diff --git a/mypy/meet.py b/mypy/meet.py
index c5d25652d7b3..00e72e178ac9 100644
--- a/mypy/meet.py
+++ b/mypy/meet.py
@@ -249,13 +249,15 @@ def _type_object_overlap(left: ProperType, right: ProperType) -> bool:
         if isinstance(left, TypeType) and isinstance(right, CallableType) and right.is_type_obj():
             return _is_overlapping_types(left.item, right.ret_type)
         # 2. Type[C] vs Meta, where Meta is a metaclass for C.
-        if (isinstance(left, TypeType) and isinstance(left.item, Instance) and
-                isinstance(right, Instance)):
-            left_meta = left.item.type.metaclass_type
-            if left_meta is not None:
-                return _is_overlapping_types(left_meta, right)
-            # builtins.type (default metaclass) overlaps with all metaclasses
-            return right.type.has_base('builtins.type')
+        if isinstance(left, TypeType) and isinstance(right, Instance):
+            if isinstance(left.item, Instance):
+                left_meta = left.item.type.metaclass_type
+                if left_meta is not None:
+                    return _is_overlapping_types(left_meta, right)
+                # builtins.type (default metaclass) overlaps with all metaclasses
+                return right.type.has_base('builtins.type')
+            elif isinstance(left.item, AnyType):
+                return right.type.has_base('builtins.type')
         # 3. Callable[..., C] vs Meta is considered below, when we switch to fallbacks.
         return False
 
diff --git a/test-data/unit/check-expressions.test b/test-data/unit/check-expressions.test
index 2e34bb4b9e5d..ba4120dea75a 100644
--- a/test-data/unit/check-expressions.test
+++ b/test-data/unit/check-expressions.test
@@ -2579,20 +2579,35 @@ Bad in subclasses  # E: Non-overlapping container check (element type: "Type[Bad
 
 [case testStrictEqualityMetaclass]
 # flags: --strict-equality
-from typing import List, Type
+from typing import List, Type, Any
 
 class Meta(type): ...
 class OtherMeta(type): ...
 
 class A(metaclass=Meta): ...
+class B(metaclass=Meta): ...
 class C(metaclass=OtherMeta): ...
 
 o: Type[object]
+a: Type[Any]
+aa: type
 exp: List[Meta]
 
 A in exp
+B in exp
 C in exp  # E: Non-overlapping container check (element type: "Type[C]", container item type: "Meta")
+
 o in exp
+a in exp
+aa in exp
+
+a in [A, B]
+aa in [A, B]
+
+class AA: ...
+class BB: ...
+a in [AA, BB]
+aa in [AA, BB]
 [builtins fixtures/list.pyi]
 [typing fixtures/typing-full.pyi]