diff --git a/persistence/sql_smartplaylist.go b/persistence/sql_smartplaylist.go
index a5bb4dad..e0f150bc 100644
--- a/persistence/sql_smartplaylist.go
+++ b/persistence/sql_smartplaylist.go
@@ -183,7 +183,10 @@ func (r dateRule) inTheLast(invert bool) (Sqlizer, error) {
 	}
 	period := time.Now().Add(time.Duration(-24*v) * time.Hour)
 	if invert {
-		return Lt{r.Field: period}, nil
+		return Or{
+			Lt{r.Field: period},
+			Eq{r.Field: nil},
+		}, nil
 	}
 	return Gt{r.Field: period}, nil
 }
diff --git a/persistence/sql_smartplaylist_test.go b/persistence/sql_smartplaylist_test.go
index ca0dbc92..3c181cce 100644
--- a/persistence/sql_smartplaylist_test.go
+++ b/persistence/sql_smartplaylist_test.go
@@ -135,7 +135,7 @@ var _ = Describe("smartPlaylist", func() {
 				Expect(args).To(ConsistOf(BeTemporally("~", expectedValue, delta)))
 			},
 			Entry("in the last", "in the last", "lastPlayed > ?", date.Add(-90*24*time.Hour)),
-			Entry("not in the last", "not in the last", "lastPlayed < ?", date.Add(-90*24*time.Hour)),
+			Entry("not in the last", "not in the last", "(lastPlayed < ? OR lastPlayed IS NULL)", date.Add(-90*24*time.Hour)),
 		)
 
 		It("accepts string as the 'in the last' operator value", func() {