diff --git a/Application/AppController.h b/Application/AppController.h
index 71ca54099..7372caa8d 100644
--- a/Application/AppController.h
+++ b/Application/AppController.h
@@ -29,6 +29,7 @@
 	IBOutlet NSButton *fileButton;
 	IBOutlet NSButton *shuffleButton;
 	IBOutlet NSButton *repeatButton;
+    IBOutlet NSButton *randomizeButton;
 
 	IBOutlet NSTextField *totalTimeField;
 	
diff --git a/Application/AppController.m b/Application/AppController.m
index 479a1b0ae..8eb1ee318 100644
--- a/Application/AppController.m
+++ b/Application/AppController.m
@@ -241,6 +241,7 @@ increase/decrease as long as the user holds the left/right, plus/minus button */
 	[infoButton setToolTip:NSLocalizedString(@"InfoButtonTooltip", @"")];
 	[shuffleButton setToolTip:NSLocalizedString(@"ShuffleButtonTooltip", @"")];
 	[repeatButton setToolTip:NSLocalizedString(@"RepeatButtonTooltip", @"")];
+    [randomizeButton setToolTip:NSLocalizedString(@"RandomizeButtonTooltip", @"")];
 	[fileButton setToolTip:NSLocalizedString(@"FileButtonTooltip", @"")];
 	
 	[self registerHotKeys];
diff --git a/Cog.xcodeproj/project.pbxproj b/Cog.xcodeproj/project.pbxproj
index c9068cd29..f982a592a 100644
--- a/Cog.xcodeproj/project.pbxproj
+++ b/Cog.xcodeproj/project.pbxproj
@@ -151,6 +151,7 @@
 		838491211807F38A00E7332D /* NowPlayingBarView.m in Sources */ = {isa = PBXBuildFile; fileRef = 8384911D1807F38A00E7332D /* NowPlayingBarView.m */; };
 		838491221807F38A00E7332D /* NowPlayingBarController.xib in Resources */ = {isa = PBXBuildFile; fileRef = 8384911E1807F38A00E7332D /* NowPlayingBarController.xib */; };
 		838491231807F38A00E7332D /* NowPlayingBarController.m in Sources */ = {isa = PBXBuildFile; fileRef = 8384911F1807F38A00E7332D /* NowPlayingBarController.m */; };
+		8384913C1808217300E7332D /* randomize.png in Resources */ = {isa = PBXBuildFile; fileRef = 8384913B1808217300E7332D /* randomize.png */; };
 		8399D4E21805A55000B503B1 /* XmlContainer.m in Sources */ = {isa = PBXBuildFile; fileRef = 8399D4E01805A55000B503B1 /* XmlContainer.m */; };
 		83BCB8DE17FC971300760340 /* FFMPEG.bundle in CopyFiles */ = {isa = PBXBuildFile; fileRef = B09E94350D747F7B0064F138 /* FFMPEG.bundle */; };
 		8D11072B0486CEB800E47090 /* InfoPlist.strings in Resources */ = {isa = PBXBuildFile; fileRef = 089C165CFE840E0CC02AAC07 /* InfoPlist.strings */; };
@@ -746,6 +747,7 @@
 		838491201807F38A00E7332D /* NowPlayingBarController.h */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.h; name = NowPlayingBarController.h; path = Window/NowPlayingBarController.h; sourceTree = "<group>"; };
 		838491241807F75D00E7332D /* NowPlayingBarView.h */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.h; name = NowPlayingBarView.h; path = Window/NowPlayingBarView.h; sourceTree = "<group>"; };
 		8384912518080F2D00E7332D /* Logging.h */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.h; path = Logging.h; sourceTree = "<group>"; };
+		8384913B1808217300E7332D /* randomize.png */ = {isa = PBXFileReference; lastKnownFileType = image.png; name = randomize.png; path = Images/randomize.png; sourceTree = "<group>"; };
 		8399D4E01805A55000B503B1 /* XmlContainer.m */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.objc; path = XmlContainer.m; sourceTree = "<group>"; };
 		8399D4E11805A55000B503B1 /* XmlContainer.h */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = sourcecode.c.h; path = XmlContainer.h; sourceTree = "<group>"; };
 		8D1107310486CEB800E47090 /* Info.plist */ = {isa = PBXFileReference; fileEncoding = 4; lastKnownFileType = text.plist; path = Info.plist; sourceTree = "<group>"; };
