diff --git a/lib/matplotlib/legend.py b/lib/matplotlib/legend.py
@@ -824,6 +824,8 @@ def _auto_legend_data(self):
             List of `.Path` corresponding to each line.
         offsets
             List of (x, y) offsets of all collection.
+        texts
+            List of the axes bounding boxes of all texts.
         """
         assert self.isaxes  # always holds, as this is only called internally
         ax = self.parent
@@ -838,7 +840,11 @@ def _auto_legend_data(self):
             _, transOffset, hoffsets, _ = handle._prepare_points()
             for offset in transOffset.transform(hoffsets):
                 offsets.append(offset)
-        return bboxes, lines, offsets
+
+        texts = [text.get_window_extent()
+                 for text in ax.texts]
+
+        return bboxes, lines, offsets, texts
 
     def get_children(self):
         # docstring inherited
@@ -1011,7 +1017,7 @@ def _find_best_position(self, width, height, renderer, consider=None):
 
         start_time = time.perf_counter()
 
-        bboxes, lines, offsets = self._auto_legend_data()
+        bboxes, lines, offsets, texts = self._auto_legend_data()
 
         bbox = Bbox.from_bounds(0, 0, width, height)
         if consider is None:
@@ -1027,11 +1033,12 @@ def _find_best_position(self, width, height, renderer, consider=None):
             # XXX TODO: If markers are present, it would be good to take them
             # into account when checking vertex overlaps in the next line.
             badness = (sum(legendBox.count_contains(line.vertices)
-                           for line in lines)
-                       + legendBox.count_contains(offsets)
-                       + legendBox.count_overlaps(bboxes)
-                       + sum(line.intersects_bbox(legendBox, filled=False)
-                             for line in lines))
+                           for line in lines) +
+                       legendBox.count_contains(offsets) +
+                       legendBox.count_overlaps(bboxes) +
+                       legendBox.count_overlaps(texts) +
+                       sum(line.intersects_bbox(legendBox, filled=False)
+                           for line in lines))
             if badness == 0:
                 return l, b
             # Include the index to favor lower codes in case of a tie.

diff --git a/lib/matplotlib/tests/test_legend.py b/lib/matplotlib/tests/test_legend.py
@@ -570,3 +570,38 @@ def test_no_warn_big_data_when_loc_specified():
         ax.plot(np.arange(5000), label=idx)
     legend = ax.legend('best')
     fig.draw_artist(legend)  # Check that no warning is emitted.
+
+
+def test_overlap_no_texts():
+    # test there is no error without text
+    fig, ax = plt.subplots()
+    fig.canvas.draw()
+    legend = ax.legend()
+    fig.draw_artist(legend)
+
+
+def test_overlap_one_text():
+    # test legend doesn't overlap with one text
+    fig, ax = plt.subplots()
+    fig.canvas.draw()
+    ax.text(1, 0, "Text")
+    legend = ax.legend()
+    fig.draw_artist(legend)
+    texts = [text.get_window_extent()
+             for text in ax.texts]
+
+    assert legend.get_window_extent().count_overlaps(texts) == 0
+
+
+def test_overlap_two_texts():
+    # test legend doesn't overlap with two texts
+    fig, ax = plt.subplots()
+    fig.canvas.draw()
+    ax.text(1, 0, "Text")
+    ax.text(0, 1, "Text")
+    legend = ax.legend()
+    fig.draw_artist(legend)
+    texts = [text.get_window_extent()
+             for text in ax.texts]
+
+    assert legend.get_window_extent().count_overlaps(texts) == 0