I know this is over a decade after the original question was asked, but out of the guys still living and who are still working, it's probably hands down these 5 guys: (As of early 2021)
1) Ernie Gutierrez
2) Pete Tascarella
3) Barry Szam
4) Richard Black
5) Dennis Searing
To fill out the top ten, this is subjective, but in my opinion it would probably go down about like this:
Pete Tonkin
Ron Haley
Randy Mobley
James White (JMW)
Joel Hercek
(Note: If Paul Mottey and David Kikel come out of retirement, they would be considered in the latter half of the top 10. David's shaft wood is aged at least 10 years, and his shaft wood turning process takes at least 24 months to turn down a shaft! Consequently his cues are incredibly beautiful, and made with incredible craftsmanship, and they are monster playing cues! And I don't even need to go into why Paul Mottey should be in the top ten)
Rounding out the top 20:
Bill Schick if he's still working (he's getting on up there in age)
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Fred Kohara (Tad cues)
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Tony Scianella (Black Boar cues)
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Paul Drexler (PFD studios)
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SouthWest (With their 15 year wait list, good luck getting one after putting an order in)
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Bob Runde custom cues, the old man hasn't lost his touch since he left Schon, that is for sure!
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Andy Gilbert has probably crept up in the top 20 maybe even as high as top 15, he makes great playing cues
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Chris Nitti
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Bob Manzino
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Richard Chudy (RC3) might be breaching the top 20, even though he pushes the hell out of that CNC (which lacks craftsmanship), but he also has put out some real works of art and his cues play really really good. Go to his website and check out the Stilleto cue, The Sante Fe Collection cue, Winchester cue (the wrap on the Winchester is pure craftmanship), and the British Royalty cue
NOTE: He is the only cue maker that I have named that relies super heavy on the CNC machine. There's always got to be: that one guy
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Alot of names could be thrown out there for strong mention as possible top 20 Mike Vollmer, I've seen some of Dave Barenbrugge is work, and he does some good work. Ed Prewitt and Vigus deserve honorable mention. The Bigglebach's just got in one of Vigus's cues not to long ago, and it's purrrttttty to say the least

. etc... There's some other guys that are getting close that have broke the top 30 and that could possibly get an honorable mention.
Best cues, all around for the money: price to enter, playability, and craftsmanship, probably: Chris Nitti (everything done by hand with magnification optics) and custom work, great craftsmanship (i love his rings), the price is really good, and most of important of all: they are MONSTER playing cues (I have played some very impressive pool with the Nitti I use to own). And probably Andy Gilbert, although the entry price into his cue's is higher these days, he does great work, and boy do they play good (I used to play with a Gilbert Hoppe cue).
Someone else mentioned Rick Horward or Mace cues, and those cues do play phenomenal. I got loaned one to play with one time, and it played really good! But he's not top 20 or 30 that come to mind, but he's close. But for the money,,,,, you get a SouthWest tribute, that's a monster player.
As I said, Kikel didn't mess around as you can tell by the picture below!
