What I want is to take a filled rectangle and punch a hole in it using another shape. This is exactly the kind of thing that NSBezierPath is designed for. You add a rectangular path, then add the subpath that will "punch" through it and finally fill it. In my case the subpath is actually text. No problem, works great:

Except when I use Helvetica Neue Bold for my font. When I use that, I just end up with a solid blue rectangle without any text at all. But the subpath is indeed drawing--in fact, if I shrink the filled rectangle a bit, you can actually see some of the text path:

I get the same behavior with Helvetica Neue Italic. Helvetica Neue Medium works fine, as does Helvetica Bold, Times New Roman Bold and Arial Bold.
I've tried using both NSEvenOddWindingRule and NSNonZeroWindingRule. (EDIT: Apparently I didn't really try NSEvenOddWinding rule, because that does turn out to work after all)
This is the code that I'm using inside the drawRect method of my NSView subclass.
NSLayoutManager *layoutManger = [[[NSLayoutManager alloc] init] autorelease];
NSTextContainer *textContainer = [[[NSTextContainer alloc]
initWithContainerSize:NSMakeSize(300, 100)] autorelease];
NSFont *font = [NSFont fontWithName:@"Helvetica Neue Bold" size:100];
NSDictionary *textAttribs = [NSDictionary dictionaryWithObjectsAndKeys:
font, NSFontAttributeName, nil];
NSTextStorage *textStorage = [[[NSTextStorage alloc] initWithString:@"Hello"
attributes:textAttribs] autorelease];
[layoutManger addTextContainer:textContainer];
[layoutManger setTextStorage:textStorage];
NSRange glyphRange = [layoutManger glyphRangeForTextContainer:textContainer];