modules/gui/macosx/UI/VLCLibraryWindowPlaylistView.xib

@@ -53,7 +53,7 @@
                         <rect key="frame" x="0.0" y="0.0" width="510" height="194"/>
                         <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                         <subviews>
-                            <tableView verticalHuggingPriority="750" allowsExpansionToolTips="YES" columnAutoresizingStyle="lastColumnOnly" multipleSelection="NO" autosaveColumns="NO" rowHeight="16" rowSizeStyle="automatic" viewBased="YES" id="Ubg-RS-LWE" customClass="VLCPlaylistTableView">
+                            <tableView verticalHuggingPriority="750" allowsExpansionToolTips="YES" columnAutoresizingStyle="lastColumnOnly" autosaveColumns="NO" rowHeight="16" rowSizeStyle="automatic" viewBased="YES" id="Ubg-RS-LWE" customClass="VLCPlaylistTableView">
                                 <rect key="frame" x="0.0" y="0.0" width="510" height="194"/>
                                 <autoresizingMask key="autoresizingMask" widthSizable="YES" heightSizable="YES"/>
                                 <size key="intercellSpacing" width="3" height="2"/>

modules/gui/macosx/playlist/VLCPlaylistMenuController.h

@@ -28,7 +28,7 @@ NS_ASSUME_NONNULL_BEGIN
 
 @interface VLCPlaylistMenuController : NSObject
 
-@property (readwrite, weak) NSTableView *playlistTableView;
+@property (readwrite, weak, nonatomic) NSTableView *playlistTableView;
 @property (readonly) NSMenu *playlistMenu;
 
 @end

modules/gui/macosx/playlist/VLCPlaylistMenuController.m

@@ -48,6 +48,10 @@
     NSMenuItem *_clearPlaylistMenuItem;
     NSMenuItem *_sortMenuItem;
 }
+
+@property (readwrite, atomic) NSArray<NSMenuItem *> *items;
+@property (readwrite, atomic) NSArray<NSMenuItem *> *multipleSelectionItems;
+
 @end
 
 @implementation VLCPlaylistMenuController
@@ -86,8 +90,44 @@
     _sortMenuItem = [[NSMenuItem alloc] initWithTitle:_NS("Sort") action:nil keyEquivalent:@""];
     [_sortMenuItem setSubmenu:_playlistSortingMenuController.playlistSortingMenu];
 
+    self.items = @[
+        _playMenuItem,
+        _removeMenuItem,
+        _revealInFinderMenuItem,
+        _informationMenuItem,
+        NSMenuItem.separatorItem,
+        _addFilesToPlaylistMenuItem,
+        _clearPlaylistMenuItem,
+        _sortMenuItem
+    ];
+
+    self.multipleSelectionItems = @[
+        _removeMenuItem,
+        NSMenuItem.separatorItem,
+        _addFilesToPlaylistMenuItem,
+        _clearPlaylistMenuItem,
+        _sortMenuItem
+    ];
+
     _playlistMenu = [[NSMenu alloc] init];
-    [_playlistMenu addMenuItemsFromArray:@[_playMenuItem, _removeMenuItem, _revealInFinderMenuItem, _informationMenuItem, [NSMenuItem separatorItem], _addFilesToPlaylistMenuItem, _clearPlaylistMenuItem, _sortMenuItem]];
+    _playlistMenu.itemArray = self.items;
+}
+
+- (void)setPlaylistTableView:(NSTableView *)playlistTableView
+{
+    NSNotificationCenter * const notificationCenter = NSNotificationCenter.defaultCenter;
+    if (self.playlistTableView != nil) {
+        [notificationCenter removeObserver:self
+                                      name:NSTableViewSelectionDidChangeNotification
+                                    object:self.playlistTableView];
+    }
+
+    _playlistTableView = playlistTableView;
+    [notificationCenter addObserver:self
+                           selector:@selector(tableViewSelectionDidChange:)
+                               name:NSTableViewSelectionDidChangeNotification
+                             object:self.playlistTableView];
+
 }
 
 - (void)play:(id)sender
@@ -103,9 +143,6 @@
 
 - (void)remove:(id)sender
 {
-    if (self.playlistTableView.selectedRow == -1)
-        return;
-
     [_playlistController removeItemsAtIndexes:self.playlistTableView.selectedRowIndexes];
 }
 
@@ -180,4 +217,19 @@
     return NO;
 }
 
+- (void)tableViewSelectionDidChange:(NSNotification *)notification
+{
+    NSTableView * const tableView = notification.object;
+    if (tableView != self.playlistTableView) {
+        return;
+    }
+
+    const BOOL multipleSelection = tableView.selectedRowIndexes.count > 1;
+    if (multipleSelection) {
+        self.playlistMenu.itemArray = self.multipleSelectionItems;
+    } else {
+        self.playlistMenu.itemArray = self.items;
+    }
+}
+
 @end

modules/gui/macosx/playlist/VLCPlaylistTableView.m

@@ -30,18 +30,18 @@
 #import "playlist/VLCPlaylistMenuController.h"
 
 @interface VLCPlaylistTableView ()
-{
-    VLCPlaylistMenuController *_menuController;
-}
+
+@property (readonly, atomic) VLCPlaylistMenuController *menuController;
+
 @end
 
 @implementation VLCPlaylistTableView
 
 - (NSMenu *)menuForEvent:(NSEvent *)event
 {
-    if (!_menuController) {
+    if (self.menuController == nil) {
         _menuController = [[VLCPlaylistMenuController alloc] init];
-        _menuController.playlistTableView = self;
+        self.menuController.playlistTableView = self;
     }
 
     NSPoint pt = [self convertPoint: [event locationInWindow] fromView: nil];
@@ -49,7 +49,7 @@
     if (row != -1 && ![[self selectedRowIndexes] containsIndex: row])
         [self selectRowIndexes:[NSIndexSet indexSetWithIndex:row] byExtendingSelection:NO];
 
-    return _menuController.playlistMenu;
+    return self.menuController.playlistMenu;
 }
 
 - (void)keyDown:(NSEvent *)event