Owned a 30. Nice low light lens on a cropper. not a great portrait lens as it has some barrel distortion, and the fov at 30 is not super flattering for head and neck shots, but good for environmental portraits.
Owned canon 85 1.8 on a cropper and full frame. Yes, its a great value. very sharp and fast focusing. I like it better on the 5D, b/c of shallow dof, and the focal length is a touch too long on the cropper for me.
Owned the simga 105 2.8 macro on a cropper and full frame. Great macro lens, and sharp. However, slow focusing. on a cropper at that focal length and f 2.8, I need IS. not my top 3 choice for a portrait lens.
Own the 70-200 2.8 IS lens. Lovely on the 5D. possibly best all around portrait combination with 5D. A little long on a cropper. but thats just my shooting style.
85 1.2 on full frame. Amazing lens. in a class of its own. I especially like it on the 5D. expensive and not as much flexibility as a zoom.
On a crop, my favorite portrait lens was the tamron 28-75 2.8. I found it plenty sharp (at least my copy) at 2.8 for portrait. also good focal range. If you can swing the money, you can get the canon L. I have the 28-70 and love it. for the extra money you get faster and more accurate focusing, better corner performance esp on full frame, better built, and better color and contrast.
If you are set on primes, my favorites would be sigma 50 1.4, and canon 85 1.8 for the money on a cropper. I did not own a 50-150 cropper zoom (I think both sigma and tokina make a 2.8 zoom in that range) might be worth a look. again at 2.8 in that range I would like to have IS.
If you are doing studio portrait, then buy a zoom. you will be shooting it stopped down anyway.
good luck.