Have you actually typed the column as bool/Boolean? It seems to work
fine for me (unless you are fussy about the casing). Example below. If
the DataTable is "typed" (i.e. SomeDataTable, SomeDataRow etc) rather
than a vanilla DataTable, you can do a lot by monkeying with the
TypeConverter on a per-property basis (I can elaborate if that would be
useful).

Marc

        DataTable dt = new DataTable();
        dt.Columns.Add("Foo", typeof(bool));
        dt.Rows.Add(false);
        dt.Rows.Add(true);
        Application.EnableVisualStyles();
        Application.Run(
            new Form {
                Controls = {
                    new DataGridView {
                        Columns = {
                            new DataGridViewTextBoxColumn {
                                 DataPropertyName = "Foo"
                            }
                        },
                        Dock = DockStyle.Fill,
                        DataSource = dt
                    }
                }
            });