@@ -964,6 +966,7 @@
 		177EC02D0B8BC2E60000BC8C /* Images */ = {
 			isa = PBXGroup;
 			children = (
+				8384913B1808217300E7332D /* randomize.png */,
 				1778D3AF0F645A190037E7A0 /* missingArt.png */,
 				17B7CF590F5A05EE00A47027 /* pauseBadge.png */,
 				17B7CF5A0F5A05EE00A47027 /* playBadge.png */,
@@ -1837,6 +1840,7 @@
 				1791005F0CB44D6D0070BC5C /* Cog.scriptTerminology in Resources */,
 				17D1B27D0CF8B2830028F5B5 /* cue.icns in Resources */,
 				838491221807F38A00E7332D /* NowPlayingBarController.xib in Resources */,
+				8384913C1808217300E7332D /* randomize.png in Resources */,
 				17D1B27E0CF8B2830028F5B5 /* it.icns in Resources */,
 				17D1B27F0CF8B2830028F5B5 /* pls.icns in Resources */,
 				17D1B2800CF8B2830028F5B5 /* s3m.icns in Resources */,
diff --git a/English.lproj/Localizable.strings b/English.lproj/Localizable.strings
index a26aac07c..1d6072dcf 100644
--- a/English.lproj/Localizable.strings
+++ b/English.lproj/Localizable.strings
@@ -16,6 +16,7 @@
 "InfoButtonTooltip" = "Information on the selected file";
 "ShuffleButtonTooltip" = "Shuffle mode";
 "RepeatButtonTooltip" = "Repeat mode";
+"RandomizeButtonTooltip" = "Randomize playlist";
 "FileButtonTooltip" = "File drawer";
 
 "replayGainAlbumGain" = "The volume level of playback output will be detected through enumeration, \
diff --git a/English.lproj/MainMenu.xib b/English.lproj/MainMenu.xib
index 6df6d2fde..608b4f364 100644
--- a/English.lproj/MainMenu.xib
+++ b/English.lproj/MainMenu.xib
@@ -82,7 +82,7 @@
                                                         <color key="textColor" name="headerTextColor" catalog="System" colorSpace="catalog"/>
                                                         <color key="backgroundColor" name="headerColor" catalog="System" colorSpace="catalog"/>
                                                     </tableHeaderCell>
-                                                    <imageCell key="dataCell" controlSize="small" refusesFirstResponder="YES" alignment="left" imageScaling="proportionallyDown" image="AE428D9F-3521-44E5-A3BF-1E9BBDE889D6" id="1801">
+                                                    <imageCell key="dataCell" controlSize="small" refusesFirstResponder="YES" alignment="left" imageScaling="proportionallyDown" image="5E732869-3394-4A3E-8412-5CE7E623D825" id="1801">
                                                         <font key="font" metaFont="system"/>
                                                     </imageCell>
                                                     <tableColumnResizingMask key="resizingMask" resizeWithTable="YES" userResizable="YES"/>
@@ -502,7 +502,7 @@
                             </connections>
                         </button>
                     </toolbarItem>
-                    <toolbarItem implicitItemIdentifier="F3591DBA-E0EC-4564-896A-C6EFFABC7873" label="Repeat" paletteLabel="Repeat" image="repeat_on" id="1639">
+                    <toolbarItem implicitItemIdentifier="63C54E84-6C1A-42A6-9FB7-1DF922B1C302" label="Repeat" paletteLabel="Repeat" image="repeat_on" id="1639">
                         <nil key="toolTip"/>
                         <size key="minSize" width="24" height="25"/>
                         <size key="maxSize" width="24" height="25"/>
@@ -523,6 +523,22 @@
                             </connections>
                         </button>
                     </toolbarItem>
+                    <toolbarItem implicitItemIdentifier="9674185F-CBA5-459A-99E9-4D4C8C40ED9A" label="Randomize" paletteLabel="Randomize" image="randomize" id="yMV-q5-Hn3" userLabel="Toolbar Item - Randomize">
