An improved bit assembly for road milling, mining, and trenching equipment includes a streamlined tip assembly that is a combination of conical and cylindrical in shape and devoid of protrusions or annular indentations that might impede the flow of removed material over and around the bit assembly or provide space for removed material to become clogged or imbedded on the tip assembly. The generally cylindrical hollow shank that mounts the bit holder to the bit block includes at least one axially aligned slot along its side wall that allows the side wall to supply radial force to maintain the bit holder in the bit block.