diff --git a/examples/misc/logos2.py b/examples/misc/logos2.py
index 528f09e92c18..bae838be6ad0 100644
--- a/examples/misc/logos2.py
+++ b/examples/misc/logos2.py
@@ -20,10 +20,10 @@
 def get_font_properties():
     # The original font is Calibri, if that is not installed, we fall back
     # to Carlito, which is metrically equivalent.
-    if 'Calibri' in matplotlib.font_manager.findfont('Calibri:bold'):
+    if 'Calibri' in matplotlib.font_manager.findfont('Calibri:bold').keys():
         return matplotlib.font_manager.FontProperties(family='Calibri',
                                                       weight='bold')
-    if 'Carlito' in matplotlib.font_manager.findfont('Carlito:bold'):
+    if 'Carlito' in matplotlib.font_manager.findfont('Carlito:bold').keys():
         print('Original font not found. Falling back to Carlito. '
               'The logo text will not be in the correct font.')
         return matplotlib.font_manager.FontProperties(family='Carlito',
diff --git a/examples/text_labels_and_annotations/font_table.py b/examples/text_labels_and_annotations/font_table.py
index e9296430ac13..0ef5877c0d42 100644
--- a/examples/text_labels_and_annotations/font_table.py
+++ b/examples/text_labels_and_annotations/font_table.py
@@ -34,6 +34,7 @@ def print_glyphs(path):
     """
     if path is None:
         path = fm.findfont(fm.FontProperties())  # The default font.
+        path = next(iter(path.values()))  # Get the first filepath
 
     font = FT2Font(path)
 
@@ -60,6 +61,7 @@ def draw_font_table(path):
     """
     if path is None:
         path = fm.findfont(fm.FontProperties())  # The default font.
+        path = next(iter(path.values()))  # Get the first filepath
 
     font = FT2Font(path)
     # A charmap is a mapping of "character codes" (in the sense of a character
diff --git a/lib/matplotlib/_mathtext.py b/lib/matplotlib/_mathtext.py
index 3cc90e1f7501..e9306606d1e6 100644
--- a/lib/matplotlib/_mathtext.py
+++ b/lib/matplotlib/_mathtext.py
@@ -242,6 +242,9 @@ def destroy(self):
     def _get_font(self, font):
         if font in self.fontmap:
             basename = self.fontmap[font]
+            # TODO: allow multiple fonts
+            # for now settle with the first element
+            basename = next(iter(basename.values()))
         else:
             basename = font
         cached_font = self._fonts.get(basename)
diff --git a/lib/matplotlib/backends/_backend_pdf_ps.py b/lib/matplotlib/backends/_backend_pdf_ps.py
index 780e79bf71b8..a66c3d675972 100644
--- a/lib/matplotlib/backends/_backend_pdf_ps.py
+++ b/lib/matplotlib/backends/_backend_pdf_ps.py
@@ -108,6 +108,10 @@ def get_text_width_height_descent(self, s, prop, ismath):
     def _get_font_afm(self, prop):
         fname = font_manager.findfont(
             prop, fontext="afm", directory=self._afm_font_dir)
+
+        # TODO: allow multiple font caching
+        # for now pass the first font
+        fname = next(iter(fname.values()))
         return _cached_get_afm_from_fname(fname)
 
     def _get_font_ttf(self, prop):
diff --git a/lib/matplotlib/backends/backend_pdf.py b/lib/matplotlib/backends/backend_pdf.py
index 10063bd9a7b3..7b60257f90c3 100644
--- a/lib/matplotlib/backends/backend_pdf.py
+++ b/lib/matplotlib/backends/backend_pdf.py
@@ -829,11 +829,16 @@ def fontName(self, fontprop):
 
         if isinstance(fontprop, str):
             filename = fontprop
-        elif mpl.rcParams['pdf.use14corefonts']:
-            filename = findfont(
-                fontprop, fontext='afm', directory=RendererPdf._afm_font_dir)
         else:
-            filename = findfont(fontprop)
+            if mpl.rcParams["pdf.use14corefonts"]:
+                filename = findfont(fontprop, fontext="afm",
+                                    directory=RendererPdf._afm_font_dir)
+            else:
+                filename = findfont(fontprop)
+
+            # TODO: allow multiple fonts for PDF backend
+            # for now settle with the first element
+            filename = next(iter(filename.values()))
 
