ian ▁( S eth ▁Williams ) ▁took ▁the ▁over night ▁shift ▁when ▁Pen ning ton ▁moved ▁to ▁even ings ▁in ▁ 2 0 0 1 . ▁ ▁Less ▁than ▁a ▁year ▁later , ▁Jac or ▁was ▁absor bed ▁by ▁media ▁giant ▁Clear ▁Channel ▁Communic ations ▁( now ▁current ▁owner ▁i He art Media ): ▁the ▁May ▁ 1 9 9 9 ▁sale ▁continued ▁the ▁bu ying ▁f ren zy ▁brought ▁on ▁by ▁controvers ial ▁and ▁far - re aching ▁federal ▁der eg ulation . ▁ ▁Bo ▁Matt he ws ▁( Alex ▁Gut ierre z ), ▁who ▁became ▁program ▁director ▁for ▁WM MS ▁in ▁early ▁ 2 0 0 4 , ▁h ired ▁Max well ▁( Ben jamin ▁Born stein ) ▁that ▁April ▁for ▁a ▁more ▁" person ality - dri ven " ▁afternoon ▁show : ▁The ▁Max well ▁Show ▁gradually ▁evol ved ▁from ▁air ing ▁mostly ▁music ▁to ▁all ▁talk , ▁and ▁by ▁ 2 0 0 9 ▁had ▁become ▁the ▁number ▁one ▁afternoon ▁program ▁in ▁several ▁key ▁dem ograph ics . ▁ ▁Lov eline ▁– ▁West wood ▁One ' s ▁nation ally ▁synd ic ated ▁call - in ▁show ▁hosted ▁by ▁Dr . ▁D rew ▁– ▁a ired ▁week n ights ▁from ▁August ▁ 2 0 0 8 ▁through ▁June ▁ 2 0 1 0 . ▁ ▁WM MS ▁veter an ▁John ▁G orm an ▁has ▁remained ▁a ▁vocal ▁critic ▁of ▁i He art Media ; ▁G orm an ▁commented ▁on ▁the ▁company ' s ▁former ▁Cleveland ▁executive , ▁Kevin ▁M eth