+                        <nil key="toolTip"/>
+                        <size key="minSize" width="24" height="25"/>
+                        <size key="maxSize" width="116" height="25"/>
+                        <button key="view" verticalHuggingPriority="750" id="VbB-Rd-jZu">
+                            <rect key="frame" x="22" y="14" width="24" height="25"/>
+                            <autoresizingMask key="autoresizingMask" flexibleMaxX="YES" flexibleMinY="YES"/>
+                            <buttonCell key="cell" type="roundTextured" bezelStyle="texturedRounded" image="randomize" imagePosition="only" alignment="center" borderStyle="border" inset="2" id="bJG-BX-OMx" userLabel="Button Cell">
+                                <behavior key="behavior" pushIn="YES" lightByBackground="YES" lightByGray="YES"/>
+                                <font key="font" metaFont="system"/>
+                            </buttonCell>
+                            <connections>
+                                <action selector="shufflePlaylist:" target="207" id="yOV-Dz-IF2"/>
+                            </connections>
+                        </button>
+                    </toolbarItem>
                     <toolbarItem implicitItemIdentifier="NSToolbarCustomizeToolbarItem" id="1645"/>
                 </allowedToolbarItems>
                 <defaultToolbarItems>
@@ -534,6 +550,7 @@
                     <toolbarItem reference="1568"/>
                     <toolbarItem reference="1552"/>
                     <toolbarItem reference="1636"/>
+                    <toolbarItem reference="yMV-q5-Hn3"/>
                     <toolbarItem reference="1639"/>
                     <toolbarItem reference="1552"/>
                     <toolbarItem reference="1629"/>
@@ -1375,6 +1392,7 @@ Gw
                 <outlet property="playlistController" destination="218" id="236"/>
                 <outlet property="playlistLoader" destination="1319" id="1322"/>
                 <outlet property="playlistView" destination="207" id="1257"/>
+                <outlet property="randomizeButton" destination="VbB-Rd-jZu" id="DTQ-9N-yDD"/>
                 <outlet property="repeatButton" destination="1640" id="ff5-9p-1FL"/>
                 <outlet property="showAlbumColumn" destination="1340" id="1350"/>
                 <outlet property="showArtistColumn" destination="1339" id="1349"/>
@@ -1653,7 +1671,7 @@ Gw
         <customObject id="2434" customClass="FeedbackController"/>
     </objects>
     <resources>
-        <image name="AE428D9F-3521-44E5-A3BF-1E9BBDE889D6" width="17" height="17">
+        <image name="5E732869-3394-4A3E-8412-5CE7E623D825" width="17" height="17">
             <mutableData key="keyedArchiveRepresentation">
 YnBsaXN0MDDUAQIDBAUGRkdYJHZlcnNpb25YJG9iamVjdHNZJGFyY2hpdmVyVCR0b3ASAAGGoK8QDwcI
 ExQZHh8qKyw0NzpAQ1UkbnVsbNUJCgsMDQ4PEBESVk5TU2l6ZVYkY2xhc3NcTlNJbWFnZUZsYWdzVk5T
@@ -1744,6 +1762,7 @@ EkASRRJNElASVRJdEmASchJ1EnoAAAAAAAACAQAAAAAAAABKAAAAAAAAAAAAAAAAAAASfA
         <image name="next" width="16" height="16"/>
         <image name="play" width="16" height="16"/>
         <image name="previous" width="16" height="16"/>
+        <image name="randomize" width="16" height="16"/>
         <image name="repeat_on" width="128" height="128"/>
         <image name="shuffle_on" width="16" height="16"/>
         <image name="volume_high" width="13" height="13"/>
diff --git a/Images/randomize.png b/Images/randomize.png
new file mode 100644
index 000000000..6d0be5c6e
Binary files /dev/null and b/Images/randomize.png differ