         Fx = self.fontNames.get(filename)
         if Fx is None:
diff --git a/lib/matplotlib/backends/backend_pgf.py b/lib/matplotlib/backends/backend_pgf.py
index 575d2d263496..457c3fa1a9d5 100644
--- a/lib/matplotlib/backends/backend_pgf.py
+++ b/lib/matplotlib/backends/backend_pgf.py
@@ -50,7 +50,13 @@ def get_fontspec():
         for family, command in zip(families, commands):
             # 1) Forward slashes also work on Windows, so don't mess with
             # backslashes.  2) The dirname needs to include a separator.
-            path = pathlib.Path(fm.findfont(family))
+            path = fm.findfont(family)
+
+            # TODO: Allow multiple fonts
+            # for now stick with the first font
+            path = next(iter(path.values()))
+
+            path = pathlib.Path(path)
             latex_fontspec.append(r"\%s{%s}[Path=\detokenize{%s}]" % (
                 command, path.name, path.parent.as_posix() + "/"))
 
diff --git a/lib/matplotlib/font_manager.py b/lib/matplotlib/font_manager.py
index 9d45575eb13d..2234bf29e37d 100644
--- a/lib/matplotlib/font_manager.py
+++ b/lib/matplotlib/font_manager.py
@@ -23,6 +23,7 @@
 #   - setWeights function needs improvement
 #   - 'light' is an invalid weight value, remove it.
 
+from collections import OrderedDict
 import dataclasses
 from functools import lru_cache
 import json
@@ -1097,7 +1098,9 @@ def addfont(self, path):
     def defaultFont(self):
         # Lazily evaluated (findfont then caches the result) to avoid including
         # the venv path in the json serialization.
-        return {ext: self.findfont(family, fontext=ext)
+
+        # TODO: allow embedding multiple fonts
+        return {ext: next(iter(self.findfont(family, fontext=ext).values()))
                 for ext, family in self.defaultFamily.items()}
 
     def get_default_weight(self):
@@ -1304,16 +1307,38 @@ def findfont(self, prop, fontext='ttf', directory=None,
         rc_params = tuple(tuple(rcParams[key]) for key in [
             "font.serif", "font.sans-serif", "font.cursive", "font.fantasy",
             "font.monospace"])
-        return self._findfont_cached(
-            prop, fontext, directory, fallback_to_default, rebuild_if_missing,
-            rc_params)
+
+        prop = FontProperties._from_any(prop)
+        ffamily = prop.get_family()
+
+        # maintain two dicts, one for available paths,
+        # the other for fallback paths
+        fpaths, fbpaths = OrderedDict(), OrderedDict()
+        for fidx in range(len(ffamily)):
+            cprop = prop.copy()
+
+            # set current prop's family
+            cprop.set_family(ffamily[fidx])
+
+            fpath = self._findfont_cached(
+                FontProperties._from_any(cprop), fontext, directory,
+                fallback_to_default, rebuild_if_missing, rc_params)
+
+            # if fontfile isn't found, fpath will be an OrderedDict
+            if isinstance(fpath, OrderedDict):
+                fbpaths.update(fpath)
+            else:
+                fpaths[ffamily[fidx]] = fpath
+
+        # append fallback font(s) to the very end
+        fpaths.update(fbpaths)
+
+        return fpaths
 
     @lru_cache()
     def _findfont_cached(self, prop, fontext, directory, fallback_to_default,
                          rebuild_if_missing, rc_params):
 
-        prop = FontProperties._from_any(prop)
-
         fname = prop.get_file()
         if fname is not None:
             return fname
@@ -1401,7 +1426,10 @@ def is_opentype_cff_font(filename):
 
 
 @lru_cache(64)
-def _get_font(filename, hinting_factor, *, _kerning_factor, thread_id):
+def _get_font(filenames, hinting_factor, *, _kerning_factor, thread_id):
+    # TODO: allow multiple files (future PR)
+    # for now just pass the first element
+    filename = filenames[0]
     return ft2font.FT2Font(
         filename, hinting_factor, _kerning_factor=_kerning_factor)
 
