As I recall, the xxWxx ratings are based on oil viscosities at 100 F and 210 F, think 40 C and 100 C now. Synthetic oils will generally have a bigger range of xxWxx numbers than non-synthetic. You can get a synthetic, for instance, that's 0W40. This is a bigger range than any dino oil ever could muster.
At starting temperatures of 20 F down to perhaps as low at -20 F (and further north, even -40 F/C), oil viscosities can really thicken up, particularly if that xxWxx range is smaller.
Someone here mentioned pour point. Oil generally won't pour once it reaches about 1 million centistokes viscosity. Some oils reach this and won't pour. Others solidify due to the presence of wax molecules. Synthetic oils will generally have a lower viscosity at lower temperatures and don't have ANY wax molecules. These properties will help a lot in providing less resistance to flow at starting engine temperatures.
Ralph