diff --git a/Applications/PaintBrush/EllipseTool.cpp b/Applications/PaintBrush/EllipseTool.cpp
index cbed5ebba6..1517c7065e 100644
--- a/Applications/PaintBrush/EllipseTool.cpp
+++ b/Applications/PaintBrush/EllipseTool.cpp
@@ -115,18 +115,21 @@ void EllipseTool::on_contextmenu(GContextMenuEvent& event)
             m_mode = Mode::Outline;
         }));
         m_context_menu->add_separator();
-        m_context_menu->add_action(GAction::create("1", [this](auto&) {
-            m_thickness = 1;
-        }));
-        m_context_menu->add_action(GAction::create("2", [this](auto&) {
-            m_thickness = 2;
-        }));
-        m_context_menu->add_action(GAction::create("3", [this](auto&) {
-            m_thickness = 3;
-        }));
-        m_context_menu->add_action(GAction::create("4", [this](auto&) {
-            m_thickness = 4;
-        }));
+        m_thickness_actions.set_exclusive(true);
+        auto insert_action = [&](int size, bool checked = false) {
+            auto action = GAction::create(String::number(size), [this, size](auto& action) {
+                m_thickness = size;
+                action.set_checked(true);
+            });
+            action->set_checkable(true);
+            action->set_checked(checked);
+            m_thickness_actions.add_action(*action);
+            m_context_menu->add_action(move(action));
+        };
+        insert_action(1, true);
+        insert_action(2);
+        insert_action(3);
+        insert_action(4);
     }
     m_context_menu->popup(event.screen_position());
 }
diff --git a/Applications/PaintBrush/EllipseTool.h b/Applications/PaintBrush/EllipseTool.h
index dfbd560ec0..09779566d8 100644
--- a/Applications/PaintBrush/EllipseTool.h
+++ b/Applications/PaintBrush/EllipseTool.h
@@ -28,6 +28,7 @@
 
 #include "Tool.h"
 #include <LibDraw/Point.h>
+#include <LibGUI/GActionGroup.h>
 
 class GMenu;
 class Painter;
@@ -58,5 +59,6 @@ private:
     Point m_ellipse_end_position;
     RefPtr<GMenu> m_context_menu;
     int m_thickness { 1 };
+    GActionGroup m_thickness_actions;
     Mode m_mode { Mode::Outline };
 };
diff --git a/Applications/PaintBrush/EraseTool.cpp b/Applications/PaintBrush/EraseTool.cpp
index 76adad6630..cf9737b868 100644
--- a/Applications/PaintBrush/EraseTool.cpp
+++ b/Applications/PaintBrush/EraseTool.cpp
@@ -86,18 +86,22 @@ void EraseTool::on_contextmenu(GContextMenuEvent& event)
 
         m_context_menu->add_action(eraser_color_toggler);
         m_context_menu->add_separator();
-        m_context_menu->add_action(GAction::create("1", [this](auto&) {
-            m_thickness = 1;
-        }));
-        m_context_menu->add_action(GAction::create("2", [this](auto&) {
-            m_thickness = 2;
-        }));
-        m_context_menu->add_action(GAction::create("3", [this](auto&) {
-            m_thickness = 3;
-        }));
-        m_context_menu->add_action(GAction::create("4", [this](auto&) {
-            m_thickness = 4;
-        }));
+
+        m_thickness_actions.set_exclusive(true);
+        auto insert_action = [&](int size, bool checked = false) {
+            auto action = GAction::create(String::number(size), [this, size](auto& action) {
+                m_thickness = size;
+                action.set_checked(true);
+            });
+            action->set_checkable(true);
+            action->set_checked(checked);
+            m_thickness_actions.add_action(*action);
+            m_context_menu->add_action(move(action));
+        };
+        insert_action(1, true);
+        insert_action(2);
+        insert_action(3);
+        insert_action(4);
     }
 
     m_context_menu->popup(event.screen_position());
diff --git a/Applications/PaintBrush/EraseTool.h b/Applications/PaintBrush/EraseTool.h
index 76c1578c68..b7ca11ae8c 100644
--- a/Applications/PaintBrush/EraseTool.h
+++ b/Applications/PaintBrush/EraseTool.h
@@ -28,6 +28,7 @@
 
 #include "Tool.h"
 #include <LibDraw/Point.h>
+#include <LibGUI/GActionGroup.h>
 
 class GMenu;
 
@@ -48,4 +49,5 @@ private:
 
     bool m_use_secondary_color { true };
     int m_thickness { 1 };
+    GActionGroup m_thickness_actions;
 };
diff --git a/Applications/PaintBrush/LineTool.cpp b/Applications/PaintBrush/LineTool.cpp
index 40232a3753..8fcffb0d24 100644
--- a/Applications/PaintBrush/LineTool.cpp
+++ b/Applications/PaintBrush/LineTool.cpp
@@ -131,18 +131,21 @@ void LineTool::on_contextmenu(GContextMenuEvent& event)
 {
     if (!m_context_menu) {
         m_context_menu = GMenu::construct();
-        m_context_menu->add_action(GAction::create("1", [this](auto&) {
-            m_thickness = 1;
-        }));
-        m_context_menu->add_action(GAction::create("2", [this](auto&) {
-            m_thickness = 2;
-        }));
-        m_context_menu->add_action(GAction::create("3", [this](auto&) {
-            m_thickness = 3;
-        }));
-        m_context_menu->add_action(GAction::create("4", [this](auto&) {
-            m_thickness = 4;
-        }));
+        m_thickness_actions.set_exclusive(true);
+        auto insert_action = [&](int size, bool checked = false) {
+            auto action = GAction::create(String::number(size), [this, size](auto& action) {
+                m_thickness = size;
+                action.set_checked(true);
+            });
+            action->set_checkable(true);
+            action->set_checked(checked);
+            m_thickness_actions.add_action(*action);
+            m_context_menu->add_action(move(action));
+        };
+        insert_action(1, true);
+        insert_action(2);
+        insert_action(3);
+        insert_action(4);
     }
     m_context_menu->popup(event.screen_position());
 }
diff --git a/Applications/PaintBrush/LineTool.h b/Applications/PaintBrush/LineTool.h
index c34ab99a5f..b591ffeef5 100644
--- a/Applications/PaintBrush/LineTool.h
+++ b/Applications/PaintBrush/LineTool.h
@@ -28,6 +28,7 @@
 
