[Страдалецъ]

Так устроит?

Код:

procedure TForm1.CheckListBox1DrawItem(Control: TWinControl;
  Index: Integer; Rect: TRect; State: TOwnerDrawState);
begin
 CheckListBox1.Canvas.TextRect(Rect, ImageList1.Width*2, Rect.Top, CheckListBox1.Items.Strings[Index]);
 ImageList1.Draw(CheckListBox1.Canvas, Rect.Left, Rect.Top, Index);
end;

Выставите для свойства CheckListBox1.Style := lbOwnerDrawFixed