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Any suggestions? I searched FontSpring, FontSquirrel, and MyFonts to no avail.

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why do you want this in a font? –  Lauren Ipsum Feb 13 '12 at 11:13
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I would echo this; typically this isn't done as a font but rather as controls within the UI. If you're looking for free buttons there are a multitude (nay, a plethora) of free and affordable controls out on the interwebs. –  lawndartcatcher Feb 13 '12 at 13:02
    
It is incredibly useful to be able to style pictures that would ordinarily be images with CSS -- that's the point. –  verve Feb 13 '12 at 13:42
    
See the following reference: css-tricks.com/examples/IconFont . @lawndartcatcher –  verve Feb 13 '12 at 13:56
    
@verve The site you linked has links to collections of fonts, of which at least one contains the controls you are looking for. Am I missing something here? –  Farray Feb 13 '12 at 16:45
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What about using SVG instead of fonts? Not sure below collection has 'loop once' icon but worth checking it out.

www.thenounproject.com

Also I think Itunes' 'loop once' icon is done with '1' in a circle right?

http://www.alanwood.net/demos/wingdings-2.html go down to 'J' or 'U'

You might try to overlay the 'circled 1' with CSS on top of your loop icon.

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