제가 보기에는 OnDrawItem Event를 사용하신게 아닌지
모르겠군요.. 그렇다면 루프를 잘못사용하신것같군요..
밑에 제가 약간 수정한걸 참조해보세요~~
이게 원래 질문에 답이 아닐 수도 있겠지요~~~

그럼 즐거운 하루되세요~~

void __fastcall TForm1::ListBox1DrawItem(TWinControl *Control, int Index,
      TRect &Rect, TOwnerDrawState State)
{
  TCanvas *pCanvas = ((TListBox *)Control)->Canvas;
  AnsiString ast = ListBox1->Items->Strings[Index];

  BitBlt( pCanvas->Handle ,Rect.left+15,Rect.top, 50, 15,
          Image1->Canvas-Handle ,0,0 ,SRCCOPY );
  pCanvas->TextOut(Rect.Left+30, Rect.Top+2, ast);

  TCanvas *sCanvas;
  if (ast == "DEFAULT") {
    sCanvas = Image2->Canvas;
  } else if (ast == "AWAY") {
    sCanvas = Image3->Canvas;
  } else if (ast == "NOANSER") {
    sCanvas = Image4->Canvas;
  }
  BitBlt( pCanvas->Handle ,Rect.left+90,Rect.top, 50, 15, sCanvas->Handle ,0,0 ,SRCCOPY );
}