diff --git a/src/playbin.vala b/src/playbin.vala
index 4549202..5e71bec 100644
--- a/src/playbin.vala
+++ b/src/playbin.vala
@@ -237,12 +237,18 @@ public class Playbin : GLib.Object {
     }
 
     public void play () {
-        assert (this.state != PlaybinState.STOPPED);
-        this.state = PlaybinState.PLAYING;
-        debug ("setting state to playing");
-        var ret = this.mpv.set_property_flag("pause", false);
-        if (ret != 0) {
-            debug (@"failed to set state to playing ($(ret)): $(ret.to_string())");
+        if (this.state == PlaybinState.STOPPED) {
+            // allow only when playlist is not empty
+            // and start from the top
+            assert (this._play_queue.get_n_items () > 0);
+            this.select_track (0);
+        } else {
+            this.state = PlaybinState.PLAYING;
+            debug ("setting state to playing");
+            var ret = this.mpv.set_property_flag("pause", false);
+            if (ret != 0) {
+                debug (@"failed to set state to playing ($(ret)): $(ret.to_string())");
+            }
         }
     }
 
diff --git a/src/ui/playbar.blp b/src/ui/playbar.blp
index d44610f..83ef6c6 100644
--- a/src/ui/playbar.blp
+++ b/src/ui/playbar.blp
@@ -119,7 +119,7 @@ template $UiPlaybar: Box {
         Button {
           icon-name: bind $play_pause_icon_name (template.playbin as <$Playbin>.state as <$PlaybinState>) as <string>;
           valign: center;
-          sensitive: bind $playbin_active (template.playbin as <$Playbin>.state as <$PlaybinState>) as <bool>;
+          sensitive: bind $can_press_play (template.playbin as <$Playbin>.state as <$PlaybinState>, template.playbin as <$Playbin>.play_queue_position) as <bool>;
 
           clicked => $on_play_pause_clicked ();
         }
diff --git a/src/ui/playbar.vala b/src/ui/playbar.vala
index a555a12..0b38644 100644
--- a/src/ui/playbar.vala
+++ b/src/ui/playbar.vala
@@ -41,6 +41,10 @@ class Ui.Playbar : Gtk.Box {
         return state != PlaybinState.STOPPED;
     }
 
+    [GtkCallback] private bool can_press_play (PlaybinState state, uint n_items) {
+        return state != PlaybinState.STOPPED || n_items > 0;
+    }
+
     [GtkCallback] private string mute_button_icon_name (bool mute) {
         return mute ? "audio-volume-muted" : "audio-volume-high";
     }