diff --git a/mypy/checker.py b/mypy/checker.py
index 96b55f321a73..3bee7b633339 100644
--- a/mypy/checker.py
+++ b/mypy/checker.py
@@ -1801,7 +1801,8 @@ def check___new___signature(self, fdef: FuncDef, typ: CallableType) -> None:
                 "but must return a subtype of",
             )
         elif not isinstance(
-            get_proper_type(bound_type.ret_type), (AnyType, Instance, TupleType, UninhabitedType)
+            get_proper_type(bound_type.ret_type),
+            (AnyType, Instance, TupleType, UninhabitedType, LiteralType),
         ):
             self.fail(
                 message_registry.NON_INSTANCE_NEW_TYPE.format(
diff --git a/mypy/checkmember.py b/mypy/checkmember.py
index f19a76ec6a34..719b48b14e07 100644
--- a/mypy/checkmember.py
+++ b/mypy/checkmember.py
@@ -410,6 +410,8 @@ def analyze_type_callable_member_access(name: str, typ: FunctionLike, mx: Member
         ret_type = tuple_fallback(ret_type)
     if isinstance(ret_type, TypedDictType):
         ret_type = ret_type.fallback
+    if isinstance(ret_type, LiteralType):
+        ret_type = ret_type.fallback
     if isinstance(ret_type, Instance):
         if not mx.is_operator:
             # When Python sees an operator (eg `3 == 4`), it automatically translates that
diff --git a/mypy/typeops.py b/mypy/typeops.py
index 298ad4d16f8c..d058bb8201d3 100644
--- a/mypy/typeops.py
+++ b/mypy/typeops.py
@@ -319,7 +319,7 @@ def class_callable(
     default_ret_type = fill_typevars(info)
     explicit_type = init_ret_type if is_new else orig_self_type
     if (
-        isinstance(explicit_type, (Instance, TupleType, UninhabitedType))
+        isinstance(explicit_type, (Instance, TupleType, UninhabitedType, LiteralType))
         # We have to skip protocols, because it can be a subtype of a return type
         # by accident. Like `Hashable` is a subtype of `object`. See #11799
         and isinstance(default_ret_type, Instance)
diff --git a/mypy/types.py b/mypy/types.py
index 38c17e240ccf..426d560c2bf7 100644
--- a/mypy/types.py
+++ b/mypy/types.py
@@ -2278,6 +2278,8 @@ def type_object(self) -> mypy.nodes.TypeInfo:
             ret = ret.partial_fallback
         if isinstance(ret, TypedDictType):
             ret = ret.fallback
+        if isinstance(ret, LiteralType):
+            ret = ret.fallback
         assert isinstance(ret, Instance)
         return ret.type
 
diff --git a/test-data/unit/check-classes.test b/test-data/unit/check-classes.test
index 498a2c12b6e8..c0b1114db512 100644
--- a/test-data/unit/check-classes.test
+++ b/test-data/unit/check-classes.test
@@ -472,6 +472,27 @@ class B(A):
     def __new__(cls) -> B:
         pass
 
+[case testOverride__new__WithLiteralReturnPassing]
+from typing import Literal
+
+class Falsy:
+    def __bool__(self) -> Literal[False]: pass
+
+reveal_type(bool(Falsy()))  # N: Revealed type is "Literal[False]"
+reveal_type(int())  # N: Revealed type is "Literal[0]"
+
+[builtins fixtures/literal__new__.pyi]
+[typing fixtures/typing-medium.pyi]
+
+[case testOverride__new__WithLiteralReturnFailing]
+from typing import Literal
+
+class Foo:
+    def __new__(cls) -> Literal[1]: pass # E: Incompatible return type for "__new__" (returns "Literal[1]", but must return a subtype of "Foo")
+
+[builtins fixtures/__new__.pyi]
+[typing fixtures/typing-medium.pyi]
+
 [case testOverride__new__AndCallObject]
 from typing import TypeVar, Generic
 
diff --git a/test-data/unit/fixtures/__new__.pyi b/test-data/unit/fixtures/__new__.pyi
index 401de6fb9cd1..57d3624ce92c 100644
--- a/test-data/unit/fixtures/__new__.pyi
+++ b/test-data/unit/fixtures/__new__.pyi
@@ -12,6 +12,7 @@ class object:
 class type:
     def __init__(self, x) -> None: pass
 
+class float: pass
 class int: pass
 class bool: pass
 class str: pass
diff --git a/test-data/unit/fixtures/literal__new__.pyi b/test-data/unit/fixtures/literal__new__.pyi
new file mode 100644
index 000000000000..971bc39bfff4
--- /dev/null
+++ b/test-data/unit/fixtures/literal__new__.pyi
@@ -0,0 +1,25 @@
+from typing import Literal, Protocol, overload
+
+class object:
+    def __init__(self) -> None: pass
+
+class type:
+    def __init__(self, x) -> None: pass
+
+class str: pass
+class dict: pass
+class float: pass
+class int:
+    def __new__(cls) -> Literal[0]: pass
+
+class _Truthy(Protocol):
+    def __bool__(self) -> Literal[True]: pass
+
+class _Falsy(Protocol):
+    def __bool__(self) -> Literal[False]: pass
+
+class bool(int):
+    @overload
+    def __new__(cls, __o: _Truthy) -> Literal[True]: pass
+    @overload
+    def __new__(cls, __o: _Falsy) -> Literal[False]: pass