diff --git a/sql/src/main/java/org/apache/druid/sql/calcite/rel/DruidQuery.java b/sql/src/main/java/org/apache/druid/sql/calcite/rel/DruidQuery.java
index f24f0381451..1f71a9212cb 100644
--- a/sql/src/main/java/org/apache/druid/sql/calcite/rel/DruidQuery.java
+++ b/sql/src/main/java/org/apache/druid/sql/calcite/rel/DruidQuery.java
@@ -41,7 +41,6 @@ import org.apache.calcite.rex.RexBuilder;
 import org.apache.calcite.rex.RexInputRef;
 import org.apache.calcite.rex.RexNode;
 import org.apache.calcite.sql.SqlKind;
-import org.apache.calcite.sql.type.SqlTypeName;
 import org.apache.calcite.util.ImmutableBitSet;
 import org.apache.druid.java.util.common.ISE;
 import org.apache.druid.java.util.common.Pair;
@@ -64,7 +63,6 @@ import org.apache.druid.query.groupby.orderby.DefaultLimitSpec;
 import org.apache.druid.query.groupby.orderby.OrderByColumnSpec;
 import org.apache.druid.query.operator.WindowOperatorQuery;
 import org.apache.druid.query.ordering.StringComparator;
-import org.apache.druid.query.ordering.StringComparators;
 import org.apache.druid.query.scan.ScanQuery;
 import org.apache.druid.query.timeboundary.TimeBoundaryQuery;
 import org.apache.druid.query.timeseries.TimeseriesQuery;
@@ -209,7 +207,6 @@ public class DruidQuery
     // Now the fun begins.
     final DimFilter filter;
     final Projection selectProjection;
-    final Projection unnestProjection;
     final Grouping grouping;
     final Sorting sorting;
     final Windowing windowing;
@@ -438,6 +435,7 @@ public class DruidQuery
    * @param rowSignature          source row signature
    * @param virtualColumnRegistry re-usable virtual column references
    * @param typeFactory           factory for SQL types
+   *
    * @return dimensions
    *
    * @throws CannotBuildQueryException if dimensions cannot be computed
@@ -625,14 +623,7 @@ public class DruidQuery
         throw new ISE("Don't know what to do with direction[%s]", collation.getDirection());
       }
 
-      final SqlTypeName sortExpressionType = sortExpression.getType().getSqlTypeName();
-      if (SqlTypeName.NUMERIC_TYPES.contains(sortExpressionType)
-          || SqlTypeName.TIMESTAMP == sortExpressionType
-          || SqlTypeName.DATE == sortExpressionType) {
-        comparator = StringComparators.NUMERIC;
-      } else {
-        comparator = StringComparators.LEXICOGRAPHIC;
-      }
+      comparator = Calcites.getStringComparatorForRelDataType(sortExpression.getType());
 
       if (sortExpression.isA(SqlKind.INPUT_REF)) {
         final RexInputRef ref = (RexInputRef) sortExpression;
diff --git a/sql/src/test/java/org/apache/druid/sql/calcite/CalciteJoinQueryTest.java b/sql/src/test/java/org/apache/druid/sql/calcite/CalciteJoinQueryTest.java
index be65a64e80a..ce657219a0c 100644
--- a/sql/src/test/java/org/apache/druid/sql/calcite/CalciteJoinQueryTest.java
+++ b/sql/src/test/java/org/apache/druid/sql/calcite/CalciteJoinQueryTest.java
@@ -5222,7 +5222,7 @@ public class CalciteJoinQueryTest extends BaseCalciteQueryTest
                                                     .filters(new InDimFilter("m2", new HashSet<>(Arrays.asList(null, "A"))))
                                                     .virtualColumns(expressionVirtualColumn("v0", "notnull(\"m2\")", ColumnType.LONG))
                                                     .dimension(new DefaultDimensionSpec("v0", "d0", ColumnType.LONG))
-                                                    .metric(new InvertedTopNMetricSpec(new DimensionTopNMetricSpec(null, StringComparators.LEXICOGRAPHIC)))
+                                                    .metric(new InvertedTopNMetricSpec(new DimensionTopNMetricSpec(null, StringComparators.NUMERIC)))
                                                     .aggregators(new CountAggregatorFactory("a0"))
                                                     .threshold(1)
                                                     .build()
diff --git a/sql/src/test/java/org/apache/druid/sql/calcite/CalciteQueryTest.java b/sql/src/test/java/org/apache/druid/sql/calcite/CalciteQueryTest.java
index 9d5b0e2c52b..4d4fa189107 100644
--- a/sql/src/test/java/org/apache/druid/sql/calcite/CalciteQueryTest.java
+++ b/sql/src/test/java/org/apache/druid/sql/calcite/CalciteQueryTest.java
@@ -8764,6 +8764,61 @@ public class CalciteQueryTest extends BaseCalciteQueryTest
     );
   }
 
+  @Test
+  public void testGroupByOrderByBoolean()
+  {
+    // Not msqCompatible until https://github.com/apache/druid/pull/14046 is merged.
+    testQuery(
+        "SELECT dim1 = 'abc', COUNT(*) FROM druid.foo GROUP BY 1 ORDER BY 1, 2 LIMIT 2",
+        ImmutableList.of(
+            GroupByQuery.builder()
+                        .setDataSource(CalciteTests.DATASOURCE1)
+                        .setInterval(querySegmentSpec(Filtration.eternity()))
+                        .setGranularity(Granularities.ALL)
+                        .setVirtualColumns(
+                            expressionVirtualColumn(
+                                "v0",
+                                "(\"dim1\" == 'abc')",
+                                ColumnType.LONG
+                            )
+                        )
+                        .setDimensions(
+                            dimensions(
+                                new DefaultDimensionSpec(
+                                    "v0",
+                                    "d0",
+                                    ColumnType.LONG
+                                )
+                            )
+                        )
+                        .setAggregatorSpecs(aggregators(new CountAggregatorFactory("a0")))
+                        .setLimitSpec(
+                            new DefaultLimitSpec(
+                                ImmutableList.of(
+                                    new OrderByColumnSpec(
+                                        "d0",
+                                        Direction.ASCENDING,
+                                        StringComparators.NUMERIC
+                                    ),
+                                    new OrderByColumnSpec(
+                                        "a0",
+                                        Direction.ASCENDING,
+                                        StringComparators.NUMERIC
+                                    )
+                                ),
+                                2
+                            )
+                        )
+                        .setContext(QUERY_CONTEXT_DEFAULT)
+                        .build()
+        ),
+        ImmutableList.of(
+            new Object[]{false, 5L},
+            new Object[]{true, 1L}
+        )
+    );
+  }
+
   @Test
   public void testGroupByFloorTimeAndOneOtherDimensionWithOrderBy()
   {