to do the bare minimum with shorties like (BILL)ED or (NOTE)LL, so I enjoyed the pairings of ICE (BUCK)ET CHALLENGE and BUCKAROO, as well as HORN(BILL) and (BILL) MAHER.
(NOTE)LL … I usually love rebuses where the word is disguised this well. It stuck out today, though, since the rest of the rebuses read as individual words, or at least identifiable syllables.
With so many long rebus entries—many of which crossed each other — it wasn't surprising to get a logjam of BOR DEG ELAM (I finished with an error, ELAH / NO TELL HOTEL) ETO, etc. If I had five dollars for every dab of crossword glue …
I'd have preferred a scaled-back version, perhaps with a simpler DOLLAR revealer and four rebuses (no SINGLE), since the term FIVE DOLLAR WORDS didn't do anything for me. Still, I can appreciate the audacity of the concept.