▁however , ▁de formed ▁the ▁bullet ▁and ▁was ▁in ac cur ate . ▁ ▁Square ▁bul lets ▁have ▁orig ins ▁that ▁almost ▁pre - date ▁civil ization ▁and ▁were ▁used ▁by ▁s ling ers ▁in ▁sl ings . ▁They ▁were ▁typically ▁made ▁out ▁of ▁co pper ▁or ▁lead . ▁The ▁most ▁notable ▁use ▁of ▁square ▁bullet ▁designs ▁was ▁done ▁by ▁James ▁P uck le ▁and ▁K yle ▁Tun is ▁who ▁pat ented ▁them , ▁where ▁they ▁were ▁briefly ▁used ▁in ▁one ▁version ▁of ▁the ▁P uck le ▁gun . ▁The ▁early ▁use ▁of ▁these ▁in ▁the ▁black - pow der ▁era ▁was ▁soon ▁dis cont in ued ▁due ▁to ▁irregular ▁and ▁un predict able ▁flight ▁patterns . ▁ ▁Point ed ▁bul lets ▁ ▁Del v igne ▁continued ▁to ▁develop ▁bullet ▁design ▁and ▁by ▁ 1 8 3 0 ▁had ▁started ▁to ▁develop ▁cyl ind ro - con ical ▁bul lets . ▁His ▁bullet ▁designs ▁were ▁improved ▁by ▁Franco is ▁Tam is ier ▁with ▁the ▁addition ▁of ▁" ball ▁gro ov es " ▁which ▁are ▁known ▁as ▁" c annel ures ", ▁ ▁these ▁moved ▁the ▁resistance ▁of ▁air ▁behind ▁the ▁center ▁of ▁gravity ▁of ▁the ▁bullet . ▁▁ ▁Tam is ier ▁also ▁developed ▁progress ive ▁rif ling . ▁The ▁rif le ▁gro ov es ▁were ▁deeper ▁toward ▁the ▁b ree ch , ▁becoming ▁shall ower ▁as ▁they ▁progress ed ▁toward ▁the ▁m uzz le . ▁This ▁causes ▁the ▁bullet ▁to ▁be ▁progress ively ▁m old ed ▁into ▁the ▁gro ov es ▁which ▁increased