diff --git a/python/pyspark/sql/classic/column.py b/python/pyspark/sql/classic/column.py
index c893050872f4..92c57438c739 100644
--- a/python/pyspark/sql/classic/column.py
+++ b/python/pyspark/sql/classic/column.py
@@ -309,12 +309,16 @@ def eqNullSafe(
     def __and__(
         self, other: Union[ParentColumn, "LiteralType", "DecimalLiteral", "DateTimeLiteral"]
     ) -> ParentColumn:
-        return _bin_op("and", self, other)
+        from pyspark.sql.functions import lit
+
+        return _bin_op("and", self, lit(other))
 
     def __or__(
         self, other: Union[ParentColumn, "LiteralType", "DecimalLiteral", "DateTimeLiteral"]
     ) -> ParentColumn:
-        return _bin_op("or", self, other)
+        from pyspark.sql.functions import lit
+
+        return _bin_op("or", self, lit(other))
 
     def __invert__(self) -> ParentColumn:
         return _func_op("not", self)
@@ -322,12 +326,16 @@ def __invert__(self) -> ParentColumn:
     def __rand__(
         self, other: Union[ParentColumn, "LiteralType", "DecimalLiteral", "DateTimeLiteral"]
     ) -> ParentColumn:
-        return _bin_op("and", self, other)
+        from pyspark.sql.functions import lit
+
+        return _bin_op("and", self, lit(other))
 
     def __ror__(
         self, other: Union[ParentColumn, "LiteralType", "DecimalLiteral", "DateTimeLiteral"]
     ) -> ParentColumn:
-        return _bin_op("or", self, other)
+        from pyspark.sql.functions import lit
+
+        return _bin_op("or", self, lit(other))
 
     # container operators
     def __contains__(self, item: Any) -> None:
diff --git a/python/pyspark/sql/tests/test_column.py b/python/pyspark/sql/tests/test_column.py
index ac599fab1357..ecfcae36c955 100644
--- a/python/pyspark/sql/tests/test_column.py
+++ b/python/pyspark/sql/tests/test_column.py
@@ -94,6 +94,14 @@ def test_column_operators(self):
             cs.startswith("a"),
             cs.endswith("a"),
             ci.eqNullSafe(cs),
+            sf.col("b") & sf.lit(True),
+            sf.col("b") & True,
+            sf.lit(True) & sf.col("b"),
+            True & sf.col("b"),
+            sf.col("b") | sf.lit(True),
+            sf.col("b") | True,
+            sf.lit(True) | sf.col("b"),
+            True | sf.col("b"),
         )
         self.assertTrue(all(isinstance(c, Column) for c in css))
         self.assertTrue(isinstance(ci.cast(LongType()), Column))