diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index a173025cda29..ec421e6da238 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -1900,6 +1900,15 @@ def can_return_none(self, type: TypeInfo, attr_name: str) -> bool:
                     return is_subtype(NoneType(), node.type.ret_type)
         return False
 
+    def _replace_callable_return_type(self, tp: Type, replacement: Type) -> ProperType:
+        """Replace the return type of a callable or overloaded type with replacement."""
+        ptp = get_proper_type(tp)
+        if isinstance(ptp, CallableType):
+            return ptp.copy_modified(ret_type=replacement)
+        if isinstance(ptp, Overloaded):
+            return Overloaded([c.copy_modified(ret_type=replacement) for c in ptp.items])
+        return ptp
+
     def analyze_type_type_callee(self, item: ProperType, context: Context) -> Type:
         """Analyze the callee X in X(...) where X is Type[item].
 
@@ -1932,10 +1941,25 @@ def analyze_type_type_callee(self, item: ProperType, context: Context) -> Type:
             # with typevar.
             callee = self.analyze_type_type_callee(get_proper_type(item.upper_bound), context)
             callee = get_proper_type(callee)
+            # When the TypeVar has a union bound, use the bound as the return type
+            # instead of the TypeVar itself, since calling the constructor should
+            # return an instance of one of the union members.
+            return_type = item
+            upper_bound = get_proper_type(item.upper_bound)
+            if isinstance(upper_bound, UnionType):
+                return_type = upper_bound
             if isinstance(callee, CallableType):
-                callee = callee.copy_modified(ret_type=item)
+                callee = callee.copy_modified(ret_type=return_type)
             elif isinstance(callee, Overloaded):
-                callee = Overloaded([c.copy_modified(ret_type=item) for c in callee.items])
+                callee = Overloaded([c.copy_modified(ret_type=return_type) for c in callee.items])
+            elif isinstance(callee, UnionType):
+                callee = UnionType(
+                    [
+                        self._replace_callable_return_type(tp, return_type)
+                        for tp in callee.relevant_items()
+                    ],
+                    callee.line,
+                )
             return callee
         # We support Type of namedtuples but not of tuples in general
         if isinstance(item, TupleType) and tuple_fallback(item).type.fullname != "builtins.tuple":
diff --git a/mypy/types.py b/mypy/types.py
index d4ed728f4c9b..1ab06a338631 100644
--- a/mypy/types.py
+++ b/mypy/types.py
@@ -2311,6 +2311,15 @@ def type_object(self) -> mypy.nodes.TypeInfo:
         ret = get_proper_type(self.ret_type)
         if isinstance(ret, TypeVarType):
             ret = get_proper_type(ret.upper_bound)
+        if isinstance(ret, UnionType):
+            # When the TypeVar has a union bound, pick the first item's
+            # fallback. This is only used for is_protocol checks, which
+            # are not applicable to union-bound typevars.
+            first = get_proper_type(ret.items[0])
+            if isinstance(first, Instance):
+                ret = first
+            else:
+                ret = self.fallback
         if isinstance(ret, TupleType):
             ret = ret.partial_fallback
         if isinstance(ret, TypedDictType):