@@ -1417,11 +1445,20 @@ def _get_font(filename, hinting_factor, *, _kerning_factor, thread_id):
 def get_font(filename, hinting_factor=None):
     # Resolving the path avoids embedding the font twice in pdf/ps output if a
     # single font is selected using two different relative paths.
-    filename = _cached_realpath(filename)
+    if isinstance(filename, OrderedDict):
+        filenames = []
+        for fname in filename.values():
+            filenames.append(_cached_realpath(fname))
+    else:
+        filenames = [_cached_realpath(filename)]
     if hinting_factor is None:
         hinting_factor = rcParams['text.hinting_factor']
+
+    # convert to tuple so its hashable
+    filenames = tuple(filenames)
+
     # also key on the thread ID to prevent segfaults with multi-threading
-    return _get_font(filename, hinting_factor,
+    return _get_font(filenames, hinting_factor,
                      _kerning_factor=rcParams['text.kerning_factor'],
                      thread_id=threading.get_ident())
 
diff --git a/lib/matplotlib/tests/test_font_manager.py b/lib/matplotlib/tests/test_font_manager.py
index 4cad797b3757..d5c9be39c47a 100644
--- a/lib/matplotlib/tests/test_font_manager.py
+++ b/lib/matplotlib/tests/test_font_manager.py
@@ -24,7 +24,8 @@ def test_font_priority():
             'font.sans-serif':
             ['cmmi10', 'Bitstream Vera Sans']}):
         font = findfont(FontProperties(family=["sans-serif"]))
-    assert Path(font).name == 'cmmi10.ttf'
+    # first font should be cmmi10.ttf
+    assert Path(next(iter(font.values()))).name == 'cmmi10.ttf'
 
     # Smoketest get_charmap, which isn't used internally anymore
     font = get_font(font)
@@ -110,7 +111,7 @@ def test_utf16m_sfnt():
 
 def test_find_ttc():
     fp = FontProperties(family=["WenQuanYi Zen Hei"])
-    if Path(findfont(fp)).name != "wqy-zenhei.ttc":
+    if "wqy-zenhei.ttc" not in map(lambda x: Path(x).name, findfont(fp)):
         pytest.skip("Font may be missing")
 
     fig, ax = plt.subplots()
diff --git a/lib/matplotlib/tests/test_mathtext.py b/lib/matplotlib/tests/test_mathtext.py
index 22079ccf9874..63d020963f6e 100644
--- a/lib/matplotlib/tests/test_mathtext.py
+++ b/lib/matplotlib/tests/test_mathtext.py
@@ -225,6 +225,8 @@ def test_mathfont_rendering(baseline_images, fontset, index, text):
 
 def test_fontinfo():
     fontpath = mpl.font_manager.findfont("DejaVu Sans")
+    # get the first element
+    fontpath = next(iter(fontpath.values()))
     font = mpl.ft2font.FT2Font(fontpath)
     table = font.get_sfnt_table("head")
     assert table['version'] == (1, 0)
diff --git a/lib/matplotlib/tests/test_text.py b/lib/matplotlib/tests/test_text.py
index dccb74ba0038..cb1c5d64e288 100644
--- a/lib/matplotlib/tests/test_text.py
+++ b/lib/matplotlib/tests/test_text.py
@@ -27,7 +27,7 @@ def test_font_styles():
     def find_matplotlib_font(**kw):
         prop = FontProperties(**kw)
         path = findfont(prop, directory=mpl.get_data_path())
-        return FontProperties(fname=path)
+        return FontProperties(fname=next(iter(path.values())))
 
     from matplotlib.font_manager import FontProperties, findfont
     warnings.filterwarnings(
@@ -198,6 +198,7 @@ def test_antialiasing():
 
 def test_afm_kerning():
     fn = mpl.font_manager.findfont("Helvetica", fontext="afm")
+    fn = next(iter(fn.values()))
     with open(fn, 'rb') as fh:
         afm = mpl.afm.AFM(fh)
     assert afm.string_width_height('VAVAVAVAVAVA') == (7174.0, 718)
diff --git a/lib/matplotlib/ticker.py b/lib/matplotlib/ticker.py
index 2831069ab222..6e11a5dda818 100644
--- a/lib/matplotlib/ticker.py
+++ b/lib/matplotlib/ticker.py
@@ -483,10 +483,15 @@ def __init__(self, useOffset=None, useMathText=None, useLocale=None):
                         ),
                         fallback_to_default=False,
                     )
+                    # visit all values
+                    ufont = ufont.values()
                 except ValueError:
                     ufont = None
 
-                if ufont == str(cbook._get_data_path("fonts/ttf/cmr10.ttf")):
+                if (
+                    ufont is not None and
+                    str(cbook._get_data_path("fonts/ttf/cmr10.ttf")) in ufont
+                ):
                     _api.warn_external(
                         "cmr10 font should ideally be used with "
                         "mathtext, set axes.formatter.use_mathtext to True"