85mm f/1.2L USM/85mm f/1.8 USM or death.
Those lenses are /the/ standard for head and shoulder portraits.
If you want a bit more than just the head and shoulders, then, the 135mm f/2L USM is unbeatable.
Versatility, the 70-200mm f/2.8L USM or 70-200mm f/2.8L IS II USM are unbeaten.
The 85mm f/1.8 USM is just $350 and is the sharpest tool in my bag. You'll find high end fashion photographers who make covers for Vogue, and the like, use that lens.
For atmosphere, the 35mm f/1.4L USM... oh, my.
The 100mm f/2.8 USM or 100mm f/2.8L IS USM are also great portrait lenses; particularly for isolation of features.
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