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My goofy old Kay - TRAGIC. Hockey, anyone?
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I'm a "form follows function" guy. For that reason, I will always prefer an angled headstock to a straight one. Aesthetics do play a secondary role, however, which is why I much prefer the Tobias headstock over the Warwick.
Criteria for a good headstock:
- Angled design (none of that string tree nonsense)
- Straight (or nearly straight) string pull through the nut
- Symmetry near the nut (for aesthetics as well as hanging straight on the wall)
- Compact (saves weight)
- No obvious vulnerabilities (pointy bits)
- No all-inline tuners (purely an aesthetic choice)
- Compact and lightweight tuners
For this reason, the Tobias headstock is a thing of beauty.
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The Warmoth house-style headstock is nice too, though the 4-string is not symmetrical near the nut.
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The classic Gibson EB-0/Les Paul design, while pleasingly symmetrical, fails the "straight string pull" criterion in a big way, a shortcoming it shares with many high-end manufacturers.
The classic Fender designs, whether Jazz/Pre or Tele, fail on almost every count. The original Tele design is one of the ugliest things I've ever seen this side of a Wishbass.
I hate angled headstocks. It's not the natural shape of the wood, which means it's prone to being weaker. How many times have you seen a Gibson headstock snap off? How many times have you seen a Fender headstock snap off? Yeah.
I've never seen an Alembic headstock I thought looked good.
(Epic) Fail:
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the body is an equally over-sized slab of excess ballast.

Win:
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(Epic) Fail:
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+1
To me it says "I'm Gumby, Dammit"
)Criteria for a good headstock:
- Angled design (none of that string tree nonsense)
- Straight (or nearly straight) string pull through the nut
- Symmetry near the nut (for aesthetics as well as hanging straight on the wall)
- Compact (saves weight)
- No obvious vulnerabilities (pointy bits)
- No all-inline tuners (purely an aesthetic choice)
- Compact and lightweight tuners
Actually, I've seen several broken Fender headstocks. Anything made of wood can break if sufficiently abused.
Gibson's overpriced vanity junk breaks because it's overweight, poorly designed, lacks a volute, and uses inappropriate materials for the job, not because they use a tilt-back.
How many broken Tobias headstocks have you seen?