 #include "Tool.h"
 #include <LibDraw/Point.h>
+#include <LibGUI/GActionGroup.h>
 
 class GMenu;
 
@@ -51,6 +52,7 @@ private:
     Point m_line_start_position;
     Point m_line_end_position;
     RefPtr<GMenu> m_context_menu;
+    GActionGroup m_thickness_actions;
     int m_thickness { 1 };
     bool m_constrain_angle { false };
 };
diff --git a/Applications/PaintBrush/PenTool.cpp b/Applications/PaintBrush/PenTool.cpp
index 873f7ea46f..e670afa97f 100644
--- a/Applications/PaintBrush/PenTool.cpp
+++ b/Applications/PaintBrush/PenTool.cpp
@@ -77,18 +77,21 @@ void PenTool::on_contextmenu(GContextMenuEvent& event)
 {
     if (!m_context_menu) {
         m_context_menu = GMenu::construct();
-        m_context_menu->add_action(GAction::create("1", [this](auto&) {
-            m_thickness = 1;
-        }));
-        m_context_menu->add_action(GAction::create("2", [this](auto&) {
-            m_thickness = 2;
-        }));
-        m_context_menu->add_action(GAction::create("3", [this](auto&) {
-            m_thickness = 3;
-        }));
-        m_context_menu->add_action(GAction::create("4", [this](auto&) {
-            m_thickness = 4;
-        }));
+        m_thickness_actions.set_exclusive(true);
+        auto insert_action = [&](int size, bool checked = false) {
+            auto action = GAction::create(String::number(size), [this, size](auto& action) {
+                m_thickness = size;
+                action.set_checked(true);
+            });
+            action->set_checkable(true);
+            action->set_checked(checked);
+            m_thickness_actions.add_action(*action);
+            m_context_menu->add_action(move(action));
+        };
+        insert_action(1, true);
+        insert_action(2);
+        insert_action(3);
+        insert_action(4);
     }
     m_context_menu->popup(event.screen_position());
 }
diff --git a/Applications/PaintBrush/PenTool.h b/Applications/PaintBrush/PenTool.h
index 431325cf78..3495c23b2a 100644
--- a/Applications/PaintBrush/PenTool.h
+++ b/Applications/PaintBrush/PenTool.h
@@ -28,6 +28,7 @@
 
 #include "Tool.h"
 #include <LibDraw/Point.h>
+#include <LibGUI/GActionGroup.h>
 
 class GMenu;
 
@@ -47,4 +48,5 @@ private:
     Point m_last_drawing_event_position { -1, -1 };
     RefPtr<GMenu> m_context_menu;
     int m_thickness { 1 };
+    GActionGroup m_thickness_actions;
 };
diff --git a/Applications/PaintBrush/SprayTool.cpp b/Applications/PaintBrush/SprayTool.cpp
index defc793022..1a9c9895a5 100644
--- a/Applications/PaintBrush/SprayTool.cpp
+++ b/Applications/PaintBrush/SprayTool.cpp
@@ -103,18 +103,21 @@ void SprayTool::on_contextmenu(GContextMenuEvent& event)
 {
     if (!m_context_menu) {
         m_context_menu = GMenu::construct();
-        m_context_menu->add_action(GAction::create("1", [this](auto&) {
-            m_thickness = 1;
-        }));
-        m_context_menu->add_action(GAction::create("2", [this](auto&) {
-            m_thickness = 2;
-        }));
-        m_context_menu->add_action(GAction::create("3", [this](auto&) {
-            m_thickness = 3;
-        }));
-        m_context_menu->add_action(GAction::create("4", [this](auto&) {
-            m_thickness = 4;
-        }));
+        m_thickness_actions.set_exclusive(true);
+        auto insert_action = [&](int size, bool checked = false) {
+            auto action = GAction::create(String::number(size), [this, size](auto& action) {
+                m_thickness = size;
+                action.set_checked(true);
+            });
+            action->set_checkable(true);
+            action->set_checked(checked);
+            m_thickness_actions.add_action(*action);
+            m_context_menu->add_action(move(action));
+        };
+        insert_action(1, true);
+        insert_action(2);
+        insert_action(3);
+        insert_action(4);
     }
     m_context_menu->popup(event.screen_position());
 }
diff --git a/Applications/PaintBrush/SprayTool.h b/Applications/PaintBrush/SprayTool.h
index fb0441ce1d..8eb13797c5 100644
--- a/Applications/PaintBrush/SprayTool.h
+++ b/Applications/PaintBrush/SprayTool.h
@@ -27,8 +27,9 @@
 #pragma once
 
 #include "Tool.h"
-#include <LibGUI/GPainter.h>
 #include <LibCore/CTimer.h>
+#include <LibGUI/GActionGroup.h>
+#include <LibGUI/GPainter.h>
 
 class GMenu;
 
@@ -49,5 +50,6 @@ private:
     Point m_last_pos;
     Color m_color;
     RefPtr<GMenu> m_context_menu;
+    GActionGroup m_thickness_actions;
     int m_thickness { 1 };
 };