I do it lots. I carry a 15″ MBP in a Large SaddleSack in one of these 
Crumpler 
sleeves<http://www.crumpler.com/AU/Laptop-Bags/Laptop-Carrying-Cases/School-Hymn-L.html?LanguageCode=EN&SKU=SHN001-G00170>
.

My girlfriend carries her 15″ MBP in a Medium SaddleSack in one of these Ron 
D. Swan 
sleeves<http://www.rondswan.com/products.php?p=29&desc=Ron-D-Swan-Padded-Laptop-Sleeve-Padded-ipad-Sleeve-Macbook-Case>.
 
The sleeve only just fits flat in the bottom of the SaddleSack.

In case it's not clear the laptop sits in the sleeve on the bottom of the 
SaddleSack, then you pile your other stuff on top. I've been doing it twice 
a day for well over a year now with no problems. I far prefer having it sit 
flat on the rack in a saddle bag to my previous arrangement, which was to 
carry it in an Ortlieb pannier where it was able to bounce around 
vertically and laterally (if you see what I mean).

I take the SaddleSack off when I park my bike and carry it into my office. 
It takes about 10 seconds to get it off and maybe 30 to put back on again. 
Ortliebs may be quicker but lose out big time on shape and size to the 
SaddleSacks, in my humble IMHO.

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