diff --git a/mypy/types.py b/mypy/types.py
index 15ae47e341d4..39c0d8f64011 100644
--- a/mypy/types.py
+++ b/mypy/types.py
@@ -1526,12 +1526,31 @@ class TupleType(ProperType):
 
     def __init__(self, items: List[Type], fallback: Instance, line: int = -1,
                  column: int = -1, implicit: bool = False) -> None:
-        super().__init__(line, column)
-        self.items = items
         self.partial_fallback = fallback
+        self.items = items
         self.implicit = implicit
-        self.can_be_true = len(self.items) > 0
-        self.can_be_false = len(self.items) == 0
+        super().__init__(line, column)
+
+    def can_be_true_default(self) -> bool:
+        if self.can_be_any_bool():
+            # Corner case: it is a `NamedTuple` with `__bool__` method defined.
+            # It can be anything: both `True` and `False`.
+            return True
+        return self.length() > 0
+
+    def can_be_false_default(self) -> bool:
+        if self.can_be_any_bool():
+            # Corner case: it is a `NamedTuple` with `__bool__` method defined.
+            # It can be anything: both `True` and `False`.
+            return True
+        return self.length() == 0
+
+    def can_be_any_bool(self) -> bool:
+        return bool(
+            self.partial_fallback.type
+            and self.partial_fallback.type.fullname != 'builtins.tuple'
+            and self.partial_fallback.type.names.get('__bool__')
+        )
 
     def length(self) -> int:
         return len(self.items)
diff --git a/test-data/unit/check-namedtuple.test b/test-data/unit/check-namedtuple.test
index 5d28d78013f4..b95cc96f8115 100644
--- a/test-data/unit/check-namedtuple.test
+++ b/test-data/unit/check-namedtuple.test
@@ -1081,3 +1081,42 @@ t: T
 y: List[T] = [t]
 [builtins fixtures/tuple.pyi]
 [typing fixtures/typing-namedtuple.pyi]
+
+[case testNamedTupleWithBoolNarrowsToBool]
+# flags: --warn-unreachable
+from typing import NamedTuple
+
+class C(NamedTuple):
+    x: int
+
+    def __bool__(self) -> bool:
+        pass
+
+def foo(c: C) -> None:
+    if c:
+        reveal_type(c)  # N: Revealed type is "Tuple[builtins.int, fallback=__main__.C]"
+    else:
+        reveal_type(c)  # N: Revealed type is "Tuple[builtins.int, fallback=__main__.C]"
+
+def bar(c: C) -> None:
+    if not c:
+        reveal_type(c)  # N: Revealed type is "Tuple[builtins.int, fallback=__main__.C]"
+    else:
+        reveal_type(c)  # N: Revealed type is "Tuple[builtins.int, fallback=__main__.C]"
+
+class C1(NamedTuple):
+    x: int
+
+def foo1(c: C1) -> None:
+    if c:
+        reveal_type(c)  # N: Revealed type is "Tuple[builtins.int, fallback=__main__.C1]"
+    else:
+        c  # E: Statement is unreachable
+
+def bar1(c: C1) -> None:
+    if not c:
+        c  # E: Statement is unreachable
+    else:
+        reveal_type(c)  # N: Revealed type is "Tuple[builtins.int, fallback=__main__.C1]"
+[builtins fixtures/tuple.pyi]
+[typing fixtures/typing-namedtuple.pyi]