This invention includes drilling assemblies, drilling reamer arm assemblies, and methods of drilling. In one implementation, a drilling assembly includes a cutting head apparatus configured to cut into earthen material as the cutting head apparatus is rotated. A drive shaft extends aft of and is configured to rotate the cutting head apparatus. A plurality of reamer arm assemblies projects radially outward of the drive shaft and are mounted for rotation therewith aft of the cutting head apparatus. Individual of the reamer arm assemblies include a radial inner portion extending radially outward of the drive shaft. A radial outer portion connects with and extends radially outward of the radial inner portion. The radial outer portion includes a cutter. At least one breakaway retainer fastens the radial inner and outer portions together and restrains the radial outer portion from moving relative to the radial inner portion towards the cutting head apparatus and the drive shaft. Other aspects are contemplated.